yacht charter in key west

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.

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.

305-900-7263

HAVANA FLEET

Luxury charters, charter your dream yacht and experience the adventure of a lifetime.

Havana Fleet Key West Luxury Yacht Charters offers guests an unforgettable experience aboard our fleet of luxury charter boats. Our experienced Captain and Crew will treat you and up to eleven guests like true celebrities, ensuring that you have a once-in-a-lifetime experience. At Havana Fleet, no two trips are alike and every charter can be custom-tailored to your needs & specifications. Custom charter options are endless, so whether you want a relaxing 2 1/2-hour Sunset Cruise or a multi-day adventure 90 miles into the Gulf of Mexico, we have you covered. From your secluded anchorage, you can enjoy stunning sunsets and star-lit skies. Plus, with access to world-class snorkeling and beaches on Loggerhead Key, you can explore at your leisure. Water toys, sport fishing, and personal chef options are also available for your enjoyment. Learn more about our fleet of boats and our luxury charters below. 

CHARTER ACTIVITES

Book your adventure.

The Havana Fleet offers a wide selection of activities for everyone. Some of the most popular are snorkeling, fishing, island adventures, sandbar excursions, and sunset cruises. Contact us to plan your luxury charter today.

PRICING & INFO

Havana Fleet offers a wide variety of charter options. We have three different luxury charter boats that offer private luxury charters starting at the price listed below.

2.5 HR CHARTER

Elegant Sunset or Morning Cruises onboard our 36′ Hinckley Picnic Boat, Dolphin Watching, 2 1/2, 4, 6, and 8-hour Custom Island Tour Packages which can include catered onboard or beach picnics. Water toys are available.

2.5 HOUR CHARTER

Your custom charter options are endless! From a relaxing 2 1/2 hour Sunset Cruise 4,6 or 8 hour Island excursion up to a Multi-day and Night adventure 90 miles into the Gulf of Mexico. Explore Fort Jefferson and experience the world-class snorkeling and beaches of Loggerhead Key at your leisure.  

Sunset & Brunch 2.5Hr Cruises are available. Dry Tortugas day trips. Tour Fort Jefferson and snorkel Loggerhead Key. 4, 6, and 8-hour and Multi-day High-end Fishing Charters. Thrilling Sunset Cruises. Express Island Tours and Adventures. Water toys are available.

PRIVATE CHARTERS

Experience the ultimate adventure with Havana Fleet in Key West, Florida. Our luxury charter boats cater to your desires, offering custom trips with tailored destinations and activities for groups of up to 12 people. From half-day to multi-day charters, every detail is addressed by our attentive captain and crew. Explore Fort Jefferson & The Dry Tortugas on our exclusive day trips. Let's plan the charter of your dreams with Havana Fleet today!

3 vessels to choose from

Our fleet of luxury charter yachts offers something for everyone. With options for a group of up to 6 or up to 12 guests on our private luxury charters.

Amazing Destinations

Our fleet offers the chance to experience remote destinations like the Dry Tortugas. Experience untouched locations just for the day or on a multi-day excursion aboard our luxury yacht.

Professional Crew

Our dedicated captains and crew are first and foremost committed to the safety of you and your guests while ensuring an unforgettable experience.

Multi Day Trips

Our fleet offers guests the chance to stay aboard and really get a feel for the yacht life. Our crew can plan an amazing itinerary for your guests. Chefs and catering are available to suit your needs.

2.5 HOUr CHARTER

Looking for adventure but don’t have all day? A 2 1/2 Hour Charter will get you on the water and offer enough time to explore some of the local sights or take in a sunset. Activities include island adventures, or sunset cruises.

4 HOUR CHARTER

Spend an afternoon or morning exploring the uninhabited offshore islands and sandbars. Have time to relax on the water and experience more. Activities include island adventures, sandbars excursions, and sunset cruises.

6 HOUR CHARTER

Spend the day on the water enjoying everything our fleet has to offer. Create a custom itinerary that includes a number of destinations and activities of your choice like a sunset cruise and our sandbar excursion or other combinations.

8 HOUR CHARTER

Have the whole day to see what is out there. A full-day charter opens the door to many remote destinations. Our charter boats can comfortably accommodate up to 6 guests on a day trip to Fort Jefferson & The Dry Tortugas.

START THE JOURNEY

Plan your trip.

Let's plan a custom Key West Charter together. Use the contact form below to tell us a little more about your trip.

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.

Keys YachtCharter.com  Key  West  Luxury  Yacht  Charters

Key West      Lower Keys      Back Country     Sand Bars       Atlantic      Fishing      Sunsets

Schedule your next fishing trip with us... Mahi, Tuna, Wahoo...

Don't miss our sunsets! The Florida Keys are known for some of the BEST sunsets

The best place to spend your weekends with or without the Kids!!!

Need a Boat?

Contact us for  availability

© 2021 Owned and Operated by Key West Luxury Yacht Charters, LLC. DBA - Keysyachtcharter.com. All rights reserved

Charter.com

Want a Slide Boat?

Available for charter, 2020 - nauticstar 231 hybrid, length - 22' 9" / 6.93 m , beam - 102" / 2.59 m, maximum hp w/seastar steering -  250 hp / 186 kw, transom height - twins  - 25", approximate draft -  13" / 0.33 m, deadrise @ transom - 13° , deadrise @ entry - 35°   , approximate weight   - 2650 lb / 1202 kg, *fuel capacity   - 74 gal / 280 l , in-console livewell/baitwell  -  15 gal / 57 l, aft livewell (port side)  - 27 gal / 102 l , aft fish box   - 50 gal / 189 l   , persons/total weight   - 10/1350 lb / 612 kg, max weight capacity   - 1854 lb / 841 kg, for sale profitable opportunity  the exquisite 1991 46 pilothouse charter boat.

Bareboat Charter Key West

by "Charter Booker" | Dec 19, 2017 | Yacht Charter

1. Determine when you want to go on a Key West Bareboat Charter

Knowing when you plan to travel helps determine the cruising grounds you should be considering. Prices, availability and particularly weather, can all vary depending on the time of year and can play an important part in choosing a Key West Yacht Bareboat Charter destination.

2. Determine what type of Bareboat Charter in Key West

Is this a family holiday, quiet romantic getaway, a couple’s or singles trip, etc.? This will determine what type of boat and crew would be suitable, and what islands to visit or activities to plan for on a Key West yacht Bareboat Charter

3. Determine where you want to go on your Bareboat Charter Key West

Yacht charters are available around the globe with The Caribbean and Key West being the most popular. After hurricane, Irma and Maria’s devastation in the Caribbean more potential bareboat yacht charter customers are looking to Key West.  The Dry Tortugas and Fort Jefferson remains the most popular destination from Key West for a Bareboat Charter.  https://www.nps.gov/drto/index.htm

4. Determine your Key West Bareboat Charter budget.

Price plays a part in most people’s yacht charter. Our staff will help you maximize your budget and may in fact help you get more yacht than you thought possible for a Key West Yacht Bareboat Charter.

5. Determine what style of charter fits your Bareboat Charter Key West.

There are 3 types of a boat charter in key west:, – a crewed yacht charter:.

Your yacht comes with a permanent captain and cook. Price includes all meals and often house wines and open bar. Meals are prepared to your taste (to a very high standard) from individual preferences given to the cook before the charter. You choose the day’s activities and the itinerary, on a day to day basis. Yachts tend to be more luxurious and have more ‘toys’ (kayaks, waterskis, A/C, entertainment centers, etc) than a bareboat charter. The cost per person can be close to or less than the cost on a crowded cruise ship. Matching your party to a suitable crew is an important part of our service. Blue Ocean Yacht Charters currently does not offer Crewed Yacht Charters.

– Bareboat Yacht Charter Key West:

Sail the boat yourself. The principal charterer needs to have skippering experience on a yacht close to the size you are chartering. Equipment standards and reliability can vary considerably, even within a company. It is a mistake to choose a boat purely by price and the cheapest boat is not always the best value.

You can also charter through a bareboat company and add a captain (and cook). This is the ideal way to bareboat charter in Key West. Let us help you find a captain that is familiar with the boat and sit back and relax. Most captains will allow experienced sailors to operate the yacht on their own under the supervision of the captain. Typically boat owners will allow a lower deposit if a bareboat charter customer hires a captain that is familiar with the boat.

Now that you’ve decided the boat charter Key West, the fun really begins. There are so many yachts for you to choose from. Which one is right for you? Our staff knows each and every one of them, and once we know your desires for a dream yacht charter, Blue Ocean Yacht Charters will handle Step 6 for you.

6. Research & narrow your Boat Charter Key West choices.

Our staff will make suggestions and help you narrow down your private boat charter choices. We will do this based on your requirements and our personal knowledge of each boat and cruising ground.

7. Interview the prospective crews and recent charterers.

For a crewed charter, we feel the selection of the crew is actually more important than the boat. A good crew can make up for a mediocre boat but the opposite is not true. We maintain relationships with all yachts and closely monitor feedback from our recent charterers, so we are in an excellent position to find the perfect match for you and your guests.

For bareboat charters, the condition of the boat and the back up services provided by the company are very important as well.

8. Once you’ve decided, inspect the current condition of the yacht.

Any boat and /or crew can look good in a brochure or website. Some are immaculate and some are maintenance nightmares. 3 years of bareboat chartering can cause the same wear as 10-15 years of private use, but with a crewed yacht, maintenance is more important than age. We have inspected every boat you are chartering and can describe its current condition in Key West for a bareboat charter.

9. Arrange the other details.

You’ll need hotel reservations, provisioning options, customs and passport requirements, itineraries, airline tickets, etc… We can recommend and/or handle all of this for you and because of our volume discounts, can probably save you money by bundling your airfare with your Key West yacht charter.

10. And finally…step on board.

Put on your sunglasses, take off your sandals, relax, unwind and enjoy on a private boat charter in Key West.  You’ll be remembering this vacation for a lifetime. For real peace of mind, let us do it for you.  https://blueoceanyachtcharters.com/our-yachts/

Have a fun bareboat charter and be safe.

“Charter Booker!”

(Charter Booker, manages Blue Ocean Yacht Charters in Key West and writes many of the company’s blogs.  Having experience both on the water and off the water helping customers experience the best possible yacht charter for many years.  Charter Booker carries American Sailing Association certifications and has extensive knowledge of boat safety and regulations.  Call 305-923-4152 and ask for “Charter Booker” when booking your next yacht charter with Blue Ocean Yacht Charters in Key West, Florida.)

Captain Charter

Sit back and relax on your own private yacht while a professional takes the helm to show you the best of the Florida Keys. We offer multi-night yacht charter vacations. All of our Captain Charters have a minimum of 5 days/4nights which is the ideal amount of time to experience one of our Florida Keys sailing itineraries . Learn more about what to expect aboard a Captain Charter with Florida Yachts Charters.

Captain Selection

Captains, cooks & mates, life aboard, family friendly & kids aboard.

We are required under USCG regulations that define bareboat charter to allow you to choose your own captain. We will not assign one for you. We can provide more information of those captains who are familiar with our operations, the waters of the Florida Keys and our vessels. Should you already have a captain we require they complete our captain’s application for approval.

Captains, Cooks & Mates, Oh My!

Unless you are on a sailing course, when you interview potential captains to hire for your charter, they will ask you about prior boating experience and your ability in assisting with things like, picking up moorings balls, anchoring, dock lines and ability to manage the vessel in an emergency situation . If no one aboard would qualify to fulfill the role of 1st mate they will require you also hire a mate. Some mates can act as cook for an additional rate while others are only able to act as a mate. Adding a cook means they take care of all the meal planning, provisioning, cooking and clean up, a splendid addition to your experience. If you are unfamiliar with provisioning and cooking aboard a vessel this is a highly recommended choice.

Captains generally charge $450-500 a day, first mates $250 & Cooks $275.00, plus their food & beverages. For Cooks, they charge a full day for planning & provisioning time before your charter start. A 15 – 20% gratuity is industry standard for services well rendered.

Life Aboard a Captain Charter in the Florida Keys

Life aboard a yacht in the Florida Keys can take you to some beautiful anchorages, snorkel sights and secluded beaches. Your yacht will have all the comforts of a boutique hotel. The galley has just about everything your kitchen at home has so cooking aboard will be seamless. Refrigeration aboard vessels is much smaller than at home, and monohulls have very tiny freezer space. While all our vessels are equipped with Generators and ACs for comfort at anchor, while underway you will not be able to run the Generator, therefore you will not have AC until you reach a mooring ball or anchorage for the night. Most guests open the hatches while underway for a nice tropical breeze. As a result of Covid, we have taken the decision to not supply masks & snorkels for safety reasons over sanitation. We do sell good qualify snorkel/masks set and rent fins. We have local companies that can rent paddleboards & kayaks.

Families & Kids Aboard your Captain Charter

Key West & the Florida Keys is a great family friendly boating destination. The captains in this area know all the best places for spotting dolphins, snorkeling and a relaxing night at anchor. For safety reasons there are few things to note about having kids aboard when considering a captain charter with children:

• Bring along or plan to buy children’s life jackets. They are weight specific up to a certain age and we don’t offer them. Children are required to wear a life vest at all times while on deck, if your children have never worn a life jacket we recommend purchasing ahead of time and practice wearing, otherwise they will be stuck below deck with an adult.
• Our captains are professional and great with kids but it is important that a parent, guardian or designated adult keep an eye on them at all times. Your captain and mate will be very busy attending to navigation, sailing, and everyone’s overall safety and should not be relied upon to be watching children should you be absent. There are many things for kids to bump their heads on, interesting buttons to push and lines to grab. An interesting tip we recently read to ensure authority has been passed from one parent/guardian to the next is to use the phrase “Your Jane and John” and make sure the other adult responds “My Jane and John;” inserting your kids names into this phrase of course. This way you know that they know you are no longer watching the kids. If you are a pilot you may be familiar with this tip, as it was modified by parents who were former pilots for around the water safety at home.
• It may also be a good idea to talk with your kids (depending on the age) about power, water and toilet management. You will potentially be away from the dock for several days at a time. All our vessels are equipped with Generators and AC’s but these items are additional amenities and should there be a mechanical failure you may not have access to additional power and AC until it can be repaired. Depending on your itinerary you may also be without WiFi or cell phone access from time to time.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

KEEP IN TOUCH

Destination and charter fleet updates, special offers, and more

(305) 831-4125

Welcome Aboard Motor Yacht 42!

Private luxury charters aboard a 60ft Angel Motor Yacht

The Ultimate Key West Experience

Yacht 42 provides the perfect entertaining space to celebrate special events such as birthdays, anniversaries, weddings, or just treat yourself to something special.

A Unique Adventure

Escape the crowds, have your day tailored exactly as you like it, and make memories that will last a lifetime

Save 23% by booking online

Excursions and Private Boat Charters in Key West, FL

Spend the day where the locals hang out with our charters in key west.

Enjoy the fabulous, pristine waters of the Gulf of Mexico and straits of Florida from a beautiful powerboat. Mermaid Charters in Key West offers customized, private excursions that will make your Florida vacation truly memorable. Enjoy fun in the sun, visit a Key West sandbar, beach trips, and lunch trips, snorkeling as well as gorgeous sunset cruises. Book online! 

Spend the day where the locals hang out!

Enjoy the fabulous, pristine waters of the Gulf of Mexico and Straits of Florida from a beautiful powerboat. Mermaid Charters offers customized private excursions that will make your Key West vacation truly memorable. Enjoy fun in the sun, beach trips, and lunch trips, snorkeling as well as gorgeous sunset cruises. 

Explore Our Key West Boat Charters!

• Users Up to 6 People
• Hour Glass 4 Hours
• User All Ages

Sandbar Excursion

Enjoy the day miles off of Key West, at an Island or sandbar that only locals know about. Experience the ocean breeze and the beautiful turquoise waters in the Florida Keys. This is the #1 thing to do when visiting the keys. Fun in the sun for the whole family.

Snorkeling Excursion

Meet colorful marine life with an exclusive Key West snorkeling tour! Join us for a private charter to the best snorkel spots on the island. Don’t worry — we’ll provide the gear. Book online today!

• Hour Glass 3 Hours

Snorkeling & Sunset Excursion

Snorkel Key West with the best views of the sunset! This private charter is perfect for groups of up to six people. Join us by booking your charter online today.

• Hour Glass 4-5 Hours

Combo Excursions

Why not have the best of both worlds? Join us for the best Key West snorkeling along with a trip to the sunny Boca Grande island. This Key West vacation package is great for everyone! Book online.

Sandbar & Sunset Excursion

This is a fantastic way to spend a day in the sun. You will arrive by boat at a sandbar, where you can relax on the sand and soak up some rays. You can paddle-board and dolphin watch to your heart’s content. Then end the day by enjoying the sunset.

Geiger Key & Boca Chica Sandbar

Take a trip to Boca Chica sandbar and enjoy local bites along the way! Join us for a stop at Geiger Key Marina RV Park  and Fish Camp in Key West on this water adventure. Book online!

• Hour Glass 2 Hours

Sunset & Dolphin Watching Excursion

What can be better than watching a Key West sunset with dolphins swimming by? Join this sunset dolphin cruise in Key West for the perfect, romantic evening. Book online!

• Hour Glass 5 Hours

Tiki Bar, Snipes, Sandbar & Sunset

Sail out to a local tiki bar, a sandbar, and more! Enjoy this fun boating excursion for the best bites and time on the water. Book your tiki bar in Key West charter online today!

Tiki Bar, Sightseeing, & Boca Chica Sandbar

Enjoy marine life, island food, Tiki Bar cocktails, and sightseeing as you travel around the island, and take a quick dip at a nearby sandbar. Cocktails and island cuisine are available for purchase at the stop location, and you’re welcome to bring your own snacks and drinks on board.

Swimming, Sightseeing, Dolphin Watching

Swim with local marine life including dolphins, sea turtles, and manatees! This two-hour charter is perfect for exploring the Key West waters. Book online today!

• MOST POPULAR!

Island Excursion & Dolphin Watching

Sail away with us to an island only the locals know about! Our dolphin tour in Key West will be a memorable experience for you and your whole crew. Explore the Key West islands by booking your charter online.

Have fun in the sun with private boat charters in Key West!

Mermaid Charters in Key West is locally-owned and family-operated with our captains who bring more than 30 years’ experience with them on every adventure. We are committed to having fun, and always make sure you have a blast while avoiding the tourist crowds.

Delight in your best Key West boat charter ever when you join us aboard our amazing 30-foot scarab boat with twin engines, capable of accommodating six passengers comfortably. Enjoy a private boat charter in Key West and customize your adventure while motoring around Key West and reaching offshore destinations in complete safety.

Why people love to go out with Mermaid Charters in Key West!

"Had an awesome time with Mike. Super laid back and accommodating. Would 100% recommend this trip and the next time I am in Key West I plan on going again."

"We had an amazing day! Mike our captain took us to Boca Grande. Saw stingrays and much sea life . They were very accommodating as we added time onto our excursion. Can’t wait to go back!"

"Mike did a wonderful job! In fact, we’ve already booked another excursion with him. The island was beautiful and he was extremely knowledgeable. Thanks for a wonderful time."

"Captain Mike took us on a harbor tour, and then to a sandbar to chill on the beach and play on the Lillypad. Weather was iffy when the trip started, but it quickly cleared and turned out to be a beautiful day."

"Mike treated 5 of us to a area where we could either sit on the beach or sandbar. He also had the stuff to do a little snorkeling so some took advantage of it. Will definitely call them again on our next trip"

"Prompt and courteous, Capt Mike delivered a beautiful and memorable sandbar excursion which included visiting with dolphins! The boat ride was superb! Highly recommend Mermaid Charters."

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Charter Type Charter Type Deep Sea Fishing Charter Flats Fishing Charter Private Custom Charter Sailing Charter Large Group Charter Overnight Charter Sunset Charter Boat Rental Dry Tortugas Charter Luxury Yacht Charter Cuba Charter Jet Ski Rental Spearfishing Charter Snorkeling Scuba Diving Glass Bottom Boat Dolphin Watching Corporate Boat Party Lobstering Charter Wedding Charter Film Production Charter Other

Duration Duration Half Day (4hrs) 3/4 Day (6hrs) Full Day (8hrs) Multiple Day

Number Of Participants Number Of Participants 1 2 3 4 5 6 More Than 6

Location Location Key West (Lower Keys) Islamorada / Marathon (Middle Keys) Key Largo (Upper Keys) Dry Tortugas Cuba Other...

Date(s) Of Charter

Best Key West Boat Charters

#1 in key west boat charters.

   Hello and welcome to the best boat charter site in beautiful Key West Florida. With over 100 years of charter experience in the Key West waters, our crews provide that local touch you just can’t find anywhere else. I guess you could say Key West boat charters are just in our blood!

   Private charters, sunset sails, Dry Tortugas, boat rentals, fishing and more, no matter what boat excursion you’re seeking we’ve got you covered. Catering to our guest’s every need is just a part of what makes our Key West boat charters the best in the business.

   So make yourself at home and feel free to browse our site with confidence, knowing you’ve made the right choice.  We make it our personal mission to provide our guests with a charter experience of a lifetime. Thanks for choosing Key West Charter Boat and welcome to the Florida Keys.

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Boat & Catamaran charter in Key West - Yacht Rental

Key west yacht rental.

First Paragraph: Welcome to Yachting.Rent, the leading yacht rental service in the idyllic paradise of Key West, Florida. Nestled at the southernmost point of the U.S., Key West offers a tropical haven with its turquoise waters, vibrant coral reefs, and a rich tapestry of maritime history. At Yachting.Rent, we provide you with the unique opportunity to experience this spectacular world from the luxury and comfort of our top-tier yachts. Our fleet, ranging from intimate sailboats to opulent mega-yachts, is meticulously maintained and tailored to suit every occasion, be it a romantic sunset sail, a weekend getaway, or a grand celebration at sea.

Second Paragraph: Our dedication to excellence extends beyond our vessels. Our professional team, armed with extensive local knowledge and a passion for the sea, is committed to making your yachting experience memorable. Whether you’re navigating the serene backcountry waters, exploring the vibrant marine life at the reef, or simply lounging under the sun on the deck with a cocktail in hand, we ensure every moment is perfect. From the moment you step aboard to the time you disembark, our crew is at your service, providing expert guidance, sumptuous cuisine, and insights into Key West’s hidden gems. Safety, luxury, and unforgettable experiences are the pillars of Yachting.Rent.

Third Paragraph: But why choose Yachting.Rent? Because we believe in crafting personalized adventures. No two journeys are the same, as we mold each charter to reflect your desires. Additionally, our partnerships with leading marine and local businesses allow our guests exclusive access to some of the best spots and experiences Key West has to offer. Book with Yachting.Rent today and embark on a journey where pristine waters, unparalleled luxury, and cherished memories await. Dive into the Key West adventure you’ve always dreamt of, and let us be the key to unlocking your perfect maritime escapade.

Daniel Goldman

CEO of Yachting.Rent

Boat & Catamaran charter in Key West

Bali 4.5 – 4 + 2 cab. – Adria Chicha – 2017

Lagoon 450 F – 4 + 2 cab. – Shiva – 2018

Lagoon 42 – 4 + 2 cab. – Hanselli – 2024

Lagoon 42 – 4 + 1 cab. – pirelli – 2024.

Saxdor 320 GTC – Olivia – 2022

Saxdor 320 gto – kali – 2022.

Why Choose Us

Yacht charter in Key West

Yachting.Rent presents an unmatched yacht charter experience in the heart of Key West, Florida. Situated in one of the most enchanting spots on the U.S. coastline, Key West boasts crystal-clear waters, rich marine biodiversity, and a myriad of aquatic adventures waiting to be explored. At Yachting.Rent, our primary mission is to transport you into this maritime paradise aboard our exquisite yachts, offering you unparalleled views and unrivaled comfort. With a diverse fleet ranging from sleek sailboats ideal for intimate outings to luxurious mega-yachts designed for larger gatherings, we have the perfect vessel to suit every traveler’s taste and occasion.

As the premier yacht charter in Key West, Yachting.Rent prides itself on offering more than just a boat ride; we provide an immersive experience. Our seasoned crew is not only trained in navigation and safety but is also deeply familiar with the hidden treasures of the Keys. Whether you’re keen on diving into the depths to witness the vibrant coral reefs, cruising along the shimmering waters to catch a glimpse of dolphins, or anchoring at a secluded spot for a serene sunset, our team ensures your journey is tailor-made to your wishes. Gourmet meals, refreshing beverages, and guided activities are part of the package, ensuring that your time aboard is as enjoyable and relaxing as possible.

What sets Yachting.Rent apart from the rest is our unwavering commitment to personalized service. We understand that every guest has unique expectations, and we thrive on exceeding them. With exclusive tie-ups with top-tier marine and local establishments, our charters offer access to experiences that are both rare and mesmerizing. So, when you choose Yachting.Rent, you’re not just booking a yacht; you’re reserving a gateway to the many wonders of Key West, with every journey tailored to evoke a sense of wonder and create memories that last a lifetime. Dive deep into the essence of Key West with Yachting.Rent, and let your nautical dreams set sail.

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Why is Key West a good sailing destination?

Yachting.Rent proudly stands as an ambassador to one of America’s most cherished nautical playgrounds: Key West, Florida. This sun-kissed haven, located at the southernmost tip of the continental U.S., is not just a place but a feeling, an invitation to experience the dance of the waves and the call of the open sea. Key West isn’t just a destination; it’s a state of mind, a dream for sailors and maritime enthusiasts, offering a combination of nature’s beauty, historical charm, and maritime adventure.

To begin, the geographical location and natural attributes of Key West make it a sailor’s dream. Nestled between the Gulf of Mexico and the vast Atlantic Ocean, it offers a unique blend of calm, turquoise bays and challenging open-water passages. The nearby Gulf Stream ensures a temperate climate year-round, which means consistent sailing conditions. Then, there’s the rich biodiversity. The coral reefs of Key West, such as the famous Florida Reef, are among the most diverse ecosystems in the northern hemisphere. Sailors often find themselves accompanied by playful dolphins, curious sea turtles, and a colorful array of fish, turning every voyage into a nature documentary come to life.

But Key West is more than its natural wonders. Its history is intertwined with tales of pirates, smugglers, and treasure hunters. The island has been a muse for writers, artists, and adventurers for centuries. Sailing here allows one to retrace the paths of old sea captains, explore sunken treasures, and dock at historic seaports where tales of yore come alive in rustic bars and charming boutiques. With Yachting.Rent, every journey can be infused with these stories, making the sailing experience as culturally rich as it is visually stunning.

In conclusion, Key West is not merely a point on the map but a portal to a world where nature, history, and adventure meld seamlessly. Whether you’re a seasoned sailor seeking new challenges or a novice looking to experience the magic of the sea for the first time, Key West promises a journey like no other. And at Yachting.Rent, we’re dedicated to ensuring that this promise is not just met but surpassed, offering curated voyages that capture the essence of Key West in all its glory. Join us, and let the winds of Key West guide your next adventure.

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What Choose

Sailing boat or Catamaran, what to sail in Key West

At Yachting.Rent, we cherish the spirit of exploration and the thrill of experiencing the azure waters of Key West, Florida. As you prepare for a maritime adventure in this tropical paradise, a quintessential question often arises: should one opt for a traditional sailing boat or venture aboard a catamaran? Both vessels offer distinct experiences, and understanding their nuances will help you tailor your Key West journey to your heart’s desires.

Traditional sailing boats, with their sleek hulls and iconic silhouettes, are an ode to the age-old art of sailing. They resonate with the rhythmic dance of the waves, letting sailors feel every ebb and flow of the ocean. Sailing boats offer an intimate connection with the sea, making them perfect for those who seek a genuine and tactile sailing experience. The sensation of heeling, where the boat tilts as it harnesses the wind’s power, can be a thrilling aspect for many. Furthermore, with their deeper drafts, these boats can often access unique routes, navigating narrow channels and anchoring close to hidden beaches and coves. If you’re looking for an authentic sailing experience that connects you closely with Key West’s marine environment, a sailing boat might be your vessel of choice.

On the other hand, catamarans, with their twin hulls and broader decks, are synonymous with stability and space. These vessels offer a relatively flat sailing experience, minimizing the rolling and tilting common in monohull boats. This feature is especially beneficial for those who are new to sailing or are prone to seasickness. Catamarans also boast expansive lounging areas, both indoor and outdoor, making them ideal for larger groups or families. With shallow drafts, they can anchor closer to the shore, giving sailors easy access to the pristine beaches of Key West. If you envision your maritime adventure filled with sunbathing, snorkeling, and socializing in spacious comfort, a catamaran could be the answer to your nautical dreams.

In conclusion, the choice between a sailing boat and a catamaran comes down to personal preference and the kind of experience you seek in the mesmerizing waters of Key West. Whether you’re yearning for a visceral bond with the sea or a laid-back, luxurious voyage, Yachting.Rent ensures that your charter meets and exceeds your expectations. Join us as we set sail into the heart of Key West, letting the whispers of the waves guide your unforgettable journey.

Find inspiration for your next holiday

The California Coastline: A Sailing Adventure along the Pacific

Sailing in the Florida Keys: Exploring the Tropical Paradise

New England Sailboat Cruises: Exploring the Historic Coastal Cities

Island-Hopping in Hawaii: Discovering the Aloha State by Sea

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7 Best Key West Private Boat Charters In 2024!

by waynekask | Mar 20, 2024 | Blog , Key West | 0 comments

Last Updated on March 20, 2024

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Are you looking for the top Key West private boat charters? If so, you’ve come to the right place!

Whether you’re looking for a half-day or full-day charter, boat trips to a private island, or a crew offering the most perfect hospitality, this list has something for you.

As an expert on Florida travel and a Sunshine State fanatic, I’ve carefully curated this list of Key West private boat charters to include only the best of the best.

Let’s dive in!

Don’t Have Time To Read The Full Article? Book The Private Half-Day Key West Boat Trip   with a 5 ⭐️ rating

Our Top 3 Picks: Key West Private Boat Tours!

Private Half Day Key West Boat Trip

Private Sand Bar Cruise On A Tiki Bar Boat

Private Wind & Wine Sunset Sail In Key West

Best Key West Private Boat Charters!

1. snorkel, sandbar & dolphin excursion in a glass-bottom boat.

Photo Credit- Floridays

Tour Rating: 5 Stars ⭐️⭐️⭐️⭐️⭐️     Length: 3.5 Hours      Check Rates Here

Make your Key West vacation extra special with one of the most distinctive charter boats available: a glass-bottom boat .

There is no better way to see Florida’s coral barrier reef and fabulously diverse sea life than through the glass on this private charter with your own captain.

Enjoy a day trip into the Florida Keys National Marine Sanctuary to snorkel.

All the while, your crew will share their wealth of local knowledge about the ocean.

Next, you’ll head to a remote island where you can explore, paddleboard, snorkel, or float in the crystal blue waters.

If you’re lucky, you may even get in some dolphin watching!

This unique experience gives you the opportunity to enjoy aspects of the natural environment many tourists never see.

Here’s what a past guest said about this tour:

“This was the single best charter boat experience we’ve ever had. Ashley, the captain, was stellar… Ashley is a great captain and she’s fun intelligent and interesting, but she also knows her craft… Of all the things we did in Key West, this was absolutely the highlight of the trip and worth every penny… Such a fantastic experience.”

Melody_K ⭐ ⭐ ⭐ ⭐ ⭐

✅ What’s included in this tour: 

Bottled water

Use of Snorkeling equipment

Cooler with Ice

Book this Snorkel, Sandbar & Dolphin Excursion In A Glass-Bottom Boat

2. Private Wind And Wine Sunset Sail In Key West

Photo Credit- Danger Charters

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 2 Hours      Check Rates Here

Turn your trip into a special occasion with a private sunset cruise in Key West .

Spend two hours relaxing on a 65-foot schooner near Opal Key Resort with great music and even greater views. 

Soak in the views while you sip on international wines, beers, and non-alcoholic beverages (full bar style).

Snack on delicious hors d’oeuvres, take pictures and chat with the crew.

Watch a spectacular sunset over the waters of Key West to finish off a perfect day.

Sophistication and beauty define this private sailing charter. You’re sure to have an amazing time.

Note: The departure time is just before sunset.

“This is the second time I went on the Wind and Wine Sail… it’s top-notch customer service and not too crowded. The wine and snacks are great and the crew is so personable. Definitely recommend this trip!!”

Tripadvisor Reviewer ⭐ ⭐ ⭐ ⭐ ⭐

✅ What’s included in this tour:

Alcoholic Beverages

Hors d’oeuvres

Book this Private Wind And Wine Sunset Sail In Key West

3. Private Dry Tortugas Luxury Charter In Key West/ Lower Keys

Photo Credit- SeaEO – Nautical Ventures

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 8 Hours      Check Rates Here

Ready for an unforgettable experience? If so, step aboard this Luxury Charter full-day tour to ensure you have enough time to do everything you want.

The captain and crew will tailor the boat ride and itinerary to your preferences.

Whether you’re looking for an intimate experience involving sunsets, want to spearfish your own lunch, snorkel above a coral reef, or visit your own private sandbar, the decision is up to you!

One option is to head to the remote and beautiful Dry Tortugas–a group of islands featuring an exceptional natural habitat.

Here you’ll find glorious white sand, beautiful waters, and historic Fort Jefferson.

It’s the perfect destination for an all-day adventure and is on many people’s bucket list.

When it comes to full-day charters in the lower Florida Keys, this is definitely one of the best.

“We had the most incredible afternoon with SeaEO and Carlos. He took us to a sandbar where we drank champagne in the ocean and watched the sun go down. Truly an unforgettable experience. Carlos tailored every moment of the experience to our wishes. We will call him every time we are in Key West from now on.”

Mary_C ⭐ ⭐ ⭐ ⭐ ⭐

Air-conditioned vehicle

Restroom on board

WiFi on board

Private transportation

Use of Snorkel equipment

Use of spear gun

  √ Book this   Private Dry Tortugas Luxury Charter In Key West/ Lower Keys

4. Private Luxury Sailing Catamaran Charter

Photo Credit- Bimini Charters

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 3 Hours      Check Rates Here

Wind, sea, and sails await on the private luxury catamaran tour .

Choose the best time for you, or opt for a dreamy afternoon sail over the crystal clear waters surrounding Key West.

Keep an eye out for sea turtles and dolphins, relax on the trampolines, or sip on cocktails while the breeze blows softly past.

You can also don snorkel gear and explore the underwater world.

This catamaran charter is a perfect way to enjoy a special day with your partner, celebrate family get-togethers, or simply celebrate life.

Rest secure in the extensive experience of your captain. This day will be worry-free and fabulous.

Snorkel, sail, and delight in the views on one of the most popular sailing charters available.

“Sitting in the netting of the catamaran and watching the water go by the snorkeling was awesome. We went out to the reefs. He was able to post up while we snorkeled.”

Jonathan_D ⭐ ⭐ ⭐ ⭐ ⭐

3-Hour Boat Tour

Book this Private Luxury Sailing Catamaran Charter

5. Private Half-Day Key West Boat Trip

Photo Credit- Native Sun Private Charters

Tour Rating: 5 Stars ⭐ ⭐ ⭐ ⭐ ⭐     Length: 4 Hours      Check Rates Here

Have a blast on the gorgeous Key West waters on this private half-day boating experience .

This boat is a one-stop shop for pure  fun . You can snorkel among tropical fish, paddle board, make sandbar trips, or even enjoy a little fishing.

Whether you’re looking for a relaxing tour of Key West or jam-packed hours of activity, this tour could make for the best day of your life.

Charter lengths can vary from 2 to 8-hour day trips, but at 4 hours, this tour could be a perfect option.

It lets you enjoy the sunshine and sea but still have half a day for other activities or pure relaxation.

“You can’t go wrong with this excursion! Captain Tim was an excellent captain and guide!! His boat and the service he provided were top-notch. All of the equipment was in great condition, and he was very knowledgeable about the best places to go for the water activities we wanted to partake in. We would love to do this again the next time we’re in Key West!”

Sarah_S ⭐ ⭐ ⭐ ⭐ ⭐

Soft drink/Pop

Use of snorkel gear

Fishing gear

Paddleboard

Book this Private Half-Day Key West Boat Trip

6. Private Sand Bar Cruise On A Tiki Bar Boat

Photo Credit- Tiki Boat Adventures

Skip the chaos of larger group sailing tours and enjoy a great day on a private Tiki boat .

A tiki boat is the perfect vessel for bachelorette parties, groups of friends, and anyone who enjoys exploring.

Join one of these Tiki sandbar tours and sip or snack on whatever food or beverages you bring along.

Keep an eye out for dolphins, turtles, and other marine life as you cruise.

This tour passes by the US Navy facilities and cool landmarks, visits Jewfish Basin (an amazing area for wildlife), and cruises into the backcountry of the Florida Keys.

“What a great time! Plenty of shade aboard which was great. The captain was a stitch! Took us through just beautiful little islands where we swam and explored a bit. Perfect half-day trip!”

Kyle_H ⭐ ⭐ ⭐ ⭐ ⭐

Ice, Cups, water

Book this Private Sand Bar Cruise On A Tiki Bar Boat

7. Private Key West Sunset Cruise

One of the best experiences you can have in Key West is watching the sunset from the quiet waters of the Gulf.

Sail through a working harbor, explore mangroves, and even try your hand at fishing.

Next, your captain will take you to one of the best spots to see the sunset.

Gorgeous views and tasty snacks and sips make this sunset charter a fabulous choice.

If you’re ready, book your charter today and enjoy an unparalleled trip through North America’s natural treasures.

When it comes to multi-activity charters, the customer service and reviews set this private charter apart.

“Great night! Loved our experience. The boat moved slowly, we saw parts of Key West we hadn’t seen and learned a few things, too. The only negative was the boat is a bit older but it got the job done for a beautiful night watching a Key West sunset! Thank you!”

Suzanne_H ⭐ ⭐ ⭐ ⭐ ⭐

Book this Private Key West Sunset Cruise

Key West Private Boat Charters – Frequently Asked Questions

How much is a private charter in key west.

Private charters in Key West range from approximately $725 dollars per group of up to six people to $4,000 or more for a group of up to 15 people.

Private charters are a great way to experience the natural beauty of Key West.

How Much Does It Cost To Charter A Boat In Key West?

The cost of chartering a boat in Key West ranges from approximately $725 dollars per group of up to six people to $4,000 or more for a group of up to 15 people.

Can You Take A Private Boat To Dry Tortugas?

Yes! You can take a private boat to Dry Tortugas.

Simply check out  #3 on this list  and book your private adventure to the beautiful remote islands of Dry Tortuga National Park. It’ll be the adventure of a lifetime.

What Does A Private Charter Boat Mean?

A private boat charter is similar to boat rentals, but you won’t have to drive the boat yourself. 

Instead, you’ll have a captain (and sometimes additional crew) to man the boat.

You can enjoy a delightful day on the water without worrying about logistics or the technicalities of boating (and no massive size groups detracting from the experience).

You also get to decide where you want to go and what activities you’d like to do during the day.

How Much Does It Cost To Take A Boat To Dry Tortugas?

It costs about $200 per person to get to Dry Tortugas on the public ferry from Key West.

However, you can also get there via a private sailing catamaran. One  private charter option costs $1,899.00 per group of 12 people.

How Do I Get To Dry Tortugas Private Charter?

You can get to Dry Tortugas via a private charter by booking this  Private Dry Tortugas Luxury Charter in Key West/Lower Keys .

Final Thoughts: Key West Private Boat Charters

Have a great time away from home on these amazing Key West Private boat charters.

They are perfect for corporate events, family outings, and romantic getaways.

From yachts and catamarans to floating tiki bars and glass-bottom boats, this list has something for everyone.

Enjoy a day sailing through the Keys with the company of your choice.

Still Haven’t Decided? I Recommend Private Key West Half-Day Boat Trip  with a 5 ⭐️ rating

Booking a last-minute trip to Key West Florida?  

If so, we have you covered.  

Top Tours in Key West  – Viator

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