key west classic yacht charter

Key West Classic Yacht Charter

Photo gallery for key west classic yacht charter.

Overview of Key West Classic Yacht Charter

Popular amenities.

• Pet friendly
• Air conditioning

Explore the area

• Popular Location Stock Island Yacht Club & Marina 5 min drive
• Popular Location Key West Golf Club 5 min drive
• Popular Location Smathers Beach 9 min drive

Rooms & beds

4 bedrooms (sleeps 8), living room, 2 bathrooms, 1 half bathroom, about this property, property manager, house rules, damage and incidentals, important information, you need to know, about the neighborhood.

What's nearby

• Stock Island Yacht Club & Marina - 5 min drive
• Key West Golf Club - 5 min drive
• Smathers Beach - 9 min drive
• Duval Street - 12 min drive
• Clarence S. Higgs Memorial Beach Park - 13 min drive

Getting around

• Key West Intl. Airport (EYW) - 7 min drive

Restaurants

• McDonald's - 5 min drive
• El Siboney Stock Island - 7 min walk
• Hogfish Bar & Grill - 18 min walk
• Yellowfin Bar & Kitchen - 4 min drive
• Roostica Wood-Fire Pizzeria - 16 min walk

Frequently asked questions

Yes, this property has an outdoor pool. Pool types include heated pools.

Yes, this houseboat allows pets (limit 2 total).

Check-in begins at 4:00 PM.

Check-out is at 11:00 AM.

Situated in Key West, this houseboat is within 1 mi (2 km) of Robbie's and Key West Tropical Forest and Botanical Garden. Stock Island Yacht Club & Marina and Lower Keys Medical Center are also within 2 mi (3 km).

Exceptional

10/10 excellent, key west gem, girlfriends weekend in key west, about the host, hosted by kevin werneth.

Why they chose this property

What makes this property unique, more vacation rentals ideas, people also search for, additional information about expedia group.

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

Chillout Lilypad Sail

Key West Daysail

Sunset Sail on When & If

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

When And If is back at beautiful Stock Island Marina!

Check Out Our Ship's Store!

Wreckers' Race Season Is Back!

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

Friends of SSKW

Legal & safety.

Expedia Rewards is now One Key™

Key west classic yacht charter, photo gallery for key west classic yacht charter.

Overview of Key West Classic Yacht Charter

Exceptional, popular amenities.

• Pet friendly
• Outdoor Space

Explore the area

• Popular Location Stock Island Yacht Club & Marina 5 min drive
• Popular Location Key West Golf Club 5 min drive
• Popular Location Smathers Beach 9 min drive

Space details

About this property, entire place, property manager, property amenities.

• Beach towels
• Communal pool
• Heated pool
• Outdoor pool

Parking and transportation

• Parking on site
• Coffee/tea maker
• Cookware, dishware, and utensils
• Paper towels
• Refrigerator
• Dining table
• Bedsheets provided
• 3 bathrooms
• Bathtub or shower
• Toilet paper
• Towels provided

Living spaces

• Living room

Entertainment

Outdoor areas.

• Barbecue grill
• Outdoor furniture
• Washing machine

Work spaces

• Air conditioning
• 2 pets total

Suitability/Accessibility

• Designated smoking areas

Services and conveniences

• Iron/ironing board

Things to do

• Boat on site
• Heated pool on site

Safety features

• Carbon monoxide detector
• Fire extinguisher
• First aid kit
• Smoke detector

Similar properties

Oceans Edge Key West Resort, Hotel & Marina

The Laureate Key West

Margaritaville Beach House Key West

Courtyard by Marriott Key West Waterfront

Special check-in instructions, children and extra beds, important information, you need to know, about the neighborhood, what's nearby.

• Stock Island Yacht Club & Marina - 5 min drive
• Key West Golf Club - 5 min drive
• Smathers Beach - 9 min drive
• Duval Street - 12 min drive
• Clarence S. Higgs Memorial Beach Park - 13 min drive

Getting around

• Key West Intl. Airport (EYW) - 7 min drive

Restaurants

• McDonald's - 5 min drive
• El Siboney Stock Island - 7 min walk
• Hogfish Bar & Grill - 18 min walk
• Yellowfin Bar & Kitchen - 4 min drive
• Roostica Wood-Fire Pizzeria - 16 min walk

Frequently asked questions

Yes, this property has an outdoor pool. Pool types include heated pools.

Yes, this houseboat allows pets (limit 2 total).

Check-in begins at 4:00 PM.

Check-out is at 11:00 AM.

Situated in Key West, this houseboat is within 1 mi (2 km) of Robbie's and Key West Tropical Forest and Botanical Garden. Stock Island Yacht Club & Marina and Lower Keys Medical Center are also within 2 mi (3 km).

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. More information Opens in a new window

10/10 Excellent

Kelly r., san antonio, key west gem, renee p., rochester hills, girlfriends weekend in key west, expedia's latest trends, additional information about expedia group.

Yachting in Key West, FL

Located at Florida's southern tip, Key West captivates with azure seas, vibrant coral reefs, and a relaxed vibe. Experience the island's allure and enjoy luxury yachting in Key West, FL. Perfect for leisurely cruises or thrilling adventures, Key West is ideal for sun-filled coastal experiences. Discover its beauty from the deck of your private yacht.

52' Viking Princess

80' FF Pendleton

75' Luxe Catamaran

Why charter a yacht in key west, fl, traverse hidden treasures with key west luxury yacht charters, boat rental in key west, .css-1uazooj{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;width:100%;outline:2px solid transparent;outline-offset:2px;transition-property:var(--chakra-transition-property-common);transition-duration:var(--chakra-transition-duration-normal);font-size:1rem;-webkit-padding-start:var(--chakra-space-4);padding-inline-start:var(--chakra-space-4);-webkit-padding-end:var(--chakra-space-4);padding-inline-end:var(--chakra-space-4);padding-top:var(--chakra-space-2);padding-bottom:var(--chakra-space-2);padding:10px 16px;}.css-1uazooj:focus-visible,.css-1uazooj[data-focus-visible]{box-shadow:var(--chakra-shadows-outline);}.css-1uazooj:hover,.css-1uazooj[data-hover]{background:var(--chakra-colors-blackalpha-50);}.css-1uazooj[disabled],.css-1uazooj[aria-disabled=true],.css-1uazooj[data-disabled]{opacity:0.4;cursor:not-allowed;} .css-1pkhz46{font-size:var(--chakra-fontsizes-sm);font-weight:600;-webkit-flex:1;-ms-flex:1;flex:1;text-align:left;} how do i book a yacht on yachtlife .css-g5ledl{width:1em;height:1em;display:inline-block;line-height:1em;-webkit-flex-shrink:0;-ms-flex-negative:0;flex-shrink:0;color:currentcolor;vertical-align:middle;font-size:8px;}, when is my payment collected is it refundable.

Once you confirm your reservation, your broker will process your payment.

• If you are booking for a single day and your reservation is confirmed more than 7 days in advance, a deposit of either $1,000 USD or 50% of the total cost of the reservation (whichever is greater) is processed immediately in order to hold the yacht. Once your embarkation date is 7 days away, the remainder of the amount due is processed.
• If you are booking for a single day and your reservation is made 7 days or less in advance, the total price of your reservation is processed immediately.
• If you are booking for a multi-day charter and your reservation is confirmed more than 30 days in advance, a deposit of 50% of the cost of the yacht is processed immediately in order to hold the yacht. Once your embarkation date is 30 days away, the other 50% is collected for the price of the yacht, plus the APA, plus the taxes due.

Terms of refunds are dictated by the Charter Agreement. Generally, once a payment is collected, it is non-refundable. In certain circumstances, as dictated by the Charter Agreement, credits can be provided so you will be able to enjoy your yacht charter at a future date that is convenient for you.

Why is there a 3% credit card convenience charge?

Are my payment details saved on the app, what if your servers get hacked is my payment information really safe.

 Key West & Marathon, Florida

We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.

Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing.  We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys.  Just looking for a day charter?  Look no further.  We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.  

Florida Keys Yacht Charters

EXPERIENCE LEVEL

Key West is a Florida staple and the southernmost point of the continental USA, famous for its pastel island homes, beautiful reefs, and lively nightlife. Being home to the United States’ only living coral barrier reef makes this a desirable snorkeling spot for all. This part of the keys is closer to Cuba than Miami making it a tropical paradise with the perfect mix of history, natural splendor, and unique architecture.

Take a walk down palm lined streets and explore the historical homes of Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, and Jimmy Buffett. The Florida Keys possess everything necessary to have a dream vacation.

Please note: This base is seasonally closed September 7 – 21. This base is also closed July 4th, November 25th, and December 25th.

You must be qualified to sail in this destination. Please submit a Captain’s Resume and a First Mate Resume before booking this destination. Your Vacation Planner will request these forms upon booking your yacht.

• White sand beaches
• Charming local stores and boutiques
• Variety of museums

Key West Highlights

Island bars, quiet beaches, beautiful scenery, and coral reefs make this stretch of The Florida Keys an unforgettable place to sail. Expect crystal clear waters while cruising along picturesque coastlines and soak in the tropical vibes of the local beaches. Each stop along the way has its own appeal but make sure not to miss out on the vibrant streets of Key West and the nightlife that goes along with it.

Key West – 7 Days Itinerary

Sailing in The Florida Keys is all about sightseeing, unforgettable sunsets, and clear blue waters full of wildlife. This location is home to the third largest barrier reef in the world meaning there are miles of protected cruising grounds behind natural reefs that house a lavishness of colorful fish and coral. 70 miles west of Key West lies the remote Dry Tortugas National Park. The park is home to world famous Fort Jefferson and is known for dazzling blue waters, the healthiest coral reefs in the Florida Keys and prolific bird life that frequent the area. You will receive a comprehensive boat checkout from our expert staff at the base including a chart briefing and boat walk through. They will give you all the support you need to make this trip unforgettable. Throughout your vacation you will find that the Keys have everything you could need just a short trip away no matter where you are. From provisioning to local restaurants or a night out, there is a stop along the way for an onshore adventure at every turn. Enjoy everything these majestic islands have to offer on your own time when you take a bareboat charter.

Please note: Key West Florida is a partner base. No credit certificates or discounts, e.g. Captain’s Rewards or Special Offers, apply in this destination. You must also be qualified to sail in this destination.

Key West to Bahia Honda – 5 Day Itinerary

Award winning yacht.

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What Guests are Saying

Base Partner in Key West was outstanding. John Carlton Key West

The boat was in great condition. Process was easy. Mark Wulkan Key West

The group we worked with in Key West was great and very responsive and sailing in the Keys was a great time. Boat was a little dated and seemed to be in need some maintenance, which I believe our boat was a leased owner boat and not a Moorings owned boat. We might be a little biased as our first Moorings experience was in BVI and that was just a different level. The crew in Key West though was great and appreciated their help. Nat Killpatrick Key West

We had an excellent time. The staff was extremely helpful and the boat was immaculate. Thanks to everyone who made our vacation flawless!!! Dan Keeley Key West

We had a fabulous six day trip on a band new Beneteau 410 sailing from Key West to Marathon Key. Boat was superb and John, Emily and Kim were very helpful. Chartering is the only way to go. See you next year! David Simson Key West

Excellent customer service from start to finish. Lindsey assisted in accommodating all of our requests. Kimber was amazing from start to finish. Her passion for her profession was omnipresent. Stacey Rogers Key West

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How to rent a yacht in key west, find the perfect boat.

Enter your desired location and date to explore our fleet of yachts.

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Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

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Top yacht rentals reviews in Key West, FL

Duet - 2023...

We had a group of 12 people (plus 2 captains) and fit very comfortably on the top/main part of the boat. It was...

48' SAILING...

Both Brian and Patrick operated the boat and were outstanding hosts to our full family.

All of us were very...

Luxury 45’ Sea...

Boatsetters works like a charm. Great communicaton from the booking agent Tim in Key West thru to the boat owner and...

Florida Keys...

Thanks Capt. John! Your boat was a beauty and we appreciate all the individual attention you and Tina provided me...

Captain Jason and first mate Kristy are the best!

Luxury 51' Power...

The boat was beautiful and spacious. The weather was not ideal but our captain Justin and his crewmate Tyler made the...

Fantastic day on BellaMaggio! Rented for a family day in Key West with 5 adults and 4 kids (ages 1-12). Everyone was...

Luxurious Private...

It was an amazing experience! We spent about 4 hrs on the yacht, sailing through Atlantic Ocean and Gulf of Mexico,...

The experience. The communication. The boat. The crew. All top notch from beginning to end. Thank you Brian and...

The Happy Prince...

Visitors from the UK. Always wanted to explore the sea around Key West in style and that we did! We had a the best...

Yacht Rentals in Key West, FL

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Experience the yacht lifestyle on the Mia in beautiful Key West, FL.

The Mia Services

All cruises are BYOB for alcoholic beverages, food or snacks. A chef can be provided if desired to prepare your special meal, additional info and cost will be provided upon request. Full galley, grill, coolers, ice, bottled water, sodas, glasses and place settings, utensils, blender, and crew is provided. ​Sunset times vary throughout the year, for times available click please send a request for your desired dates.

All cruises and routes are subject to change due to docking, weather or current conditions, USCG restrictions or Captains' discretion.

Take A Video Tour

The Mia Yacht in Key West was a wonderful experience for our family, beautiful memories were made. Top notch service, would highly recommend to anyone. A trip out to Boca Grande Island is a must if you’re visiting...The atmosphere of Stock Island Marina was amazing, lots of amenities. Truly a wonderful place to gather on any occasion. We definitely will be returning.

Best Day Ever!! Owner Mike and Captain Ryan and crew are the pinnacle of service and professionalism. If you like 1st class service and beautiful accommodations, Mia is the boat for you.

Latest News

Explore Your Rental

Custom Private Charters

Sunset Cruise In Style

Key West Island Excursions

Only Hinkley in Key West

Handcrafted Teak Cockpit

Comfortable Seating For 6

Cruising key west and the lower keys in class.

Courage Charters offers the very best in Key West leisure and sea limousine style tours.

Our private charters are built around comfort. The shallow draft and smooth ride make for a peaceful cruise through the backcountry islands of the Lower Keys. This semi-custom built 36 foot Hinckley Classic Picnic Boat is class all the way. Courage features a spacious deck, a handcrafted teak interior, multiple seating options, and a below deck bathroom. Complimentary ice and bottled water are provided with ample cooler space to accommodate any refreshments you would like to bring. To complete your experience, ask about adding a private picnic at sea.

Truly a limousine on the water. 

Secluded Island Excursion

Intimate sunset cruise, historic seaport tour, dolphin watching, on board picnics available.

Call (314) 795–5534 to Book

Kick Back Aboard This 36’ Hinckley Classic Picnic Boat

Custom key west island excursion.

4 Hour Private Charter

For a truly unforgettable experience, chart your own course aboard this beautiful Hinckley power boat and explore the pristine waters of Key West and the Lower Keys. Courage accommodates up to six passengers plus captain. Perfect for a relaxed special occasion, or intimate sunset cruise. Start your day off splashing around in the shallows, searching for dolphin, or wade in the ankle-deep waters just a short cruise from shore.

Circumnavigate Key West

Explore hidden sand bars, cozy up to the setting sun, special events & ceremonies, romantic getaways.

We will customize your tour to suit your interests. Cruise by the southern Key West shore on the Atlantic Ocean.  Enjoy a leisurely tour through the Historic Seaport or wind through the backcountry to anchor out at a remote island.  If you chose, enjoy an onboard picnic or a hand-rolled Key West local Rodriguez cigar. You decide how much time we spend where.

SEE FULL GALLERY

Hand rolled Key West cigars available on board.

From the blog.

Learn more about our boat tours, fun stories and interesting facts about the Florida Keys in Our Blog .

Guests Reviews

Read more reviews or leave one of your own on Facebook .

I had a wonderful time on my sunset cruise with captain George. Excellent customer service and expert navigation made for a great experience. He took lots of pictures, so I could just focus on having fun

Grace Boston – FL

Literally just returned from a charter. Captain George was phenomenal!! His boat is breathtaking 5 + stars. Such beauty and peace Highly recommend. An experience you should not miss.

Evelyn Bowlby – NJ

Captain George and his amazing Hinckley boat is the very best Key West has to offer, I am delighted always with this amazing trip and the kind entertaining Captain has to offer. Private island no problem, dolphins no problem the perfect picnic no problem and all done in perfect style! Highly recommended! First Class!

Laurie Jane Henderson

A day on Courage with Captain George was the best day! A beautiful boat and a captain who clearly loves to give his guests a once in a lifetime experience! I can only hope to get a chance to experience this perfect day again!!

Annie Dickerson – MO

This was one of the best days of our entire life!! Cruising on a first-class Hinckley boat for an entire afternoon was a dream come true! We had lots of fun looking for shells on a beautiful island as well. Captain George was the best, so nice and friendly!! What a great experience! We’d do it again tomorrow if we could!

Mark Cioffi – NY

Contact Courage Charters

Contact Captain George

Owner / Operator

(314) 795 – 5534

Key West Harbor 6000 Peninsular Ave. Key West, FL 33040

Home | Key West Excursion | Gallery | Call (314) 795-5534 to Book Copyright 2019 Courage Charters | All Rights Reserved Site By AP Design Services

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Welcome to the Best Private Yacht Charter in Key West

Boating is a way of life in southern Florida. When you’re visiting on vacation, you can elevate your experience by spending time on the water. At After Hours, we provide a selection of boat tours with private boat charters in Key West to give you the boating experience you need to enjoy true vacation bliss during your time in the Keys. Whether you’ve been searching for the best sunset cruise or want to take a day trip to enjoy fun in the sun with the opportunity to see dolphins and other marine life, we have the options you need for the ultimate experience.

Enjoy Our Specially Designed Boat Tours

Whether you’re interested in a sunset cruise to enjoy the tranquility of a beautiful sunset in the Keys or want to take a day trip that introduces you to local wildlife while you take in the sights from a unique perspective, our boat tours will give you the ultimate experience. Our experienced captains know the best places to take you to walk on pristine private beaches, swim in crystal clear waters, or even snorkel with sea turtles. We work hard to give you and your group the most amazing experience possible. We even include customized catering while you’re onboard with us.

Get a Private Boating Experience

When you book a private yacht charter with us, we will pamper you with the best experience you could dream of. We’ll help you leave the real world and the crowds behind, so you feel like you’re the only person on the planet. A private boat charter is ideal for heading out for some solitude or sharing an intimate experience with that special someone, your family, or a close group of friends. We customize each experience based on your preferences, so you’ll have the time of your life!

If you’re looking to make your Key West vacation extraordinary, we have the solution. After Hours is a private yacht charter that can take you and your guests to vacation bliss.

Why Choose After Hours?

Key West Yacht Charter on After Hours

Welcome aboard After Hours

You work hard. Your vacation days are precious. Why spend them in a crowd?

Your perfect day in paradise is custom-made to give you the pampering you need. This is your chance to break away from the masses and go beyond the ordinary.

On A Private Yacht

You left your hectic life behind to take a vacation. Why spend it in a crowd? Let us pamper you with a day, evening, or extended cruise in private luxury. Onboard After Hours, you’ll enjoy food and drink tailored to your tastes as you leave the real world (and its crowds) behind.

With Your Special Guests

Imagine hosting your closest friends and family for an amazing outing that they’ll remember for years. Or show your important clients or colleagues how much they are valued with a one-of-a-kind experience. Or even pop the question in a way that almost guarantees a “YES!” with a romantic proposal trip. Life’s big moments deserve special treatment. 

Your Trip, Your Way

Sunset cruise.

Key West sunsets are legendary. But, imagine a private sunset cruise during your visit to Key West. Sunsets are one of the most romantic experiences in Key West. Get away from the crowds and make it special on your own private charter.

You’ll never forget your After Hours day trip in Key West, FL. Cruise to a secluded island with crystal clear waters. We can be your escape to adventures based on what you want. Walk on a secluded beach? We know the best ones. Snorkle with sea turtles? Let us introduce you.

Key West Events

There’s always a festival or holiday being celebrated in Key West. What better way to participate than aboard After Hours private yacht charter. Sunset cruises or day trips, you’ll never forget this private yacht charter in Key West.

Yacht Charter Miami To Key West: Ultimate Guide

Embarking on a yacht charter from Miami to Key West is an adventure we’ve explored inside and out. With our background in the private jet business, we’ve got a knack for luxury travel that translates seamlessly to the sea. This journey is more than just a trip; it’s a curated experience that promises unparalleled views, exclusive snorkeling spots, and sunsets that you have to see to believe.

We’ve poured our expertise and thorough research into crafting an article that not only guides you through this exquisite voyage but ensures you’re getting the most out of every nautical mile. Whether you’re drawn to the allure of the open ocean or the charm of the Florida Keys, our insights will steer you towards an unforgettable journey. Keep reading to discover the best yacht charter options from Miami to Key West, tailored just for you.

Key Takeaways

Table of Contents

• Personalized Experience: A yacht charter from Miami to Key West is synonymous with luxury, offering a customizable journey where everything from the travel route to on-board amenities can be tailored to your preferences, ensuring a unique and exclusive adventure.
• Unparalleled Access: Opting for a yacht charter allows exclusive access to secluded spots along the Floridian coast, including hidden gems like secret snorkeling locations and private beaches that aren’t accessible to larger vessels, making for a truly unique exploration.
• Spectacular Natural Encounters: The journey promises encounters with breathtaking scenery and wildlife, offering opportunities to connect with nature, from dolphins playfully trailing the yacht to snorkeling in pristine coral reefs rich with marine life.
• Top-Notch Comfort and Amenities: Modern yachts are equipped with luxurious amenities ranging from spacious decks for sunbathing, advanced entertainment systems, to comfortable cabins ensuring a blend of adventure and pampering throughout the voyage.
• Must-Visit Destinations in Key West: Once in Key West, explore must-see attractions like the historic Fort Jefferson, vibrant Duval Street, the enchanting Key West Butterfly and Nature Conservatory, and the iconic sunset celebrations at Mallory Square.
• Planning for Perfection: For a memorable yacht charter, choosing the right yacht, planning the itinerary with key highlights, ensuring safety, and personalizing the experience according to one’s taste are crucial elements that contribute to the success and enjoyment of the trip.

Benefits of Yacht Charter from Miami to Key West

Embarking on a yacht charter from Miami to Key West isn’t just about traveling; it’s about experiencing unparalleled luxury and freedom on the seas. Let’s explore why this journey is a must-do for those seeking adventure and relaxation in equal measure.

First off, Customization is key. We’re not just talking about the route, but the entire experience. Whether it’s the culinary preferences, leisure activities, or the pace at which we travel, everything can be tailored to suit our desires. It’s like having a floating five-star hotel that goes wherever we want, whenever we want.

Exclusivity comes hand in hand with a yacht charter. We get to explore hidden gems along the Floridian coast that are inaccessible to larger vessels. From secret snorkeling spots bursting with marine life to secluded beaches where we can unwind without a care in the world, these moments make our journey truly unique.

The scenery and wildlife we encounter are nothing short of breathtaking. Picture gliding through crystal-clear waters, with dolphins playfully chasing the wake of our yacht. Or, imagine anchoring at a pristine coral reef for an impromptu snorkeling session. This voyage offers endless opportunities to connect with nature in ways we’ve never imagined.

Lastly, comfort and amenities on board are top-notch. Think spacious decks for sunbathing, state-of-the-art entertainment systems for evening movie sessions, and luxurious cabins that guarantee a good night’s sleep after a day full of adventure. It’s the ultimate blend of adventure and pampering.

Choosing the Right Yacht for Your Charter

When planning our yacht charter from Miami to Key West, one of the most critical decisions we’ll make is selecting the right yacht. It’s not just about the length or the price; it’s about matching our needs, our dream experience, and the yacht’s capabilities. Here’s how we can break it down to make sure we’re on the right path.

Yacht Sizes

First, we need to consider size and type. Are we looking for an intimate experience with a close group of friends or a larger gathering with family? Yachts come in various sizes, from sleek and sporty models perfect for couples or small groups to larger vessels that can accommodate parties of 12 or more. The type of yacht—sailing yacht, motor yacht, or catamaran—also affects our experience. Sailing yachts offer a more classic and hands-on sailing adventure, while motor yachts provide speed and luxury. Catamarans, known for their stability and space, are ideal for those who may be prone to seasickness or want the extra room.

Next, let’s talk amenities. Modern yachts come equipped with a variety of facilities to enhance our journey. From on-board Jacuzzis and state-of-the-art entertainment systems to water toys like paddleboards, kayaks, and snorkeling gear, these amenities can significantly impact our enjoyment. When choosing our yacht, we’ll want to think about which features are most important to us.

Lastly, crew and service. The expertise and hospitality of the crew can make or break our charter experience. A knowledgeable and friendly crew not only ensures our safety but also caters to our every need, from navigating the best routes to preparing gourmet meals. Reading up on reviews and seeking recommendations are great ways to ensure we select a charter company that prides itself on exceptional service.

By considering these factors—size and type, amenities, and crew and service—we’re on our way to selecting the perfect yacht for our Miami to Key West adventure.

Planning Your Itinerary Along the Way

When embarking on a yacht charter from Miami to Key West, we’ve got a few insider tips to help you plan the ultimate itinerary. This journey offers a mix of sapphire waters, vibrant coral reefs, and unforgettable stops that are sure to make your trip extraordinary.

First off, don’t miss the chance to glide through Hawks Channel where the playful dolphins and graceful turtles are a common sight. It’s moments like these that truly enrich your adventure. Another spot we highly recommend is the breathtaking Looe Key Reef. Here, the dazzling array of fish and sea creatures will leave you in awe, making it a top pick for anyone who loves snorkeling or diving.

For those seeking a dash of luxury, Little Palm Island Resort offers an exclusive escape that’s just off the beaten path. Imagine anchoring nearby and reveling in the tranquility of this private paradise. It’s the perfect way to add a touch of elegance to your journey.

As you sail towards Duck Key, take a detour to Sombrero Key for some of the best snorkeling in the area. The water clarity and marine life here are unparalleled. Lastly, rounding off your trip at Bahia Honda provides the chance to experience iconic Florida Keys scenery, from palm-lined beaches to crystal-clear waters and stunning sunsets.

Our proposed pit stops:

• Hawks Channel
• Looe Key Reef
• Little Palm Island Resort
• Sombrero Key
• Bahia Honda

Each of these locations offers something unique, from thrilling wildlife encounters to serene beachside sunsets. We’ve crafted this journey to blend adventure, relaxation, and luxury, ensuring that every moment aboard is nothing short of magical. Remember, it’s all about creating a voyage that speaks to your spirit of exploration and relaxation. So, take our suggestions, tailor them to your desires, and set sail for an unforgettable experience on the waters from Miami to Key West.

Exploring Key West: Must-See Attractions and Activities

When embarking on a yacht charter from Miami to Key West, the allure of the open sea is undeniable. However, arriving in Key West unveils a new adventure that’s as vibrant and colorful as the reef below the waves. We’re here to guide you through the must-see attractions and activities that make Key West a quintessential stop on your seafaring journey.

First up on our list is the historic Fort Jefferson in the Dry Tortugas. Just a day’s sail from Key West, this monumental fortress offers guided tours that reveal the rich history of the area. It’s not just a lesson in the past; the surrounding waters boast some of the most pristine coral reefs in North America, making it a paradise for snorkelers and divers.

As we navigate back to the heart of Key West, we can’t skip the famous Duval Street . It’s where the spirit of Key West comes alive with its eclectic mix of restaurants, bars, art galleries, and shops. Whether you’re in the mood for a seafood feast or just want to soak up the local culture with a cold drink in hand, Duval Street caters to all tastes.

For those of us who are wildlife enthusiasts, a visit to the Key West Butterfly and Nature Conservatory is a must. It’s a magical place where hundreds of butterflies flit through an indoor tropical paradise, creating a serene experience unlike any other. Plus, the conservatory’s learning center provides fascinating insights into the lifecycle of these vibrant creatures.

And of course, no trip to Key West would be complete without watching a sunset at Mallory Square . It’s a daily ritual where tourists and locals alike gather to witness the sun dipping below the horizon, painting the sky in breathtaking hues of orange and pink. Street performers, musicians, and food vendors add to the festive atmosphere, making it a celebration of nature’s beauty and human creativity alike.

Each of these destinations offers a glimpse into the diverse tapestry that is Key West. Whether we’re delving into historical wonders, indulging in the local nightlife, connecting with nature, or simply enjoying a sunset, Key West has something special for every traveler.

Tips for a Memorable Yacht Charter Experience

Embarking on a yacht charter from Miami to Key West is an adventure we all dream of, but it’s the small details that turn a trip into an unforgettable experience. Here, we’ll share some insider tips to ensure your journey on the water is nothing short of spectacular.

First off, choosing the right yacht is crucial. It’s not just about size or luxury, but also about how well it fits your group’s needs. Consider comfort, amenities, and the kind of experience you’re aiming for. Whether it’s lounging on deck under the sun or having high-tech equipment for water sports, make sure the yacht meets your wishlist.

Next up, let’s talk about planning your itinerary . While spontaneity has its charms, a bit of planning goes a long way. Key West is brimming with sites and activities, and you’ll want to hit the highlights without feeling rushed. Allocate time for Fort Jefferson in the Dry Tortugas, an afternoon stroll down Duval Street, and yes, a sunset at Mallory Square is a must. But also leave room in your schedule for those unexpected gems you discover along the way.

Safety is non-negotiable, so brush up on maritime safety procedures before you set sail. Familiarize yourself with the yacht’s safety equipment and make sure everyone on board knows basic safety practices. It might not be the most exciting part of your trip prep, but it’s definitely one of the most important.

Personalizing your experience is what sets yacht charters apart from other types of travel. Talk to your charter company about arranging special activities or experiences, like a private tour of Key West’s hidden spots or a gourmet meal prepared on board by a chef. It’s these touches that create memories lasting a lifetime.

Remember, a yacht charter is more than just a trip—it’s an opportunity to explore, relax, and create lasting bonds. With the right preparation and a spirit of adventure, we’re sure your Miami to Key West journey will be everything you’ve dreamed of and more.

Embarking on a yacht charter from Miami to Key West offers a unique blend of luxury, adventure, and personalization that’s hard to find elsewhere. We’ve shared how selecting the right yacht and tailoring the itinerary can elevate your experience, ensuring every moment is as breathtaking as the views. By focusing on safety and customization, we’re confident your journey will be unforgettable. Remember, it’s not just about the destination but the memories you create along the way. Let’s set sail on an extraordinary adventure that’s tailored just for you.

Frequently Asked Questions

Can i charter a yacht from miami to key west.

Yes, you can charter a yacht from Miami to Key West. This offers a personalized and exclusive experience, allowing you to enjoy breathtaking scenery and wildlife along the way. Customization options are also available to tailor the journey to your preferences.

How much does a yacht charter from Miami to Key West cost?

The cost of a yacht charter from Miami to Key West varies based on the yacht’s size, amenities, and the duration of the charter. Prices start from a few thousand dollars for a day trip and can increase significantly for luxurious or longer charters.

What are the benefits of choosing a yacht charter over other forms of travel?

Yacht charters offer unparalleled customization, exclusivity, and direct access to breathtaking natural scenery and wildlife. They also provide top-notch comfort and amenities onboard, making the journey as enjoyable as the destination.

How do I choose the right yacht for my charter?

Consider the size, type, amenities, and budget when choosing a yacht. It’s important to select a yacht that can comfortably accommodate your group and meet your specific needs for the trip.

What should I include in my itinerary when planning a yacht charter from Miami to Key West?

Your itinerary should include stops at scenic spots, wildlife viewing opportunities, and any specific locations you wish to visit. Planning for relaxation time and activities on board is also important to enhance your experience.

How can I ensure safety during my yacht charter?

Ensure safety by choosing a reputable charter company with experienced crew members. Always follow safety instructions provided onboard, and check that the yacht is equipped with updated safety equipment.

How can I personalize my yacht charter experience?

Personalize your yacht charter experience by discussing your preferences with the charter company beforehand. This could include meal plans, entertainment options, and specific routes or destinations you wish to explore.

Get an extra discount by calling us now and using promo code “VIP-ACCESS”.

Speak to our yacht specialist and see why we have the highest ratings in the industry!

April 27, 2015 by [email protected]

Classic Harbor Line Key West Crew is the operating the Schooner America 2.0 out of the Key West Bight. Operating sunset sails and day sails on Key West waters since 2008, Classic Harbor Line specializes in bringing beautiful, classic-style yacht to the Key West waterways and creating special and memorable excursions. 

Our Crew, including all captains, mates, chefs, and on-land representatives at Classic Harbor Line, is what make the experience on our beautiful yacht truly magical. We have maintained a consistent history of not only operating with a professional staff, but also with warm and inviting hosts. You will, without a doubt, get a fantastic glimpse of the green flash on your Key West Sunset Cruise and find this yacht beautiful and comfortable, but what will surprise you and stay with you when you leave is the warm and special treatment you receive from our extraordinary team.

Comments Off on Our Crew

Our Captains

All of our captains are Coast Guard certified. The Schooner captains all have a minimum 100-ton license and a sailing endorsement. Our captains are also trained in first aid and CPR and are registered in an ongoing drug-testing program. Perhaps of equal importance, we require that our captains have an appreciation for quality service and are extremely charming hosts.

Mates on the Schooner America 2.0 undergo extensive safety and marine training. Many of the schooner mates also have extensive sailing, racing and/or teaching experience on smaller sail vessels.

Our mates are widely remembered for their remarkable hospitality and personality which is consistently praised in our customer reviews. They love talking with our guests, sharing information on the great island of Key West, and conveying their love for our classic-style yachts and the addictive mystique of being out on the water. If you are interested in joining our crew, please send a cover letter and resume to: [email protected]

Our Land Ambassadors

There are a number of behind-the-scenes crew members at Classic Harbor Line Key West. They are the team who answers the phones, plans your event, greets you on the pier and is happy to tell everyone about the cool cruises and sails that we offer.

Everyone who buys a ticket for trips gets to meet a Land Ambassador at check-in. They are full of information and they are the most hospitable people you will ever meet! Ask them for recommendations on dinner after or before a sail or a suggestion on a future excursion.

Employment with Classic Harbor Line

If you are interested in employment with Classic Harbor Line Key West, we want to hear from you! We are always looking for experienced captains and mates with a strong background in hospitality and/or marine maintenance. Please feel free to forward a letter and resume to [email protected] .

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