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Top 13 Chesapeake Bay Cruising Destinations

Aug 26, 2020

Top 13 Chesapeake Bay Cruising Destinations

One of the big advantages of owning an inflatable boat is the ability to travel where you want, whenever you want, to enjoy a day of sailing. If you're a Maryland, Virginia, or D.C. resident, you have access to one the world's best cruising destinations, the Chesapeake Bay.

From fishing and national parks to delicious food like crabs and oysters, the Chesapeake Bay has a lot to offer. Covering over 4,000 square miles, there is plenty to explore. Below you'll find the top 13 Chesapeake Bay cruising destinations.

1. St. Michaels

St. Michaels Harbor Maryland

Located on Maryland's Eastern Shore, St. Michael's, Maryland has plenty to offer despite being home to a little over 1,000 people. Home to the Chesapeake Bay Maritime Museum , several art galleries, restaurants, and other historic landmarks, St. Michaels is also a prime cruising destination. Located on the water, St. Michael's is a perfect place to access the Chesapeake and it offers up some wonderful views.

2. Galesville

Located on the western shore of the bay, Galesville is a small town that sits along the West River. A steamship line in Galesville used to connect Annapolis and Baltimore, and the town was once home to many Chesapeake Bay Watermen. It is now a hot spot for pleasure boating and home of the West River Sailing Club and Hartge Yacht Harbor

sailboats oxford, md

Located along the Tred Avon and Choptank Rivers, Oxford, Maryland is home to the Oxford-Bellevue Ferry, the Tred Avon Yacht Club, and the Oxford Museum . The ferry is believed to be the oldest privately owned ferry, with service dating back to 1836. In addition to its local attractions, Oxford access to the Tred Avon and Choptank makes it a great cruising destination for sailors and boaters alike.

Located 40 minutes south of Annapolis, Deale, MD provides many scenic views of the Chesapeake, making it a popular destination with boaters. Home to waterfront bars and open-air crab houses, Deale is perfect for anyone looking to hit the open water for the day and then enjoy a good meal afterwards.

5. Solomons Island

Solomons Island Sunset

Located at the mouth of the Patuxent River, Solomons Island was the home of many 19th century shipyards that supported the local fishing economy. Today, Solomons Island is home to many marinas, seafood restaurants, the Calvert Marine Museum , and the Annmarie Sculpture Garden & Arts Center . Its position along the waterfront make it a prime destination for cruising.

6. Rock Hall 

boat on chesapeake in rock hall maryland

The jewel of the Upper Eastern Shore, Rock Hall, MD is a picturesque cruising destination. Serving as the hub for Kent County's maritime industry, Rock Hall is home to the Rock Hall Yacht Club, over a dozen marinas, various charters, boat rentals, and more! A day of cruising in Rock Hall will give you access to beautiful scenery and plenty of open water to explore.

7. Chestertown

Chestertown Maryland

Located along the Chester River, Chestertown was once one of the six Royal Ports of Entry and considered Maryland's second leading port. Today, Chestertown is home to Washington College, a number or restaurants and historic attractions. Offering a wide range of scenic and historic sailing views, Chestertown is a perfect location for day cruising.

8. Kent Island

Lighthouse Kent Island Chesapeake Bay

The largest island in the Chesapeake, Kent Island, is nestled between Annapolis and the Eastern Shore of Maryland. The Cross Island and South Island trails provide plenty of outdoor activities across the island. For those looking to cruise the open waters, Kent Island offers unique access to the Eastern Bay, Chester River, and the heart of the Chesapeake Bay itself.

9. The Wye River

Wye River Eastern Shore

With easy access to fishing and crabbing destinations, the Wye River is a favorite cruising destination for many. Add in the Wye Island Natural Resource Management Area, and you have a perfect destination for cruising and exploring the outdoors.

10. Baltimore

Canton Waterfront Park Baltimore

Baltimore's Historic Inner Harbor is the mouth of the Patapsco River. With access to a number of marinas, the Inner Harbor is a great launch point for day cruising. Enjoy views of historic Federal Hill and Fort McHenry in the Harbor, and as the Patapsco opens up into the bay, you'll find additional outdoor destinations such as North Point State Park and Fort Smallwood Park.

11. Annapolis

Sailing in Annapolis

Sometimes referred to as the Sailing Capital of the U.S., Annapolis is home to various boat shows, the Naval Academy, and the National Sailing Hall of Fame. Its position along the South River, Severn River, and the Chesapeake Bay make it a great launch point for cruising.

12. Washington DC

Sailing outside of washington DC in Arlington, VA

The beautiful Potomac River runs directly through the Nation's Capital, making Washington, D.C. a prime destination for sailors. With access to historic views in the heart of D.C. to a variety of parks and outdoor destinations, D.C. is a great place to spend a day out on the water.

13. Havre de Grace

Concord Point lighthouse Havre de Grace, Maryland

Sitting at the mouth of the Susquehanna River and the head of the Chesapeake, Havre de Grace is uniquely positioned to several state parks and scenic views including Elk Neck State Park and Susquehanna State Park. With easy access to the water and the outdoors, Havre de Grace is a worthwhile destination for anyone looking to explore the bay.

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Chesapeake Sail Club

Chesapeake Sail Club

Sail the chesapeake bay for the 2024 season, boad creek, deltaville, virginia.

Our home port, Broad Creek, at the mouth of the Rappahannock River, means great destinations on the river and bay are within an easy morning or afternoon sail.

Explore the numerous deep water creeks off the Rappahannock – drop your anchor or berth at the available facilities and explore local villages. Favorites include Urbanna, Topping and Irvington.

Set course for a secluded creek and enjoy the natural beauty and wildlife that only the Chesapeake Bay area can offer, favorites include the Corrotoman and Antipoison.

Sailing Chesapeake Bay from Broad Creek, heading either north or south there are numerous bays, rivers and waterfront towns to visit. Favorites include Fleet’s and Little Bays, Great Wicomoco River area and Mobjack Bay.

Sailing east, across the bay, to the eastern shore, you will find quaint and welcoming towns such as Onancock and Cape Charles.

Solomons, MD and Portsmouth/Norfolk, VA are within a few days of sailing from our Rappahannock home port, when your schedule allows.

What Members are Saying

My daughter and I had a great day sailing yesterday. The friends we took with us had a great day as well. Read more

The CSC Fleet – Our Sailing Yachts

With the start of the 2023 sailing season, club members can sail either Bianca , a Tartan 34 keel/centerboard sloop or Ula, a Freedom 32 – your choice each time you reserve sailing time. Both yachts are well equipped, comfortable cruisers.

CSC's Tartan 34 "Bianca"

sailboat cruising chesapeake bay

The Chesapeake Bay is a spectacular North American cruising ground that was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago. The Algonquian word Chesepiooc, meaning “at a big river” became the source of the name for the estuary now called the Chesapeake.The Chesapeake Bay spans more than 64,000 square miles and is home to 150 major rivers and streams. A true boater’s playground, you will find everything you need. From live music and great tiki bars, to cruising with the kiddos, there’s no shortage of fantastic Chesapeake Bay marinas and fun activities here. Below please find a sample itinerary, complete with marina information, deals and discounts.

Cruising the Chesapeake Bay

From baltimore, md to cape charles, va.

sailboat cruising chesapeake bay

The best of the Baltimore is located just steps off the docks at Harbor East Marina. Located in the heart of the city, the Harbor East area of Baltimore boasts 12 square blocks of fine dining restaurants, world-class hotels, hip lounges, quaint pubs, and the best of national and local shops. In addition to all that Harbor East has to offer, marina guests can walk to all the major attractions at the Inner Harbor, Fell’s Point and Little Italy including the National Aquarium and the Maryland Science Center. A quick cab ride will take sports fans to Oriole Park at Camden Yards and M&T Bank Stadium. From Harbor East Marina, guests are also just a short walk away from all of the major attractions at the Inner Harbor, Fell’s Point and Little Italy. Nestled in the center of it all, Harbor East is your gateway to discovering the best of Baltimore.

A walking tour of historic Annapolis, which is arrayed like spokes in a wheel from the Maryland State House, will delight architectural aficionados. Examples of Federal, Italianate, Georgian, Queen Anne and Greek Revival styles from the colonial period through the early 1900s abound. Good provisioning near the marina is hard to find. The locals’ favorite, Graul’s Market, with excellent produce, meat and fish is a mile and a half away. However, the marina has rental car and taxi services available to help stock up at Trader Joe’s, Whole Foods and Fresh Market. The Annapolis Yacht Basin has fuel and Annapolis Harbor Boat Yard is a full service maintenance yard that is conveniently located on Spa Creek near the historic district.

sailboat cruising chesapeake bay

Rock Hall has everything a boater could wish for from first class service/maintenance facilities, restaurants, a grocery store, and fun events all accessible by bike, on foot, or by the great trolley system that connects all of the marinas. Rock Hall has many antiques and crafts stores including America's Past Antiques, Fishbone's Antiques, Rock Hall Gallery and the Artists of Rock Hall Gallery. You will also find gift stores, jewelry, clothing and accessories including Smilin Jake's Casual Apparel on Main Street. Don't miss Pirates and Wenches weekend aka Fantasy Weekend, which includes a decorated dinghy flotilla and kayak races, Caribbean beach party, treasure hunts, entertainment, contests and games for landlubbers and boaters alike. When looking for a place to grab a bite select from Bay Wolf Restaurant, Harbor Shack with live music on Saturday nights, and Waterman's Crabhouse.

sailboat cruising chesapeake bay

For boaters, the focus of this Eastern Shore town is the Chesapeake Bay Maritime Museum with exhibits, restored vessels and hands-on boatbuilding workshops. It is where James Michener did his primary research for his best selling novel, “Chesapeake,” 40 years ago. The picturesque streets of St. Michaels are perfect to stroll along while looking for lunch or dinner. Topping off provisions is easily done within walking distance of the marina at Olivins, a gourmet grocery, or Acme supermarket. Fuel is available at St. Michaels Marina. Higgin’s Yacht Yard is the last full-service boatyard in existence in town.

sailboat cruising chesapeake bay

Oxford’s main attraction is the town itself. It is one of the oldest towns in Maryland, officially founded in 1683. The charming, tree-lined village is a quiet antidote to the hustle and bustle of city life. The Oxford Market, a convenience store, is the only spot in town to buy any essentials for provisioning. If you need fresh fish and seafood, watch for the watermen when they bring their catch in early in the day. The marina is also a full-service boat yard, with gas and diesel available. Hinckley Yacht Services also has a full-service yard in town. Both Brewer and Hinckley provide quality work and craftsmanship.

sailboat cruising chesapeake bay

Zahniser's Yachting Center is one of the most comprehensive marine facilities on the Chesapeake Bay; Located in the town center of Solomons Island, Maryland, Zahniser's is a full-service marina that blends the beauty of a pristine yacht club and the technical expertise of an award winning repair yard. It's the perfect starting point to enjoy the historic village of Solomons Island, either on foot or by bicycle. A destination not to miss - unwind, relax, and enjoy! The marina also has: WiFi, Courtesy Bicycles, a Recycling Center, a Sail Loft & Canvas Shop, Marine Surveyor, Sailing School & Yacht Charters. The marina can also haul vessels up to 70 tons.

sailboat cruising chesapeake bay

Tangier Island is the home of working watermen who get up well before dawn to get their boats ready for crabbing and oystering. The island is most well known for its soft shell crab, for which it claims to be the world capital. With a total population of about 700, most who live there can trace their ancestry back to a handful of families. The small settlement is unique to the Chesapeake and wandering its lanes is the ideal way to pass the time after lunch or dinner at one of the two local restaurants. And, of course, order soft shell crab and crab cakes. Parks Marina is just across the harbor channel from the many crabbing shacks built on stilts along the shore. The marina is owned and operated by 85-year-old Milton Parks, and is a simple affair with fixed docks, pilings and a faded signboard. Milton gladly offers advice on how to dock in the strong current and, once your boat is tied up, he will spin many a story of the island’s inhabitants and history. Daley & Sons is the only grocery store on the island. There are no repair or fueling services for recreational boaters on Tangier Island, but in a pinch a waterman may be able to provide some assistance.

sailboat cruising chesapeake bay

The Tides Inn Marina, 11 miles from Windmill Point on Carter’s Creek, is one of the most luxurious marinas on the Chesapeake Bay. Once docked on their private peninsula, you will have access to complimentary laundry, excellent shower and bath facilities, van and water taxi services, dining and lounges. The resort has a variety of dining options to choose from, all with their own unique style. Relax and recharge with therapeutic treatments at the Journey Spa, or play golf at the Golden Eagle Golf Course. There is always an array of outdoor activities available including tennis, kayaking, croquet, and complimentary bicycles.

sailboat cruising chesapeake bay

Some cruisers who have visited this revived, historic railroad town on Virginia’s Eastern Shore say it’s one of the Mid-Atlantic’s best-kept secrets. Life is easy in this inviting bayside town, with bikes and golf carts sufficing for transportation and menus heavy with local seafood. With most of its structures built between 1885 and 1920, Cape Charles has one of the largest concentrations of restored late-Victorian and turn-of-the-century buildings on the East Coast. Many of these beautiful structures are now transformed into bed and breakfasts, galleries and specialty boutiques. The Gull Hammock Gourmet Market and Drizzles are two high-quality groceries for additional provisioning. They are adjacent to the historic district and conveniently located on your way back from the beach to your boat. At Cape Charles Yacht Center, yachts have full access to nearby Bay Creek Resort, featuring a Beach Club pool as well as two signature golf courses designed by Jack Nicklaus and Arnold Palmer.

Explore Other Regions

Schooner Woodwind

2024 Sailing Season is coming! See you April 13, 2024!

sailboat cruising chesapeake bay

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

TripAdvisor

Make your sailing experience a memorable one! Sail away with us!

Schooner Woodwind Sailing Cruises

We sail April 19, 2024 to Nov 3, 2024

Sail Selina II

Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md.

a drawing of a face

We Sail April 19,2024 to Nov 3, 2024

Clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

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2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

  • User Ages 21+

St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

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Marriage Proposal Engagement Cruise

♥Getting engaged♥? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to pop the question!

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Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

Sail Selina Swag

Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

sailboat cruising chesapeake bay

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips Lyon Rum

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips raising the sail

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips guests taking a turn at the wheel

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips sailing excursions romantic date night

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips sailing excursions people having fun

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

Experience the ultimate sailing adventure on the Chesapeake Bay with Sail Selina, a true symbol of excellence and commitment to providing the best sailing and boating services - Our passion for sailing has led us to achieve the highest standards and earn a Gold Medal award, representing our unwavering dedication to exceeding our guests' expectations - With a full range of sailing and boating services, including private charters, sunset sails, family-friendly adventures, and wine tastings, Sail Selina offers the highest quality and personalized experiences on the Chesapeake Bay - Fall in love with the stunning natural surroundings, charming towns, and rich history of the Chesapeake Bay, as you sail aboard our well-appointed and comfortable yacht - Book now and discover the unparalleled quality and dedication of Sail Selina, the premier sailing adventure on the Chesapeake Bay!

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Savor the taste of luxury of hand picked wines available on all our St Michaels boat rides. Sail Selina offers both reds and whites, providing the ultimate sailing and wine tasting experience on the Chesapeake Bay - This stunning image showcases the elegant and refined design of Sail Selina's etched wine glasses, a perfect complement to our premium wine tastings and luxurious sailing adventures - With a variety of wine tasting packages to choose from, Sail Selina offers a unique and personalized experience for wine enthusiasts and sailing aficionados alike - Fall in love with the rich flavors and aromas of the finest local and international wines, as you sail in style aboard our comfortable and well-equipped boats - Book now and discover the unrivaled taste of luxury and elegance with Sail Selina, the premier wine tasting and sailing adventure on the Chesapeake Bay

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Experience the ultimate sailing adventure on the Chesapeake Bay with Sail Selina. Our quality has achieved the highest standards and has been rewarded with a quality ribbon, representing our commitment to excellence and dedication to providing the best sailing and boating services – It is a symbol of our passion for sailing and our mission to exceed our guests' expectations - With a full range of sailing and boating services, including private charters, sunset sails, family-friendly adventures, and wine tastings, Sail Selina offers the highest quality and personalized experiences on the Chesapeake Bay - Fall in love with the stunning natural surroundings, charming towns, and rich history of the Chesapeake Bay, as you sail aboard our well-appointed and comfortable yacht - Book now and discover the unrivaled quality and dedication of Sail Selina, the premier sailing adventure on the Chesapeake Bay!

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

sailboat cruising chesapeake bay

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Experience the thrill of the journey with Sail Selina's ship's wheel, the ultimate symbol of adventure and maritime history - This stunning image captures the timeless elegance and authenticity of Sail Selina's ship's wheel, a testament to the classic and refined design of the sailing vessel - With our skilled and experienced crew at the helm, enjoy the excitement and thrill of sailing on the Chesapeake Bay, as you witness the power and precision of the ship's wheel in motion - Fall in love with the rich and storied history of the high seas, and experience the magic of sailing aboard an iconic and timeless wooden sailboat - Book now and discover the wonder of the ship's wheel of Sail Selina, an experience that will transport you to another time and place!

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

Chesapeake Windsail Cruises

Sailing on the bay with Chesapeake Windsail Cruises is a beautiful way to enjoy all the splendors of the waters of the Chesapeake Bay, the Cliffs of Calvert or the beautiful environment of the region, all during a wonderful 2 ½ hour cruise on the Chesapeake Bay.

Chesapeake Windsail Cruises sails out of the beautiful Rod 'n' Reel Resort located in the bay-side town of Chesapeake Beach, Maryland, where you can dine before or after your cruise at the Rod ‘n’ Reel restaurant.

We hope you enjoy browsing our website and find a lot of useful information for your cruise or walking tour .

We hope you enjoy browsing our website and find a lot of useful information for your cruise.

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Sail Chesapeake Bay

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Explore the USA's Largest Estuary and Discover America

Living in North America and looking for a bareboat charter destination close to home? Seeking to experience the natural beauty and the modern lifestyle of the USA? Wanting to vacation under sail but not bothered about snorkeling in clear blue tropical waters? Then take a look at Chesapeake Bay as a destination. 

So convenient for the locals and a fascinating place to visit from all over the world, Chesapeake Bay offers lovely summertime conditions for keen sailors and vacationing families. And all around this extensive sunken river valley are exciting places to explore, from secluded bays to modern cities with just about everything this part of USA has to offer.

sailboat cruising chesapeake bay

It All Starts in Annapolis, America's Sailing Capital

Chesapeake Bay is a vast waterway, 200 miles long draining  64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation. Annapolis is a lovely city that lies at the heart of the region's, some would say the nation's, sailing culture. It is also home of the National Sailing Hall of Fame and US Naval Academy - try to spare the time for a tour.

The Chesapeake's Upper Bay

Sailing out of Annapolis, turn the corner and you are immediately far from the bustle of the city. It doesn't take long to get a sense of the geography here – inlet after countless inlet formed as the sea level rose after the last ice age, beyond which wooded lowlands share the landscape with cultivated farm properties and a generous sprinkling of picturesque settlements.

Head south and a huge expanse of tidewater opens up. Bear northeast and sail under the monstrous dual-span Chesapeake Bay Bridge towards Baltimore, or on the eastern shore Rock Hall and the Chester River.

Rock Hall is a pleasant fishing village that offers an overnighting choice on a marina or at anchor in nearby Swan Creek. Just 15 nautical miles from base, getting to Rock Hall is an easy first day's sail. It's also a convenience stepping-off point for an upriver journey in either direction - to Baltimore's Inner Harbor or Chestertown, both with appeal in their own different ways. If you want to spend longer in the Bay's upper reaches, sail up to the Sassafras River and you can easily fill a week-long itinerary without going south of Annapolis. 

But to see more of this huge Bay with its 11,600 miles of shoreline, you need to head back under the big bridge. Immediately south of  Kent Island is Eastern Bay that brings you into the Wye River area. Here St Michaels is a popular stopover, a waterfront village with excellent marina facilities, shops and restaurants catering for the nautical crowd. St Michaels is also home to the Chesapeake Bay Maritime Museum. A short sail further south are Tilghman Island and Oxford, at the mouth of the Choptank River, setting for James A. Michener's great novel Chesapeake. 

This may well be all you have time to see on your Chesapeake Bay sailing vacation. However if you have longer, continue on south, exploring the eastern shore around Crisfield or crossing to Solomons Island if needing supplies or a marina berth.

The Middle Bay and South

Sail by the mouth of the Potomac River and across the state line into Virginia. Call at Smith or Tangier Island for an appreciation of the Chesapeake way of life and the wonderful natural environment in these parts. Most of the residents of Tangier Island make their living from crabbing, one of the Bay's big industries.

As you proceed south, you may wish to stop over at Deltaville for a berth and supplies, before heading across to the up-market coastal resort are of Cape Charles, with all its amenities for young and old. If time is still on your side, you can go as far as Portsmouth, rent a marina and take off by car to explore the area of Newport News, Norfolk and Virginia Beach.

As you sail back to Annapolis, there are numerous top spots you missed on your way out – Onancock,St Leonard's Creek on the Patuxent, and all those other inviting bays and rivers you observed on the way south. So leave plenty of time to stopover and make your return a leisurely sail.

Around these parts there is many a yachtsperson who will talk about sailing on the Chesapeake. How they've been doing it all their lives and still not been into half the bays and rivers. Head out and find your own special place, perhaps it'll be one that even the locals haven't  come across yet.

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Island Chill Yacht Charters

Chesapeake Boat Cruises

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  • (410) 212-4476

Island Chill Yacht Charters -- Choose the wave!

2-Boat Party - Powerboat and Sailboat

WIth Birthday Celebration Package

Spring is Here! So, Welcome Aboard, 2024!

Island chill yacht charters (icyc), & chesapeake bay yacht charters (cbyc), 'to bring people together to create memories and  strengthen friendships & family connections', new location : 'the marina', 1444 shore drive, edgewater, md 21037 (map), email: [email protected]; [email protected].

Booking portal opens April 1st

Call 410-212-4476 for reservations.

Island Chill Yacht Charters (ICYC) creates the 'Relaxing Excitement of the Islands' on our Chesapeake Bay sail and powerboat private cruises for Families, Friends and Couples. We're conveniently located in historic Londontowne in Edgewater, close to Washington D.C. & Baltimore, and just 6 miles south of Annapolis - the 'Sailing Capital of America!' We're the perfect venue for hot summer days and chill sunsets. Celebrate Birthdays, Anniversaries, Bachelorette Parties, Corporate Retreats - add our 'Sail-E-Bration' special occasion decoration packages! National Holidays and Special Events too. Chose our 43'-sailboat (Therapy), or either our 34'- (Irie Vibes)  or 20'-bow-rider (Tallawah) powerboats for captained cruises along the shores of the South and Rhode Rivers, the magnificent Chesapeake Bay as well as get close to the Thomas Point Shoal Lighthouse. At anchor, enjoy swimming, paddle boards, floating lily pad; sun, beaches, sand bars and islands; even kayak and fishing options too. Endless possibilities - endless fun!

Chesapeake Bay Yacht Charters (CBYC) focuses on Storyteller and Specialty cruises - full of Captain John Smith, historic landmarks, President George Washington, lighthouses, pirates, birds, striped bass, wildlife, blue crabs, ospreys and Chesapeake Bay habitats. You'll be an active participant on Storyteller   charters - it's like you are Sir David Attenborough and Ken Burns for a day! There's also Family and Friends Fishing Charters as well as Full Moon Rising trips. Aqua Creative Studios is a great venue for photo and video shoot productions. We even offer exciting opportunities to Crew on Therapy on Windy-Day sailboat expeditions too! 

  • Irie Vibes :  34' Powerboat ( 6-Guests)
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Aqua Creative Studios:

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So, click the links to see excursion options and what to expect. Call with questions or just go ahead and book our Half-Day, Full-day and Sunset cruises for Families, Adolescents and Kids, Friend-Get-Togethers and Couples Getaways. We're ideal for Special Occasions – Birthdays, Anniversaries, Bachelorette Parties and Graduations (each with add-on 'Sail-E-Bration' Decoration Package options). We're a private and exclusive charter company, so we're happy to customize your cruise! Call us. Catering options too. We also offer Corporate Retreat and Reward packages. We celebrate National Events: Memorial and Labor Day, July 4th fireworks, Mother's Day, Father's Day, Jamaica Day, Canada Day and honor the Blue Angels display over the Naval Academy during Commencement Week in Annapolis. Book early! We also have special 2-and 3-Boat combinations for up to 12- and 16-Guests for Special Occasion celebrations. Some bookings need you to call us directly (410) 212-4476 to give time to organize. Our Aqua Creative Studios are an innovative venue for music video shoots, fashion photo presentations, video features and personal portfolios - we even have equipment: drones, cameras, models and photographers too. So, no travel hassles, no airport chaos, no traffic, no lines, no exorbitant gas prices - just an all fun-adventure-party. 

ICYC and CBYC are unique on the Chesapeake Bay. We'd love to welcome you aboard. 

Please Review: Booking/Reschedule/Cancellation/Refund Policy - Safety Policy - Weather Policy - Motion Sickness Policy - Smoking/Lighters/Vaping Policy - Alcohol/Food Policy - Bathroom/Down-Below Policy - Black-Soled Shoes Policy - FAQs

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Therapy (Up to 6 guests)

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Irie Vibes ( Up to 6 guests)

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Tallawah (Up to 4 guests)

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2-Boat Raft-Up (Up to 12 guests)

2024 Photo Updates

Spring is here.

Our Glebe Creek Cove Ospreys returned on March 11th and immediately reclaimed their nest site. Dad cleaned out the nest and chased off rivals - including some very noisy Canada geese and a rather shocked bald eagle who vanished in a flurry of feathers. Mum arrived a day ago and immediately took residence to guard the nest site on our custom-built piling. She didn't budge even when an inquisitive member of Island Chill Yacht Charters discretely visited (hidden in his car) to take her portrait. We're expecting two eggs very soon. We'll update you on their progress.

Daffodils - Osprey Nest - Therapy

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Osprey Nest - Glebe Creek Cove

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Therapy waits patiently for Spring.....

sailboat cruising chesapeake bay

Mapping Megan

The largest and at most famous estuary in the United States, Chesapeake Bay (or “the Chesapeake”) is truly an extraordinary place. Stretching across six states and the District of Columbia, the Bay watershed never ceases to amaze with its rich history, vital economic importance, and astounding beauty. And the wonders of sailing the Chesapeake Bay could fill a lifetime.

The history, natural beauty and wonderful ecosystem combine to present visitors with endless possibilities, and there’s a new adventure around every corner. However if you only have a limited amount of time to explore, it’s best to get an understanding of what there is on offer before your trip.

The following are a couple of tips for planning your sailing adventure on the bay.

How to Stay (Find Airbnbs & Hotels)

Here is an interactive map of hotels and airbnbs you can book in the Chesapeake area.

Be Realistic

If you try to see everything, it’s likely that you’ll miss a lot. Considering the scale of Chesapeake Bay , you will have to be realistic. It is not somewhere to speed around trying to encompass it all in one visit.

Do it right, and you will enjoy the experience so much more and thereafter, who knows, you may return to continue the adventure.

Sailing CC Royalty free

Remember the Definition of Cruising

To sail about for pleasure in an unhurried or unconcerned fashion, to move leisurely about an area. Let the Bay dictate your pace, stimulate your interest, suggest stops and places to see.

Be flexible in your approach, do plan, but don’t think that the plans cannot be altered once you arrive.

Summers are hot and humid, whereas Spring and Autumn are long, and much more comfortable. Even being on the Bay cannot always provide sufficient respite from the still humidity of the summer months, so be warned.

How to Travel

Cruising can take two forms. You can charter a vessel either bareboat or crewed .

Bareboat – You take charge of the boat yourself and provide the crew, and if you are a competent sailor, then this may heighten the excitement, but it is also less of a vacation and more of an adventure. Don’t forget also the issue of stopovers, are you mooring, docking, or anchoring the boat!

Crewed – the cruiser is manned with a captain and crew, and you can sit back and enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties.

Sailing people in the water royalty free

Itinerary Suggestions

There is simply so much, in a sense too much, to see, so it may be a good starting point to pick a more defined area of the Bay and concentrate on that.

Though you’re looking for variety then sailing the Chesapeake area is a natural cruising route for discovery, made for simply hopscotching from one shore to the next, with things to see, visit, experience, taste and indulge all of your senses at once.

Commonly visited areas include Havre de Grace via the Chesapeake & Delaware Canal built in 1829. Many people choose to visit the inner harbour of Baltimore travelling along the Sassafras River with its steep banks and from there to Rock Hall, a sailors town famed for its seafood; travel from St Michaels to Annapolis, known as the sailing capital of the World ; onward to Oxford on the Trent Avon, a sleepy, quaint and picturesque town, or finally on to Washington DC should the mood take you.

You will find yourself with so many options and avenues of adventure, so many that a sense of spontaneity should be a prerequisite. Whilst you slowly absorb the sights, sounds and scenery as you are cruising, you can smile to yourself and be proud that you chose to sail the Chesapeake Bay.

YOU NEED THESE FOR SAILING: CLICK PHOTO ↓

INSPIRED? PIN THESE TO YOUR TRAVEL PINTEREST BOARDS↓

Click through for tips for planning your sailing adventure on Chesapeake bay.

If You Liked This Post You May Also Like:

Best Sailing Destinations in the British Virgin Islands

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Tasha Hacker on Sailing, Ocean Racing and Traveling by Sea.

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Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind  Waking Up Wild ; a website dedicated to opening your eyes to the wild & natural world.

Committed to bringing you the best in adventure travel from all around the globe, there is no mountain too high, and no fete too extreme! They haven’t been everywhere, but it’s on their list.

Follow their journey on Facebook , Twitter ,  YouTube , Pinterest and Instagram .

20 Comments

' src=

Great post, loved the pics! I’ll definitely try to go to Chesapeake!, I’m the kind of person who don’t want to miss anything but I’ll follow your advice “If you try to see everything, it’s likely that you’ll miss a lot.” and as you said, maybe I could return a second time and try to see everything. Thanks for the info! Pilar http://www.thelifestylehunter.com

' src=

Thanks Pilar! So glad you enjoyed the post :) Yes, definitely recommend to pick a more defined area of the Bay and concentrate on that if it’s your first time visiting – there really is just so much to see and do that it’s better to do a little and enjoy it fully than try to slam out a lot and enjoy it half as much.

Hope you have an amazing time!

' src=

At university I had a friend who was always talking about the wonders of Chesapeake Bay and she made it sound like something I really should do. Many years later, I still haven’t, but your post has reminded me how wonderful it sounded.

So glad we could remind you Sarah! Yes, highly recommend a trip – it’s a beautiful bay with so much to see and do :)

' src=

Great tips! You’re so right about the weather. I live in DC and the summers are unbearable. Sailing in the fall is the best time. Annapolis is my favorite place on the bay.

Thanks Jessica :) Awesome to hear you’re already familiar with sailing on the Bay :)

' src=

I will go for the bareboat one where you have total control. Loved the suggestions and nice pics.

Awesome Gokul! Glad to hear we’ve inspired you to take a trip :) Let us know how you enjoy the Chesapeake

' src=

Really good tips. Would love to do this. I would love to lay out and let someone man the boat.

Thanks Holly – yes, jumping on a crewed boat is great if you’re looking to enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties :)

Happy travels!

' src=

This is my home! I was so excited to see my beautiful corner of the world featured!

What an incredible place to grow up! Not bad having Chesapeake Bay as your backyard :) Awesome!

' src=

Hey Megan, I once got invited on a boat but the trip never ended up going through as the boat needed tons of work and couldn’t get out of the port. This sounds amazing. I’d prefer warm waters in the Caribbean but I imagine seeing this side of the US would be gorgeous as well. Thanks for the post. Cheers, Jack

Hi Jack, thanks for your comment :) Sorry to hear your boat didn’t end up going out on Chesapeake – totally agree that the Caribbean is an incredible spot for sailing too. Very different experience to the Bay but they both make for great sailing :)

' src=

Dear Sir, May 22nd, 2018 I have a 27 ft Bayliner sailboat and I would like to sail from Norfolk to Annapolis and back. I have never done this before but it is something that I really want to try. My daughter lives near Annapolis and is close to the water (West River). I feel that I need some bay sailing but I do know how to sail on lakes (Smith Mountain Lake in VA). I am retired and am a good swimmer. I have no idea as to where one would stop for the night and how long it would take and how safe it is to do this. These are my questions and I would like to talk to your group about lessons and feasibility.

Thanks in advance for your time.

Tim Kute 336-413-6126 [email protected]

Hi Tim, thanks for reaching out. We’re a couple who run a personal blog with tips from our adventures, so unfortunately can’t advise you on things like organizing lessons or your level of experience. I would pose your questions to the team at Annapolis Bay Charters who may be able to offer you more insight. Hope they can help :)

http://www.annapolisbaycharters.net

' src=

Hi, Sailing is a life fun for those who live for sail like me.I really like the Sailing tips you share with those who live for sail. its help the new sailors in sailing and boost the moral of the experienced sailors. i appreciate your efforts. One thing i like to add is that don’t forget to protect your hands during sailing with premium quality sailing Gloves.

Glad to hear from a fellow sailor! Great tip on remembering to include gloves in your kit :)

' src=

Thanks for this. We are thinking of sailing down from Boston to Chesapeake via canal. We have 6-week sabbatical so plenty of time. We would like to avoid the worst of the summer heat/humidity, what would be best time to go in your opinion?

Also, I’ve heard that there are a lot of shallow spots in the bay, we draw 6′, any specific areas to avoid?

Thanks, Sea Fever

Hi David :)

Re best time to head out, I would say anytime from April until June, after that and once it hits July it gets really humid so I would avoid at all costs.

For good anchorage spots and plannig out your trip, check out the Gunkholers guide to the Chesapeake, it’s a cruise planner with suggested itineraries but also has charts and waypoints for anchorages and key locations. It’s always very up to date too :)

Have an amazing trip!

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Discover the World; Discover Yourself. Mapping personal evolution through adventure travel. We are Megan and Mike and have been traveling & blogging since 2007 inspiring travel and change!

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Cruising Sailboats for the Chesapeake Bay

There’s no better way to experience all the Chesapeake has to offer, cruising in a warm breeze with friends and family aboard the Club’s J/32’s, J/105’s, and Beneteau 33.  Being a member of the Club makes this dream a reality – and for far less money than ownership, charters or renting a sailboat.  Take a mini-vacation or an extended cruise with your family and friends using the Club’s cruising sailboats.  Your boat is ready and waiting for you!

Sail Club Level 2 Annual Membership Includes Unlimited Use of:

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Better Sailing

Best Sailing Destinations in Chesapeake Bay

Best Sailing Destinations in Chesapeake Bay

Few places on Earth are as easy and beautiful to sail as the Chesapeake Bay, with its rich maritime history, attractive villages, and innumerable bays, creeks, and anchorages. It’s no secret that Annapolis, MD is America’s Sailing Capital, and it’s home to some of the top sailing spots in the country. The Chesapeake is a body of water that stretches 200 miles from the mouth of the Susquehanna River in Havre de Grace to the Virginia twin capes. It varies from 3 miles wide in the north to 25 miles wide in the south. Its lowest point is 200 feet south of Bloody Point on Kent Islan, despite being notoriously shallow in some of its finest streams and bays. It’s important to note that weather and navigational conditions vary greatly in the Chesapeake Bay. Now, keep reading in order to learn more about the best sailing destinations along the Bay!

Baltimore, Maryland

The Patapsco River empties into Baltimore’s Historic Inner Harbor. The Inner Harbor is a fantastic place to start sailing because it has a lot of marinas. In the Harbor, you can see historic Federal Hill and Fort McHenry, and when the Patapsco opens up into the bay, you’ll find other outdoor attractions including North Point State Park and Fort Smallwood Park. The true city on the northern bay, Baltimore is a must-see when sailing there. Henderson’s Wharf Marina, located in the center of Fells Point, has a great anchorage.

You’re nearby to many of Baltimore’s top pubs, taverns, and music venues. Consider sailing to Smith Island, Worton Creek, and Island Pond, find an anchorage, and relax aboard. In fact, the unlimited possibilities are what you will enjoy most about this body of water. But, note that despite all of the sailing and racing many people do there, they feel like they’ve merely scratched the surface.

Galesville, Maryland

Galesville is a small town on the west bank of the bay situated along the West River. This lovely town used to have a steamship line that ran between Annapolis and Baltimore, and it was previously home to numerous Chesapeake Bay watermen. The West River Sailing Club and Hartge Yacht Harbor are now located there, making it a popular site for leisure boating. Galesville is located at the end of Route 255, which becomes Galesville Road and then Main Street as you travel deeper onto the little peninsula. Main Street comes to an end at the water’s edge, where there is a small community park with a 14-mile boardwalk along Riverside Drive on the West River.

Wye River, Maryland

This is one of the most tranquil and bucolic places in the Bay. When sailing there, the place will instantly make you forget the city life. The Wye is a 16-mile-long tributary that surrounds Wye Island, a 2,800-acre nature preserve. Wye Island, on the Miles River’s northern shore, is home to bald eagles and great blue herons. It also features “Schoolhouse Woods,” the Eastern Shore’s biggest intact stretch of old-growth forest. The Wye also has several additional magnificent protected creeks and bays where you may drop a line and find your own little heaven. It’s advisable to take your dinghy and go exploring. Along the island’s lonely shoreline, there’s an almost infinite supply of isolated picnic-perfect beaches.

Chesapeake Bay Maryland Sailing Destination

Solomons Island, Maryland

Solomons Island, located at the mouth of the Patuxent River, was home to multiple 19th-century shipyards that supported the local fishing industry. Many marinas, seafood restaurants, the Calvert Marine Museum, and the Annmarie Sculpture Garden & Arts Center are on Solomons Island today. Its riverside location makes it a popular cruising destination. At the confluence of the Bay and the Patuxent River, Solomons Island is a small, working fishing town. Solomons Island has quickly become a favorite among sailors due to its abundance of activities. Calvert Cliffs and the Drum Point Screwpile Lighthouse offer fantastic restaurants and stores, as well as fossil collecting. To get the most out of your voyage, set aside two days, stopping in Harrington Harbor on the way down and St. Michaels on the way back.

Potomac River

Bay cruisers know Solomons is a beautiful destination with excellent marinas, restaurants, and a fantastic maritime museum, as well as a suitable staging place for crossing the Potomac. It’s about 40 miles south of Solomons to the next harbor, either Reedville or Tangier. When the wind resists the current at the mouths of the rivers in the Chesapeake, the water can become “lumpy.” When the current and wind is in opposition, the Potomac’s mouth should be acknowledged as the Bay’s major tributary. Ducking into Tangier Sound through Hoopers Strait or Kedges Strait and visiting the Eastern Shore will be a more comfortable trip in such conditions.

This route will take you to some of the most isolated and underdeveloped portions of the Lower Eastern Shore. You will also find innumerable lovely and secluded anchorages and several little villages worth seeing, such as Deale Island, Onancock, and Crisfield. The picturesque Pocomoke River, which makes its way through a cypress swamp, may be accessed from Crisfield. This is a truly magical location. There will be no noises of human activity if you turn off your engine.

Saint Michaels, Maryland

In St. Michaels, there are many marinas, a protected anchorage, a launch service, and great restaurants and pubs. The town is arguably one of the most attractive and popular on the bay. The Chesapeake Bay Maritime Museum is St. Michaels’ crown jewel. Many permanent displays at the museum illustrate the geological, social, and economic history of the Chesapeake Bay from the dawn of sail through the period of steam and diesel-powered ships. A great variety of vintage boats are always on display at the museum’s piers, and people are routinely invited onboard for short cruises on the Miles River. In addition, St. Michaels has seen a bit of a gastronomic explosion in recent years, and it now boasts some very good, fashionable new restaurants. For example, 208 Talbot is a terrific spot to go for a casual, relaxing supper in a pleasant setting.

Tilghman Creek, Maryland

If you can’t find a berth for the night after a long day sailing to St. Michaels, you might not want to push into the port. This is particularly true if you are not passing through Kent Narrows. Tilghman Creek is located on the Eastern Bay, just around the corner from Rich Neck. Claiborne is a little settlement at the head of the creek. There is a couple of workboats moored nearby. There are also a few houses along the creek. Despite the seeming availability of space, you should avoid anchoring near the creek itself to prevent interfering with the watermen who leave early in the morning.

Tilghman Creek, Maryland Sailing

Annapolis, Maryland

Annapolis, also known as the US Sailing Capital, is home to a number of boat shows, and the National Sailing Hall of Fame. Its location along the South River, Severn River, and the Chesapeake Bay make it an excellent sailing launch point. Annapolis is one of the bay’s most historic and well-preserved waterfront cities. You could spend days wandering here, with the beautiful Maryland Statehouse, the Governor’s Mansion, the classic and traditional Naval Academy, and the twisting lanes and old maritime mansions. Pussers Caribbean Grille, which overlooks Spa Creek, is one of the area’s traditional pubs. Note that you can rent a mooring ball in one of the marinas in Back Creek. Lastly, getting around Annapolis is not hard because there’s a water taxi service.

Delaware Bay, Delaware

Delaware City is located on the northern end of the Delaware Bay, about 1/2 mile north of the C&D Canal’s Eastern entrance. It is a small community that may be reached on foot from the Delaware City Marina. The Cohansey River is located just southeast of where the Delaware Bay meets the Delaware River. The river is a shallow salt marsh at the Bay entry to the Cohansey. As one moves upstream, the river gets increasingly forested. The salt marsh location has excellent anchoring in terms of water depth and swing space.

Philadelphia, the City of Brotherly Love, is roughly 35 NM east of the canal entry. The entrance to the Christina River and the Port of Wilmington is about 10 miles up the river. Lewes, a beautiful hamlet across the bay from the Cape May Canal, is only 12 miles away. At the bridge that spans the canal and goes to the beach, you will find the city dock. The west end of the Cape May Canal, where the Cape May-Lewes Ferry terminal is located, is where the approach to the harbor from Delaware Bay begins.

Note that before crossing Delaware Bay, you should carefully check the weather forecast. This vast, wide, and exposed body of water is located in the Southeast to Northwest direction. Don’t get me wrong: it’s a great ride in good weather. In this stretch, however, you just have to be cautious! It’s advisable to stay in port if the conditions seem unpleasant for sailing.

Delaware Bay Sailing

Deltaville, Virginia

The majority of the boats heading south from Solomons easily cross the Potomac, stopping in Reedville or Deltaville, Virginia. The rivers and creeks of Virginia’s Northern Neck lie between these two attractions. You’ll know you’re in the Southern Chesapeake whether you choose the larger waters of the Great Wicomico or the well-protected shelter of Mill Creek. Both hurricane holes and anchorages are open to summer breezes in Dividing Creek. Also, note that Hughlett Point State Park’s sandy beaches are accessible from this location.

Experienced Southern Bay sailors will tell you one thing about Stingray Point, which marks the southern end of the Rappahannock River’s entry. They’ll tell you to keep your depth and not wander too close to the mark at first. Expect nice marinas with amenities and maritime services in Deltaville, which is a bit more spread out than other towns with a charming center to meander through. Carter Creek is located on the far side of the Rappahannock River Bridge on the northern side of the river, sometimes known as the “northern neck.” The Chesapeake Restaurant & Terrace offers a unique touch on coastal cuisine for casual dining.

Tangier Island, Virginia

Tangier Island is a must-see on any Southern Bay voyage. You will dock at Parks Marina in Tangier during your stay. Note that Tangier’s sole industry is seafood. For 350 years, the island’s economy has been based on crabbing, oystering, and fishing. Tangier Island’s main street, lined with crab shanties, many of which are built on stilts over the water, provides a view of the working Chesapeake that has vanished from almost every other harbor. The island is a significant soft crab provider. Tangier History Museum and Cultural Interpretive Center is the most prominent museum dedicated to the lives of Chesapeake Bay watermen.

Peter

Peter is the editor of Better Sailing. He has sailed for countless hours and has maintained his own boats and sailboats for years. After years of trial and error, he decided to start this website to share the knowledge.

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Best Sailing Destinations Chesapeake Bay

Best Sailing Destinations Chesapeake Bay | Life of Sailing

Last Updated by

Daniel Wade

May 9, 2023

‍ Key Takeaways

  • The best sailing destinations in the Bay will vary based on your desired water activity
  • A sailing trip in the Bay offers scenic views with great food and rich maritime culture
  • Annapolis is the sailing capital of the world and gives Florida a run for its money
  • Choosing the right boat is key to ensuring a safe travel and comfortable experience
  • Summer months might be crowded so be sure to research the best opportunity for you

‍ Arguably one of the best sailing destinations, Chesapeake Bay, boasts beautiful scenery. But what are some of the best Chesapeake Bay sailing destinations?

The best sailing destinations in Chesapeake Bay are Annapolis and St. Michaels along with Norfolk. Other locations worth checking out are Solomons Island and Rock Hall as well as Smith Island. Keep in mind you need to travel the eastern shore of Maryland and Virginia to see all of these locations.

In my experience there is not much that compares to sailing in Chesapeake Bay. Annapolis is America’s sailing capital of the world for a good reason and is a great place to start.

Table of contents

‍ The Top 15 Best Sailing Destinations in Chesapeake Bay

Chesapeake Bay is quite popular for showcasing the natural beauty and a rich marine history. It has turned into a global sailing destination that offers plenty of exciting experiences for sailors of all kinds.

You can explore many top locations for a sailing adventure but it is recommended to start around Annapolis in Maryland since it is dubbed the sailing capital. Annapolis in general features picturesque villages and plenty of water locations to explore. Keep in mind that weather and navigational conditions vary across the bay.

Annapolis in Maryland is the renowned sailing capital for a good reason. It enchants sailors with the United States Naval Academy and has a rich marine history that features the famous Annapolis Boat Show.

Annapolis offers a lot of opportunities for sailors to dock and explore. This Chesapeake Bay harbor town allures with its scenic beauty. Below you can see other key attractions to this area.

  • Abundant amenities to meet your needs
  • Bustling harbor filled with marinas and boatyards
  • Tons of restaurant possibilities

St. Michaels

St. Michaels has turned into a charming location due to its history and abundant sailing community. Be sure to bring a camera along this eastern shore town that showcases a beautiful harbor and Victorian homes. The town also is home to the Chesapeake Bay Maritime Museum where you can dedicate you time to check out the rich history and vibrant culture of the bay and its waterways.

Norfolk is a bustling harbor city on the Chesapeake Bay's southern coast that boasts a rich naval history as the site of the world's largest naval base. Sailors flock to this cultural hub that is renowned for various options below.

  • Museums with rich history
  • World-class restaurants

Numerous marinas throughout these cruising destinations grant convenient access to sheltered waters. This creates an opportunity for exciting city explorations.

Solomons Island

Solomons Island is another charming and historic town in southern Maryland that sits on the Patuxent River near the Chesapeake Bay. Its protected harbor attracts many sailors and its waterfront park and lighthouse offer scenic beauty.

There are an array of restaurants and shops to check out while staying at one of many marinas. Solomons Island proudly welcomes visitors to explore and unwind.

Rock Hall can be found on Chesapeake Bay's eastern shore where you will likely see an entire village of people fishing. It is loved by many for its natural elegance and wonderful waters.

Sailors that are drawn to crabbing or fishing experiences will want to stop here. The Chesapeake Bay Environmental Center is another additional location to check out since it offers educational programs to enlighten those about its history.

Deltaville offers fully equipped marinas and comprehensive maritime services that are complemented by a charming center for delightful strolls. Solomons' southbound boats often cross the Potomac River while navigating Virginia's Northern Neck rivers and creeks to reach Reedville or Deltaville in Virginia. Explore the vast waters of Great Wicomico or seek shelter in the protected haven of Mill Creek and capture the essence of the Southern Chesapeake.

Smith Island

Smith Island is a perfect sailing location. Those that are wanting to visit this Chesapeake Bay island must visit by boat since it is the only habitable island in Maryland.

There are three different villages in this location but they each offer clear waters and a calm sailing experience. This island is also famous for its Smith Island Cake.

Wye River has a combination of urban and marine areas that allow you to find peaceful surroundings. Wye Island and its 2,800-acre nature preserve are remarkable features that you cannot find anywhere else.

Tuckahoe State Park is one of these beautiful locations that you can check out after sailing. You also have a good chance to see amazing creatures in their natural habitats such as a bald eagle or blue heron. If you have a small enough boat you can explore more areas that are not accessible with larger sailboats.

Tangier Island

Tangier Island is in the Chesapeake Bay's south and is home to serious fishing opportunities. It is also home to the Tangier History Museum that will allow you to check out the island's culture.

There are plenty of boat tours that you could take to experience crabbing or fishing trips if you do not want to on your own boat. The area has secluded waters that make a great escape from reality.

Onancock is another Chesapeake Bay town considered a gem on the Virginia eastern shore. They too have a historic allure and that is coveted by a scenic harbor with a vibrant cultural heritage.

If you are wanting to experience a feeling like home then Onancock is a great opportunity. They have a tight knit community that engages in a lot of fishing and sailing. You can also see a beautiful sunset from many of the docks of your choosing.

Delaware Bay

Delaware City is located at the northern tip of Delaware Bay . This small community can be reached on foot from Delaware City Marina. This used to be a shallow salt marsh but the river becomes more wooded as you go upstream and offers a secure anchoring location with sufficient water depth and swinging space.

The western end of Cape May Canal marks the start of the harbor approach from Delaware Bay.

This expansive and exposed body of water stretches in a Southeast to Northwest direction. Before crossing Delaware Bay it is crucial to carefully check the weather forecast and can be an exhilarating journey under favorable conditions but caution is necessary in this particular area.

Kent Island

Kent Island is located in the heart of the Bay and shows off tons of rich marine history. It is surrounded by sheltered waters and it draws in sailors from all over the world.

You can find the Chesapeake Bay Bridge on this island which is a remarkable feat of architecture that connects the Bay's eastern and western shores. The harbor is a great place to hang out and to enjoy some of the best views for a perfect sunset.

Galesville is a delightful bay town on the west bank that once served as a steamship line hub connecting Annapolis and Baltimore. It was also home to numerous Chesapeake Bay watermen.

You will now see that the area is a sought-after destination for leisure boating with the West River Sailing Club and Hartge Yacht Harbor. This small peninsula offers a charming community park that features a 14-mile boardwalk along Riverside Drive and shows off scenic views of the West River.

Reedville is a charming fishing village at Chesapeake Bay's northern tip. It has a rich maritime history and thriving fishing industry to compliment the serene haven which lures sailing enthusiasts to its pristine waters.

When you explore the scenic harbor you can also check out these options below.

  • Local boutiques
  • Famous eateries
  • Captivating heritage of the Chesapeake Bay's fishing traditions

The Patapsco River flows into Baltimore's Historic Inner Harbor and is an ideal starting point for sailing with numerous marinas. Explore the Harbor to admire landmarks like Federal Hill and Fort McHenry.

As the Patapsco opens up into the bay you can discover outdoor attractions such as North Point State Park and Fort Smallwood Park. Baltimore is a must-visit city for sailors that offers Henderson's Wharf Marina in Fells Point for a convenient anchorage near top pubs or taverns and music venues. There are abundant sailing and racing activities along with other limitless opportunities that might leave you feeling that you have only scratched the surface.

Key Benefits and Drawbacks of Sailing in Chesapeake Bay

Sailing in the Chesapeake Bay’s beautiful waters is a sight you have to see. The experience is definitely worth the trouble but some sailors could argue there are some drawbacks. Below are some of the common pros and cons to consider before sailing in the Bay.

  • There are plenty of sailing locations to help you find a perfect experience. Each spot has its own appeal catered to sailing, fishing, or food.
  • The Bay is famously known for its cuisine. You cannot miss out on the crab cakes and oysters but there are other options too if you do not like fresh seafood.
  • There are plenty of secluded waters to explore. This offers sailors the perfect sailing environment no matter where they plan to go.
  • You will find many marine historic sites and landmarks. This is a perfect opportunity for history buffs to brush up.
  • You will be able to see various forms of wildlife like dolphins and bald eagles.
  • There are a handful of expensive overnight dockage fees at certain Bay marinas that increase the cost of sailing in the area compared to other destinations.
  • The Bay's sailing experience is impacted by environmental challenges like pollution and overfishing. This raises concerns about its quality but actions are being taken to currently help clean up the environment.
  • Navigating certain areas of the Bay can be challenging. The summer typically has an increase of recreational boats and often creates crowded waters.
  • The Bay endures demanding weather with strong winds and rough waters at certain times of the year. This is especially difficult in the winter months.
  • Certain sailing spots within the Bay may offer limited access to essential amenities like grocery stores or repair facilities. You should also check in advance to be close to medical services in the event of any issues.

Ideal Boat Types to Sail in the Chesapeake Bay

Choosing the right boat is important for a safe and enjoyable sailing experience in Chesapeake Bay. Your ideal boat type will correlate on your needs and desires as well as the sailing conditions.

It is best if you conduct proper research based on your needs and the boat type you may already have. If you happen to be in the area you could also chat with local sailors to get their opinion.

Chesapeake Bay typically has these popular boat types:

  • Daysailers are a perfect boating option designed for casual sailing. Those that are new to sailing generally gravitate to this boat type.
  • Cruisers are an appealing sailboat type that offers a comfortable ride and speed. They also offer both relaxation and excitement. These are larger than daysailers but still easy to handle.
  • Catamarans: This multihull boat provides stability and speed while also remaining comfortable. This allows for swift travel and tons of room on the boat for large groups.
  • Center Console Boats are versatile options for anyone that wants to go fishing and cruising. They are usually small enough to go exploring Chesapeake Bay's inlets and coves. They also provide excellent visibility and handling no matter your experience level.

Why You Should Sail in the Chesapeake Bay

Choosing to sail in the Bay could lead to an unforgettable opportunity. There is more than a day’s worth of things to do in any location that you choose.

Appealing Scenery

There are not too many locations that you can sail to that have a balance between urban or city life and sailing. You will be able to see a lot more than people that do not have boats and the tours can only provide so much.

Calm Environment

Chesapeake Bay offers calm waters most of the time but checking the weather conditions is always best before making the trip. It does not matter if you are a first time boat owner or experienced sailor the weather will impact your performance. Thankfully the Bay has dependable weather.

Exciting Opportunities

Whether it is your first time sailing or you are visiting again the Bay offers endless opportunities. These could be fishing or crabbing and maybe even a new restaurant to try out. All of the locations have different historical aspects as well.

Best Memories

In combination of taking the opportunity to explore you will be making some of the best sailing memories. There is a reason why Annapolis is the center for sailing and the Bay is a perfect representation that offers the perfect package.

Related Articles

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

by this author

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Northern Chesapeake Cruising Club (NC3) is a sailing club with interests in cruising, learning and safety. We welcome all people of all ages with an interest in sailing.

Each of us started out not knowing a thing about boats and sailing. Everyone has to start somewhere. Why not start with us?

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Southern New Jersey Fishing Report- March 21, 2024

Schoolie stripers and white perch take bloodworms in the bays and rivers, meanwhile, some anglers are focused on finding winter flounder in Barnegat Bay.

sailboat cruising chesapeake bay

Southern New Jersey Fishing Report

Spring has sprung, but I guess the weather didn’t get the memo this week as we received a chillier week that we have been getting.  The stripers have been on the feed the prior week with dry conditions and multiple days with temperatures up to the 70’s.  Some areas were having bass chase and hit worked artificials, but back with colder temperatures and a slight cool down of bay temps – we are back to the bait and wait game.  White perch and winter flounder have been picking up bloodworms, along with grass shrimp in certain locations.  The winter flounder action has been spotty, mainly because of lack of participation.  But the countdown has begun, only six more weeks until the opening of fluke season.  

Here is this week’s rundown: 

Hook House Bait & Tackle in Toms River has been restocking the shelves for the upcoming spring season.  The shop is loaded with bloodworms, nightcrawler, and tanks full of shiners for freshwater and saltwater.  Schoolie striped bass and some white perch are being caught along the Toms River out to the Route 37 bridge.  Island beach has had some sporadic bird action, but mostly on Atlantic herring and slow on the striped bass front.  There have been a few striped bass caught along the backside rocks off the Barnegat Inlet.  

Creekside Outfitters in Waretown reported striped bass action from Graveling Point to the Toms River with schoolies and a few 29 inch fish being caught on jumbo-sized bloodworms.  Anglers throwing soft plastics are not seeing consistent action as of yet.  White perch have been chewing in parts of the Mullica and the Toms River.  A few hardy souls have ventured out to do some bay side clamming and rewarded with 50-60 clams.  The shop also heard of a few winter flounder being landed on bloodworm.  

Reel Reaction Sportfishing out of Waretown has the backwater skiff ready to go for striped bass action on the flats and some of the skipper’s choice areas.  The larger boat is having routine engine maintenance completed and should be ready for the slip in the next two weeks.  Most weekends have been completely booked out, and there are dates available from mid June through September.  

The Super Chic out of Barnegat Light has been performing their scheduled painting, engine maintenance, and other duties in preparation for the sea bass season.  The vessel will be targeting sea bass for the season opener in May.  The skipper has mentioned that they may plan to get it in for the start of the tautog season in April.  

Tony’s Bait & Tackle in Manahawkin said the hot white perch bite has been occurring in the areas around the Mullica River and additional reports coming from the Toms River.  A few locals have been fishing the areas behind Beach Haven West, but only finding a small pick of perch.  Striped bass are being caught in multiple locations with the western side of Barnegat bay having the best bites.  Most of the fish have been in the 18 to 24 inch size range and caught on bloodworm or small soft plastics.   

Tackle Direct in Egg Harbor City had reports of white perch hitting the banks of the Mullica River and some of the areas up to Lower bank and Green bank on grass shrimp.  Bloodworms has been working on white perch, but better for striped bass.  Graveling Point has had a few bass caught as well as areas from Atlantic City south through Stone Harbor.   

Tight Lines Bait & Tackle in Somers Point received local reports of striped bass, white perch, and even some winter flatties in the backbays of Great Bay and the Mullica River.  Angler participation has been sparse, but of the few that have been going rods have been bent with multiple species.  The shop received a shipment of bloodworms and has clam chum for winter flounder species.  Some of the area bridges are supporting schoolie striped bass on the outgoing tides with small soft plastics or drifted bloodworms.    

Badfish Charters in Ocean City has been working on the vessel and has ran a few scouting runs to the striped bass grounds.  The skipper has found a few areas with cooperative schoolie striped bass as shallow as three feet.  The crew is booking trips for 2024, so give them a ring or message on Instagram.  

Want to get in on the bite? Find an OTW-approved Charter Fishing Captain in New Jersey!  

The Cape May and Fortescue area has mostly smaller sized striped bass from the Cohansey River on bloodworms and also some white perch.  Bloodworms has been the best bait of choice for these.  The Fortescue beach area has given up a few striped bass up to 34 inches on live bloodworm and clam baits.  The beaches of Cape May have been slow, but hopefully with some warmer weather in the coming weeks that changes.  Most boats are being worked on in preparation for the upcoming spring season.  

South Jersey Fishing Forecast

The best bet for this weekend is to find inside activities on Saturday as it looks like the congruence of low pressure systems might dump buckets of rain on us.  It’s a perfect day to hit the “honey do’s”, work on gear, or hit one of the local tackle shops.  Anglers looking to get out may encounter dirty water with all of the rain run-off from the predicted weather for Sunday.  But if you want to give it a go, pick up bloodworms or grass shrimp and go searching for striped bass or white perch along some of the rivers.  In terms of fishability, Friday may be the best day to hit the bays as I’m sure striped bass, winter flounder, and white perch may be on the feed ahead of the weekends wet weather. Good luck, Be Safe, and Tight Lines! 

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Cruising the Moskva River: A short guide to boat trips in Russia’s capital

sailboat cruising chesapeake bay

There’s hardly a better way to absorb Moscow’s atmosphere than on a ship sailing up and down the Moskva River. While complicated ticketing, loud music and chilling winds might dampen the anticipated fun, this checklist will help you to enjoy the scenic views and not fall into common tourist traps.

How to find the right boat?

There are plenty of boats and selecting the right one might be challenging. The size of the boat should be your main criteria.

Plenty of small boats cruise the Moskva River, and the most vivid one is this yellow Lay’s-branded boat. Everyone who has ever visited Moscow probably has seen it.

sailboat cruising chesapeake bay

This option might leave a passenger disembarking partially deaf as the merciless Russian pop music blasts onboard. A free spirit, however, will find partying on such a vessel to be an unforgettable and authentic experience that’s almost a metaphor for life in modern Russia: too loud, and sometimes too welcoming. Tickets start at $13 (800 rubles) per person.

Bigger boats offer smoother sailing and tend to attract foreign visitors because of their distinct Soviet aura. Indeed, many of the older vessels must have seen better days. They are still afloat, however, and getting aboard is a unique ‘cultural’ experience. Sometimes the crew might offer lunch or dinner to passengers, but this option must be purchased with the ticket. Here is one such  option  offering dinner for $24 (1,490 rubles).

sailboat cruising chesapeake bay

If you want to travel in style, consider Flotilla Radisson. These large, modern vessels are quite posh, with a cozy restaurant and an attentive crew at your service. Even though the selection of wines and food is modest, these vessels are still much better than other boats.

sailboat cruising chesapeake bay

Surprisingly, the luxurious boats are priced rather modestly, and a single ticket goes for $17-$32 (1,100-2,000 rubles); also expect a reasonable restaurant bill on top.

How to buy tickets?

Women holding photos of ships promise huge discounts to “the young and beautiful,” and give personal invitations for river tours. They sound and look nice, but there’s a small catch: their ticket prices are usually more than those purchased online.

“We bought tickets from street hawkers for 900 rubles each, only to later discover that the other passengers bought their tickets twice as cheap!”  wrote  (in Russian) a disappointed Rostislav on a travel company website.

Nevertheless, buying from street hawkers has one considerable advantage: they personally escort you to the vessel so that you don’t waste time looking for the boat on your own.

sailboat cruising chesapeake bay

Prices start at $13 (800 rubles) for one ride, and for an additional $6.5 (400 rubles) you can purchase an unlimited number of tours on the same boat on any given day.

Flotilla Radisson has official ticket offices at Gorky Park and Hotel Ukraine, but they’re often sold out.

Buying online is an option that might save some cash. Websites such as  this   offer considerable discounts for tickets sold online. On a busy Friday night an online purchase might be the only chance to get a ticket on a Flotilla Radisson boat.

This  website  (in Russian) offers multiple options for short river cruises in and around the city center, including offbeat options such as ‘disco cruises’ and ‘children cruises.’ This other  website  sells tickets online, but doesn’t have an English version. The interface is intuitive, however.

Buying tickets online has its bad points, however. The most common is confusing which pier you should go to and missing your river tour.

sailboat cruising chesapeake bay

“I once bought tickets online to save with the discount that the website offered,” said Igor Shvarkin from Moscow. “The pier was initially marked as ‘Park Kultury,’ but when I arrived it wasn’t easy to find my boat because there were too many there. My guests had to walk a considerable distance before I finally found the vessel that accepted my tickets purchased online,” said the man.

There are two main boarding piers in the city center:  Hotel Ukraine  and  Park Kultury . Always take note of your particular berth when buying tickets online.

Where to sit onboard?

Even on a warm day, the headwind might be chilly for passengers on deck. Make sure you have warm clothes, or that the crew has blankets ready upon request.

The glass-encased hold makes the tour much more comfortable, but not at the expense of having an enjoyable experience.

sailboat cruising chesapeake bay

Getting off the boat requires preparation as well. Ideally, you should be able to disembark on any pier along the way. In reality, passengers never know where the boat’s captain will make the next stop. Street hawkers often tell passengers in advance where they’ll be able to disembark. If you buy tickets online then you’ll have to research it yourself.

There’s a chance that the captain won’t make any stops at all and will take you back to where the tour began, which is the case with Flotilla Radisson. The safest option is to automatically expect that you’ll return to the pier where you started.

If using any of Russia Beyond's content, partly or in full, always provide an active hyperlink to the original material.

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THE 10 BEST Moscow Boat Rides & Cruises

Boat rides & cruises in moscow.

  • Boat Rentals
  • Scuba & Snorkeling
  • Fishing Charters & Tours
  • Water Sports
  • Stand-Up Paddleboarding
  • Surfing, Windsurfing & Kitesurfing
  • Kayaking & Canoeing
  • Waterskiing & Jetskiing
  • Parasailing & Paragliding
  • River Rafting & Tubing
  • Dolphin & Whale Watching
  • Speed Boats Tours
  • Submarine Tours
  • 5.0 of 5 bubbles
  • 4.0 of 5 bubbles & up
  • 3.0 of 5 bubbles & up
  • 2.0 of 5 bubbles & up
  • 3rd Transport Ring (TTK)
  • District Central (TsAO)
  • Garden Ring
  • District Northern (SAO)
  • Good for Big Groups
  • Good for Couples
  • Good for a Rainy Day
  • Budget-friendly
  • Good for Kids
  • Hidden Gems
  • Honeymoon spot
  • Good for Adrenaline Seekers
  • Adventurous
  • Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.

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1. Flotilla Radisson Royal

JCW703

2. Moscow River Boat Tours

DarshanaBR

3. Sup-Club

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4. Akvanavt Diving Centre

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5. Diving Center Crocus City Oceanarium

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6. CheapRussia Tours

MilosSerb

7. Kite School Kiteclass

T8298GDjuliac

8. SUP Center

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9. Erwin. Reka

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6 ultimate island-hopping itineraries for 2024

Explore the world from the deck of your own yacht with a skippered charter, bareboat or flotilla holiday. Whether you’re a first-timer, a foodie or a family, there’s a sailing itinerary to suit every type of traveller.

sailboat cruising chesapeake bay

Craving a holiday with the freedom to escape the crowds and explore hidden coves, secluded bays and uninhabited islands? Dreaming of anchoring somewhere to take a dip without another person in sight? Sailing enables you to access remote spots that are often inaccessible by land and to experience the diversity of a region, exploring islands, villages and resorts in a single trip. Whether you're just starting out, or keen to set out with little ones in tow, these itineraries suit every type of sailor.  

1. Best for first timers: British Virgin Islands (BVIs)

Calm seas, sheltered anchorages, reliable steady trade winds and easy line-of-sight sailing make the BVIs one of the world’s best sailing destinations for less experienced sailors. The proximity of its islands also means you only need to sail for an hour or two to gain a sense of adventure and achievement as you successfully navigate to the next port of call. Set sail in Tortola and continue on to Virgin Gorda to witness The Baths, a geological wonder made up of granite boulders that stretch down the beach into the sea. Look out for hawksbill turtles as you sail on to tiny specks of land such as the idyllic Saba Rock, and be sure to end the day with a rum cocktail or two at one of the region’s many laid-back bars, which are often perched on unblemished stretches of white sand.

sailboat cruising chesapeake bay

2. Best for families: Croatia

The calm, clear waters of the Adriatic combined with favourable weather conditions in summer provide easy sailing for families and, with more than 1,000 islands dotted along the Dalmatian Coast, there’s a range of activities and attractions with short hops to keep kids engaged. Set sail from the picturesque marina village of Agana and cruise gently to islands such as Brač, Šolta and Hvar, encouraging children to help out on board while keeping an eye out for passing dolphins. With their sheltered bays and clear waters, these islands are ideal stops for families. Spend an afternoon paddling in Brač’s Bobovišća Bay, before setting sail for the remote islands of the Kornati Archipelago, a wild and beautiful national park known for its empty hiking trails. Sailing stops here can be educational, too, with a plethora of UNESCO World Heritage Sites and picturesque port towns steeped in history.

3. Best for food-lovers: Italy

Why base yourself on land to sample Italy’s incredible gastronomy when you can sail from region to region tasting the very best food and wine at numerous ports of call? Sunsail’s SailEatalia’s Italian Cuisine Procida Flotilla departs from the glamourous port town of Procida and sails to the Pontine Islands along the sun-soaked Amalfi Coast, offering stops to taste local cuisine, from classic dishes to regional delicacies as well as the country’s finest wine. Sample Ischia's iconic stewed rabbit in an independent restaurant at the top of a mountain or try the Italian coastal delicacy alici da portare (pasta with anchovies, olives and capers) in the quaint fishing village of Cetara.

sailboat cruising chesapeake bay

4. Best for winter sun: Antigua

Gloriously warm weather between December and May and around 365 powdery white beaches lapped by clear waters make Antigua a popular winter sun destination for British travellers. Sailors can also relax knowing the region has consistent trade winds, safe anchorages and fairly short distances between ports, giving you more time to explore a variety of attractions at your own pace. Drop anchor in Deep Bay to snorkel around the famous shipwreck the Andes , discover uninhabited islands and visit famous places like Nelson’s Dockyard to sip cocktails and dance to the lively music of traditional steel bands.  

5. Best for culture vultures: Croatia  

A cultural treasure trove with 10 UNESCO World Heritage Sites ranging from Roman fortresses to hilltop castles, Croatia is a mecca for sailors with a penchant for history and art. Start and finish a week’s charter in Dubrovnik to explore one of the best-preserved medieval walled cities on Earth, touring ancient citadels and Renaissance palaces, and be sure to include Lokrum, home to the ruins of a Benedictine monastery. Sail north and discover Mljet National Park and the island getaway of Korčula, thought to be the birthplace of famed explorer Marco Polo, where museums, galleries and excellent restaurants line the beautiful cobbled streets and defensive walls of the town.  

sailboat cruising chesapeake bay

6. Best for island-hopping: Greece

With thousands of islands scattered fairly close together, sailing from one to another is a breeze with the promise of a remote white sand or perfect pebble beach around every headland. Sailors are spoilt for choice, but the Ionian Islands, off the west coast of the mainland, are ideal for beginners looking for tranquil stretches of gin-clear water with light winds and warm temperatures in summer. Sail to Ithaca or Kefaloni in the south or to Lefkas, Paxos, Antipaxos and Corfu. While Corfu is known for its party vibe and high-end beach bars, others, like tiny Antipaxos, feature just a scattering of houses, no proper roads and a couple of charming waterside tavernas where you can watch local fishermen bring in the day's catch.  

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Naples man, Bonita Springs woman die in Little Hickory Bay boat crash in North Naples

sailboat cruising chesapeake bay

Two Southwest Florida residents died on Friday in a boat crash that remains under investigation by the Florida Fish and Wildlife Conservation Commission.

John C. Moulder and Judy M. Eaton, both 71, suffered fatal injuries when the 21' Cobia Open Bay boat they were on crashed into the mangrove trees near Little Hickory Bay, Florida Fish and Wildlife said in a statement.

Moulder was from Naples and Eaton was from Bonita Springs.

Moulder and Eaton were the only occupants of the boat and no other vessels were involved in the crash, Florida Fish and Wildlife said.

Eaton was found in the trees and pronounced dead at the scene, while Moulder died from his injuries in a local hospital after being recovered from the water.

Collier had no boating death s in 2021 or 2022, according to the most recent statistical report released by Florida Fish and Wildlife.

Authorities have not released any further information as the investigation continues.

IMAGES

  1. The Chesapeake Bay's Great Cruising Destinations

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  2. Sailing Cruises in Annapolis, Maryland on the Schooner Woodwind on the

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  3. sail boat on the chesapeake bay

    sailboat cruising chesapeake bay

  4. Island-Chill-Yacht-Charters Sailboat-rentals-on-the-Chesapeake-bay-md

    sailboat cruising chesapeake bay

  5. Sailing On The Chesapeake Bay Photograph by Paul Pobiak

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  6. Sailing On

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VIDEO

  1. Cruising Chesapeake Bay 2017(1/2)

  2. Sailing life on the Chesapeake Bay! #boat #sailing #chesapeake

  3. BlueJacket 1: Chesapeake and Delaware Bay

  4. Sailing the Chesapeake Bay, Ep 3: Middle River

  5. Sailing the Chesapeake Bay, Ep 8: Saint Michaels

  6. Exploring Big Major Cay and Staniel Cay, Ep-204

COMMENTS

  1. Top 13 Chesapeake Bay Cruising Destinations

    11. Annapolis. Sometimes referred to as the Sailing Capital of the U.S., Annapolis is home to various boat shows, the Naval Academy, and the National Sailing Hall of Fame. Its position along the South River, Severn River, and the Chesapeake Bay make it a great launch point for cruising. 12.

  2. The Chesapeake Bay's Great Cruising Destinations

    It has that special magic to ease the urban working grind and get you into a Chespeake Bay frame of mind. The Wye is a 16-mile-long tributary that encircles a 2,800-acre wildlife refuge, Wye Island. Located on the northern shore of the Miles River, Wye Island is rife with bald eagles and great blue herons.

  3. Sail the Chesapeake Bay

    With the start of the 2023 sailing season, club members can sail either Bianca, a Tartan 34 keel/centerboard sloop or Ula, a Freedom 32 - your choice each time you reserve sailing time. Both yachts are well equipped, comfortable cruisers. CSC's "Bianca". Tartan 34. CSC's "Ula - Jewel of the Sea". Freedom 32.

  4. Cruising the Chesapeake Bay

    The Chesapeake Bay is a spectacular North American cruising ground that was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago.

  5. Chesapeake Bay Sailing Tours

    Share. Sailing is a quintessential Chesapeake experience, and there are many places and means to serve up its pleasure. Take a spirited cruise under sail and skate across the Bay with the breeze behind you and the sun kissing your face. Book a charter and anchor in a cove to swim and fish for a relaxing fun-filled day, or enjoy a tour aboard a ...

  6. Sailing Cruises in Annapolis, Maryland on the Schooner Woodwind on the

    Welcome Aboard! Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Located in the heart of the Chesapeake Bay, Annapolis is "America's Sailing Capital.". Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the ...

  7. Sail Selina II

    Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour! Book Now. Learn More. From $115.

  8. Bareboat Sailboat Charters

    Bareboat sailboat charters on the Chesapeake Bay, within easy sailing distance of Annapolis, Baltimore, Oxford, St. Michaels. Ph: 410-639-7140 Fax: 410-639-7194 ... 2018 and 2020 Chesapeake Bay Magazine Best of the Bay. Blue Ribbon - Catalina 32 ($1672)* Falken - Catalina 355 ($2059)* Eos - Beneteau 37 ($2176)*

  9. Home

    Sailing on the bay with Chesapeake Windsail Cruises is a beautiful way to enjoy all the splendors of the waters of the Chesapeake Bay, the Cliffs of Calvert or the beautiful environment of the region, all during a wonderful 2 ½ hour cruise on the Chesapeake Bay. Chesapeake Windsail Cruises sails out of the beautiful Rod 'n' Reel Resort located ...

  10. Chesapeake Bay Charters

    Come experience the splendor of the Chesapeake Bay on board a 40 foot sailboat. Private sailing adventures from two hours up to two weeks are available for the whole family. Available services include but are not limited to: Owner/Operators are USCG licensed captains with over 30+ years of combined sailing experience.

  11. Chesapeake Bay Bareboat & Crewed Yacht Charters

    Chesapeake Bay is a vast waterway, 200 miles long draining 64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation.

  12. Homepage Island Chill Yacht Charters

    Call 410-212-4476 for reservations. Island Chill Yacht Charters (ICYC) creates the 'Relaxing Excitement of the Islands' on our Chesapeake Bay sail and powerboat private cruises for Families, Friends and Couples. We're conveniently located in historic Londontowne in Edgewater, close to Washington D.C. & Baltimore, and just 6 miles south of ...

  13. Tips For Sailing The Chesapeake Bay

    Though you're looking for variety then sailing the Chesapeake area is a natural cruising route for discovery, made for simply hopscotching from one shore to the next, with things to see, visit, experience, taste and indulge all of your senses at once. Commonly visited areas include Havre de Grace via the Chesapeake & Delaware Canal built in 1829.

  14. Cruising Sailboats for the Chesapeake Bay

    Cruising Sailboats for the Chesapeake Bay. There's no better way to experience all the Chesapeake has to offer, cruising in a warm breeze with friends and family aboard the Club's J/32's, J/105's, and Beneteau 33. Being a member of the Club makes this dream a reality - and for far less money than ownership, charters or renting a sailboat.

  15. Discover the Upper Chesapeake Bay by Sailboat

    Sometimes Middle and Southern Bay sailors wonder whether the Upper Bay is really sailboat- and sailor-friendly. Our sailing friends who know the area well tell us the Upper Bay has much to offer. The catboat Planet at sunrise on the Upper Chester River, a tributary of the Chesapeake Bay. Sailboat photo courtesy of Craig Ligibel.

  16. Best Sailing Destinations in Chesapeake Bay

    It's no secret that Annapolis, MD is America's Sailing Capital, and it's home to some of the top sailing spots in the country. The Chesapeake is a body of water that stretches 200 miles from the mouth of the Susquehanna River in Havre de Grace to the Virginia twin capes. It varies from 3 miles wide in the north to 25 miles wide in the south.

  17. SpinSheet

    The sailing magazine for sailors by sailors, dedicated to racing, cruising, and daysailing on the Chesapeake Bay.

  18. Best Sailing Destinations Chesapeake Bay

    The best sailing destinations in Chesapeake Bay are Annapolis and St. Michaels along with Norfolk. Other locations worth checking out are Solomons Island and Rock Hall as well as Smith Island. Keep in mind you need to travel the eastern shore of Maryland and Virginia to see all of these locations. In my experience there is not much that ...

  19. Sailing, Learning & Safety

    Church Hill. kt051020304060. Wednesday 13 - 7 AM. Wind. +. -. Looking for one of the best Chesapeake Bay sailing clubs? Northern Chesapeake Cruising Club (NC3) is a sailing club dedicated to cruising, learning & safety.

  20. Southern New Jersey Fishing Report- March 21, 2024

    Cape Cod and Buzzards Bay; Chesapeake Bay; Connecticut; Massachusetts; New Jersey — Northern; New Hampshire, Maine and Vermont; New York - Long Island; New York - Upstate; New Jersey — Southern; Offshore; Rhode Island; Saltwater. 2024 Sportsmen's Shows; 2024 Fishing Tournament Calendar; Stripers & Blues; Bottom Fishing; Kayak ...

  21. The best river cruises and excursions in Moscow

    Moscow river boat cruises — an unforgettable experience with Moskvatrip. A tourist won't embrace Russia wholeheartedly until he goes on a boat trip in Moscow. Enjoy the comfort of our luxury and safe vessels while another Moscow tourist attraction spreads before your eyes. Moskvatrip is your assistant in the choice of Moscow river cruises.

  22. Cruising the Moskva River: A short guide to boat trips in Russia's

    Even though the selection of wines and food is modest, these vessels are still much better than other boats. Sergey Kovalev/Global Look Press. Surprisingly, the luxurious boats are priced rather ...

  23. THE 10 BEST Moscow Boat Rides & Cruises (Updated 2024)

    Explore the scenic and historic attractions of Moscow from the water with the best boat tours and cruises. Enjoy the views of the Kremlin, the Cathedral of Christ the Savior, and the Sparrow Hills on a relaxing or informative boat ride. Or, spice up your trip with some water sports and activities in Moscow. Find out more on Tripadvisor.

  24. 6 ultimate island-hopping itineraries for 2024

    2. Best for families: Croatia. The calm, clear waters of the Adriatic combined with favourable weather conditions in summer provide easy sailing for families and, with more than 1,000 islands ...

  25. Boat enthusiasts flock to see what's docked in San Francisco

    When the Stad Amsterdam, a 19th century style ship with 31 sails, arrived in San Francisco as a stop along its world tour, local sailing enthusiasts went out into the bay to greet it.

  26. Boat tours and river cruises through Moscow: where to take them

    On this map you can see the details of the longest and most classic of the Flotilla Radisson boat tours: 2. Companies that do boat tours on the Moskva River. There are many companies that do cruises on the Moskva River, but the 4 main ones are: Capital River Boat Tour Company (CCK) Mosflot. Flotilla Radisson.

  27. Naples man, Bonita Springs woman die in North Naples boat crash

    John C. Moulder and Judy M. Eaton, both 71, suffered fatal injuries when the 21' Cobia Open Bay boat they were on crashed into mangrove trees.