charter catamaran florida keys

What Should I Bring?

• Directions to Echo, Cruise Ship & K.W. Passenger Info

Key West Info

• Cancellation Policies, Terms and Conditions
• Catamaran Echo Videos
• ECHO Upgrades
• Tasting Notes
• Sunset Cruise

$10 Off each person – Promo Code “EchoDirect”

(for Public trips only – sold by the seat)

Catamaran ECHO 2

Current public & private trips – book here online, (free shuttle to the echo 2 dock from the perry hotel).

Catamaran ECHO 3

Custom private charters – text 305-304-2633, regularly scheduled public & private trips starting soon, …is a fast and comfortable sailing machine, providing the most stable ride on the water. naturally it’s a catamaran.

And with our big bimini top, you can get all the Key West sun or shade that you want. The fresh water shower on deck comes in handy on those hot days. A private bathroom in the cabin makes a day in the wildlife refuge civilized and helps protect our tropical waters.

ECHO 2 is located at the “Key West Historic Seaport” which is downtown in Old Key West at the famous Key West Bight. The Historic Seaport “Harbor Walk” goes right around the water’s edge and leads right to ECHO’s dock along side the famous “Boat House Restaurant at Turtle Kraals”. Spend the day on the Harbor Walk before and after your ECHO trip and visit all the great shops, restaurants and bars and galleries. This is where all the locals hang out!

So come and hang out in the coolest part of town and cruise with us at Catamaran ECHO ..

ECHO'S Official Website

Wild Dolphin

Snorkeling & Sailing Adventure

Click here to read more!

Private Day Charters

2 to 19 Passengers

Sunset Cruise - Adults Only

Private Trips Available (all ages welcome)

Towel (day trips), Sun screen applied (no oil), Hat, Camera, Sunglasses (polarized best), a jacket in fall, winter, spring (even if you think it’s warm out), a small bag to secure your things, a few bucks and a Big Smile!

Echo Upgrades

Please reserve upgrades in advance while reserving here online, or by phone or email before the trip.

Directions, Cruise Ship & K.W. Ferry Passenger Info

Certificate of Excellence 2019

Read Reviews

Call for Reservations

1-888-579-4782.

• Name * First Last
• Comments This field is for validation purposes and should be left unchanged.

Our Activities

Catamaran Echo - Wild Dolphins! Snorkel & Sailing Adventure

Catamaran Echo - Sunset & Moët Cruise

Catamaran Echo - Private Day Charters

Catamaran Echo - Private 2 Hour Champagne Celebration Sunset Sail

• Chesapeake Bay Itineraries
• Key West Itineraries
• Chesapeake Bay
• Virgin Islands
• St. Vincent & The Grenadines
• Browse our Fleet
• Meet Your Captains
• Charter Management
• Sailing Lessons

Key West Sailing Charters

Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

Our Key West Sailing Charter Fleet

Sailing cats.

Southern Cross

Fountain Pajot Elba 45

Dream Reach

Sugar Magnolia

Seawind 1260

Second sight.

Stay Glassy

Nautitech 40 open.

Ever Summer

Fountaine pajot my44, key west attractions.

Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

Yachts for Sale

Selling a Yacht

Tenders    &    Toys

Recent Sales

NEVER SAY NEVER AGAIN

Yachts for Charter

Destinations

Experiences

Charter Management

Charter Guide

Yacht Marketing

How to Charter

Superyacht Management

Crew Structure

Crew Management

THE WELLESLEY

Superyacht Construction

New Yachts for Sale

Yacht Design

Yacht Shipyards

Custom Construction

Built on Trust

Heesen 55m Steel

Benetti Oasis

Yacht Shows

News & Blog

Florida Keys Catamaran Yacht Charter

Catamaran yachts for charter in florida keys.

Browse a unique selection of Florida Keys Catamaran Yacht Charter and embark on the most exclusive luxury retreat. The tranquillity of cruising, coupled with the warm crew’s services, gourmet cuisine, and tailored itineraries, encapsulates the essence of opulence that Florida Keys is renowned for, creating unforgettable memories on the gentle Florida Keys tides.

Enquire On Florida Keys Yacht Charter

CONTACT OUR CHARTER BROKERS ABOUT CHARTERING IN THIS DESTINATION

Other Destinations

Rhode Island

YACHTS FOR SALE

YACHTS FOR CHARTER

CHARTER MANAGEMENT

[email protected]  

+377 97 77 67 57

SEO by The Agency

Yachts for sale

Selling a yacht

Recent Sale

Subscribe to our newsletter to receive our latest offers, news and the finest selection of superyachts.

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.

Bridging the space between reality & paradise.

A luxury sailing catamaran charter with an emphasis on fun and adventure.

Sailing from Ft. Lauderdale, The Keys & The Bahamas.

Come sail with us!

Meet The Crew

Captain -  Scott Clark

He is most at home when on the water.  He enjoys tinkering with everything, but has a flair for all things electrical. He loves sharing stories, creating videos and spending time with his wife and 2 sons.

First Mate - Holly Clark

She is most at home when she is spending time with friends and family. She enjoys cooking, meeting new people, yoga and snuggling with her granddog, Pugsly.

Check Out Our Latest Video!

The Ultimate Guide to an Unforgettable Key West Sailing Vacation

Fort Lauderdale Boat Charter Tours Made Easy, Fun & Affordable

Family Vacations are Incomplete without a Catamaran in the Bahamas

Boat Charter Rules That You Must Be Aware of!

A Day in the Life of a Charter Cat Owner

Mission Accomplished!

Our Mission

Tel. SAIL-TSB-DMB

(724) 587-2362, p.o. box 7696, sebring, fl 33872, ​ [email protected].

Thanks for submitting!

Key West Sailboat Charter Aboard the Tamboo

Our Fleet: the Tamboo

Bareboat charter ~ asa sailing courses*, ocean's edge marina key west, florida 2023 bali 42' sailing catamaran (bareboat only) 4 cabins - 4 toilets w/sinks - 2 showers 8 passengers max. or 6 passengers maximum if charterer selects and pays for a captain., *charterer selects and pays for an asa qualified captain for asa training..

Specifications

Cabins/berths Toilet w/sink Shower stalls

Beam Draft Water Capacity Fuel Capacity Engine

4 - (8 occupants max.)

23'6"

5' 227 US Gal 169 US Gal

2 x 45HP Yanmar

Interior Features

Air Conditioning

Interior Fans

Generator power

Solar power

Fridge/Freezer

Freshwater Filter

3 burner cooktop

Freshwater electric toilets

Exterior Features

Cockpit Cushions

Bimini Over Helm

Dinghy on Boat Lift

Forward Lounge

Swim ladder

Helm Lounge

Built in BBQ Grill

Fully Equipped Galley

Dishware, Silverware, Cutlery, Cooking Utensils

Serving bowls, platters, pitcher, cookware

Cutting Boards (*please provide your own cutting board, filet knife & cooler for fish*)

Small Appliances such as Coffee Maker,

Blender, Toaster, Microwave

Starter supply of paper towels, dish soap, fresh sponge

Linens & Things ​

Bed Sheets & Blankets (beds will be fully dressed upon arrival)

2 Bath, Wash & Hand Towels per guest

Starter supply of marine grade toilet paper

Navigation Equipment

Apparent wind indicator

Depth sounder

RAYMARINE AXIOM+ GPS/chart plotter

Hand Bearing Compass

Parallel rulers

Stereo/cockpit speakers

VHF mic at helm

Local charts

Cruising Guide to Florida Keys

Catamaran Sailing Vacations in Florida Keys: Upper and Lower Florida Keys - Dry Tortugas - Fort Lauderdale, Miami, Marathon and many different stops along the way! Charter a Catamaran with no crew and drive yourself or hire professional crew for your catamaran trip.

The florida keys have become a popular destination for americans looking for a tropical sailing vacation without leaving their own country. the florida keys can be considered the american caribbean and features all the same amenities as other island destinations such as world class sport fishing, scuba diving and snorkeling, boating, sailing, kayaking and eco-tours. each of the island destinations has some special features. we invite you to visit each area individually and discover the tropical paradise in the florida keys..

Receive the rate sheets for bareboat charter companies operating in this destination.

Fill in the quick form and rate sheets by company will be delivered instantly into your inbox. Rate Sheets do not reflect current promotions or discounts. We can send you detailed proposals and charter advice upon your request with discounts.

Florida Keys Itinerary

Keys - one week.

Upper Florida Keys - 3 Days

Lower Florida Keys - One Week*

Sailing from Marathon Key you will experience the many pleasures and sites of the Florida Keys. The unspoiled coral reefs of the Lower Keys have many sites where you can tie up to a mooring ball and snorkel or dive. Hawks Channel provides fantastic sailing, as there is protection from the ocean swells but still great wind.

Dry Tortugas - One Week*

Bahamas itinerary, chain in the bahamas.

Across the Gulf Steam from Florida's east coast lies the Bimini Island Chain. These sub tropical low-lying islands are a fantastic destination for a weeklong sail. Bimini offers some of the finest SCUBA diving, snorkeling, fishing and beachcombing anywhere. These "islands in the stream" offer water clarity, which is nothing less than spectacular. You may rent snorkel gear at our office in Ft. Lauderdale if you have not brought your own. For those who are certified divers we recommend renting your SCUBA gear from Underseas Sports in Ft. Lauderdale before you head across the Gulf Stream.

The Bimini Chain is lightly populated with the center of village life located on North Bimini, in Alice Town. There are many small restaurants, shops, and bars, as well as the Hemingway Museum at the complete Angler. Marinas are abundant if you decide not to anchor out. The beaches on North Bimini offer miles of un-crowded fine white sand and snorkeling from the waters edge. Golf Carts and Mopeds are available for rent so you can explore the island. One of the most interesting dive and snorkel sites off of North Bimini is "Bimini Road", which some say is the ruin of the lost city of Atlantis.

South Bimini is primarily residential with only two marinas. The new Bimini Sands Marina is located at the entrance to the harbor and has a Customs and Immigration office so you can clear in there without having to take a taxi and ferry over to North Bimini. The other marina is located at the south end of the island. A new channel has been dredged in Nixon's Harbor that takes you into the marina. Not far from the south end of South Bimini lies the wreck of the "Sappona". This is a great snorkel and dive site.

The only other island in the Bimini's with a marina is on North Cat Cay. This is a private Island with some "high profile" homeowners. For this reason the local authorities limit the accessibility of the island for non-members. You are welcome at the Marina for transient dockage but they prefer for you to stay in the area of the marina where there is a fine dining restaurant a store for provisions, dock bar, and gift shop. It is a truly beautiful setting at the marina and we recommend this for your last night in the Bahamas. Just off the coast of South Cat Cay is a fantastic dive site. "Tuna Alley" has mooring balls and is 50' to 80' with deep caverns and crevasses in the coral.

There are many other Anchorages such as Honeymoon Harbour, Dollar Harbour. Moxom Rocks, and Nixon Harbour. Please call to speak with our knowledgeable staff for more details.

One Week Itinerary to the Bimini Islands

Day three -, day seven -, day eight -.

Obviously there can be a lot of variation on this itinerary, but it shows there is plenty to do in a week charter to the Bimini Island Chain. If you would like further information or would like to plan a different Bahamas trip give us a call and speak with our knowledgeable staff. We can provide you with a cruising guide to the Bahamas Islands as well as charts of the area.

• Mediterranean
• South Pacific & Oceania
• South-East Asia
• Indian Ocean
• Northern Europe

Bareboat Monohulls

• Bareboat Motor Yachts

Bareboat Catamarans

• Crewed Yachts
• How our services work
• Multi-Database Searching
• Boat Charter Price Guidelines
• Free Charter Guide
• About Sail Connections
• Client Charter Reviews

Sail the Florida Keys

• Location Guide

Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

Browse our yachts for charter in Florida Keys

Bareboat Motor Boats

Fully Crewed Yachts

The sail connections guarantee.

One contact - every option - advice you can trust.

• Matching any competitive offer
• Sourcing boats with discounts available
• Personalising our proposal just for you
• Qualifying the operator as well as the boat
• Advising without bias based on 25+ years of experience
• We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.

Sign up and

GET 20% OFF

Your first boat rental

Welcome to Sailo !

Your code is:

Enjoy 20% off

• Explore boats
• Text +1 910-447-2456 Call +1 910-447-2456

Departure date

Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 3 catamaran charters in key west, florida.

Key West, FL

boating guide

In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

• 13 boat rentals in Key West, FL
• 13 boat rentals in Stock Island, FL
• 13 boat rentals in Key Haven, FL
• 13 boat rentals in Cudjoe Key, FL
• 13 boat rentals in Summerland Key, FL
• 13 boat rentals in Little Torch Key, FL
• 13 boat rentals in Big Pine Key, FL
• 10 boat rentals in Marathon, FL
• 10 boat rentals in Key Colony Beach, FL
• 10 boat rentals in Duck Key, FL

Catamaran Charters in Key West, FL | Sailo Boat Rental

Looking for a catamaran charter in Key West? Boat rental in Key West, Florida   is always a great way to enjoy sailing trip experience in Florida. Choose your perfect catamaran charter with Sailo and set a course for adventure! When you rent a boat in Key West, you can choose your own itinerary and explore at your leisure. Want to relax on deck? Prefer to do some fishing? Or maybe you just want to escape the crowds? Find your ideal yacht rental in Key West with Sailo.

Our finest collection of catamaran charters in Key West, FL

Key West, FL is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The catamaran rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 7 charters are currently available with or without captain, lined up in the Key West’s marinas, waiting for their guests. Rent a private catamaran in Key West with Sailo: it’s easy, quick, secured and the best choice for a fun experience in the waters of Florida.

How to find the ideal catamaran charter in Key West, Florida?

Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Key West, FL. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Florida, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much does it cost to charter a catamaran in Key West for a day?

Whether you are looking to rent a catamaran yacht in Key West for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Key West is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Can I pay in installments for my Sailo catamaran rental in Key West?

A lot of our boat owners allow payment in installments, particularly for the weekly charters. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Guidelines to responsible yachting

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto:  'Take only photos, leave only wake'  (OK, so we paraphrased). To be a responsible sailor, remember:

• Don’t disturb coral or sealife
• Take your trash home (and don’t throw anything in the sea)
• Respect the locals and their customs wherever you go

Read more about responsible boating.

• FAQ and Policies
• Accessibility Statement
• Boat Rentals
• Boat Calculator
• Discover Boating
• Community questions
• Referral Program
• Vivre: Furniture & home decor
• British Virgin Islands
• La Paz, Mexico
• Cabo San Lucas, Mexico
• Key Largo, FL
• St. Vincent and Grenadines

 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.  

Catamaran Charter Key West

Bare boat chartering for your keys family vacation.

Bareboat chartering, essentially renting a boat for yourself and your party, has been a popular vacation choice in the Carribbean for quite some time.  Bareboat charter destinations can be found world-wide yet many people don't know that you can do so right here in the US.  It is so easy to reach the Florida Keys by direct domestic flights or by road trip, and the vibe and environment is much of what you find in foreign tropical vacation destinations.

Experienced sailors with or without ASA certifications can qualify to bareboat with us and captain the catamaran on their own.  We will review your sailing resume prior to your charter date, and then include a 90 minute checkout sail upon your arrival to ensure you are fully confident handling your boat.  However, if you are not a sailor and are not comfortable piloting the boat yourself, you can still bare boat charter!  Right here on our website is a list of local captains you can hire to guide you safely to all the best spots in the Keys, on your own private cruise.

This is truly the most unique way to spend a week in the Florida Keys.  When you choose to stay in a hotel or short term rental, you are land locked and must separately hire day excursions to get out on the water and see some of our amazing sights.  With chartering, you take your accommodations wherever you go!  With full kitchens, grills, plenty of food storage space, cabins and bathrooms for the whole family, there is no need to eat out every meal, nor hire day trips to the top snorkeling locations.  Each boat is equipped with snorkeling gear for everyone.  Your week includes a Key West boat slip in one of the top rated, award winning Key West resorts , and all of its amenities, rentals, and excursions are there for your use, including free transportation to historic Key West.

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

Florida Keys Yacht Charter

Florida keys yacht charter guide.

A spectacular archipelago of over a thousand palm-fringed islands, Florida Keys are a natural paradise for exquisite sailing vacations. Boasting breathtaking coral reefs, azure waters, and gentle breezes, this is one of the world’s most captivating sailing destinations, making a Florida Keys yacht charter an adventure to remember.

From stunning beaches and snorkeling sites to abandoned sea fortresses, mysterious shipwrecks, and iconic bars once frequented by Ernest Hemingway himself, each Florida Keys island holds its own distinct charm and allure.

Yachts in the Florida Keys

Book your florida keys yacht charter here.

Please fill in this short form, and a member of our professional charter broker team will get in touch to arrange your exclusive yacht charter experience.

Reasons to Charter a Yacht in the Florida Keys

Home to bohemian artists, shipwrights of New England, wealthy merchants, and Cuban rum smugglers at one time, the Florida Keys still possess an atmosphere of irreverence and laidback island living – along with exclusive high-end resorts and premier marinas hosting luxury yachts.

Whether it’s enjoying a Rum Runner during the happy hour at Sloppy Joe’s or relaxing at the elite Palm Island resort, Florida Keys has got it all. Add incredible scenery, rich marine life, colorful reefs and fish, amazing beaches, and an array of excellent diving and snorkeling sites, and it’s no wonder why Florida Keys yacht charter experiences have few rivals.

Below, we share our top three reasons to charter a yacht in the Florida Keys:

Gorgeous Scenery

Pristine palm-dotted beaches, powdery white sand, and crystal-clear waters shimmering in hues of turquoise and aquamarine are Florida Keys’ signature scenery worthy of a postcard.

Tropical islands, the magical underwater world of coral reefs, and remote nature preserves matching the allure of the Everglades National Park set Florida Keys apart as a truly remarkable sailing destination boasting dreamy landscapes resembling Tahiti and the Caribbean.

Scuba Diving Heaven

Thanks to its proximity to the Florida Reef and numerous shipwreck sites, the Keys are a treasure chest for scuba divers.

From thrilling deep-sea diving to exploring artificial reefs of sunken warships to family fun snorkeling above the corals, no Florida Keys sailing vacation would be complete without experiencing its enchanting riches under the sea.

Colorful History

The Florida Keys has a unique cultural heritage stamped with Caribbean and Cuban influences, a colorful history of pirates, salvagers, and Prohibition-era smugglers, and the legacy of Ernest Hemingway, giving the islands an artsy, bohemian aura.

Whether it's visiting the famous novelist’s favorite watering holes in Key West or exploring abandoned ghost towns and sea fortresses dating back to the Civil War years, Florida Keys offer a glimpse into a different world of nostalgic Americana.

Featured Florida Keys Yacht Charter Destinations

While it’s easy to cruise along the Florida Keys chain, taking in the views and stepping ashore to explore the island lifestyle improvising the route as you go along, several Keys stand out as exceptional.

Below, we list some of the most iconic destinations for Florida Keys yacht charters:

Known for its vibrant atmosphere, historical significance, and artistic community, Key West has a character of its own. Sunset celebrations at Mallory Square, a pilgrimage to the Ernest Hemingway Home and Museum, and a night out on Duval Street are par for the course in Key West.

Unlike the glitzy, high-energy Miami Beach, Key West's South Beach and Higgs Beach are more laidback boasting soft white sands and crystal-clear waters perfect for snorkeling.

The island’s proximity to both the Gulf of Mexico and the Atlantic Ocean means excellent fishing opportunities.

Key West is also the end point of the Atlantic Intracoastal Waterway, a 1000-mile sailing route connecting New England and Florida famous for its beautiful scenery and spots few land-bound tourists get to see.

Marathon Key

Situated in the middle of the Keys, Marathon is perfect for nature lovers and water enthusiasts. The Dolphin Research Center, beautiful snorkeling sites, and stunning views from the Seven Mile Bridge are ideal for family fun, while adventure seekers will enjoy fishing for mahi-mahi and tuna.

Located just eighteen miles from the glittering Miami skyline and Biscayne Bay and home to the John Pennekamp Coral Reef State Park, Key Largo is a natural paradise for scuba divers. Located near the Florida Reef – the third-largest barrier reef in the world - Key Largo is a gateway into an extraordinary world of underwater wonders.

Natural coral and fish diversity aside, experienced divers flock to Key Largo to explore the shipwreck of USS Spiegel Grove, a warship purposely scuttled just off the coast of the island. Comparable to the world’s largest artificial reef, the USS Oriskany warship sunk in the Gulf of Mexico just off the coast of Pensacola, the USS Spiegel Grove shipwreck is a treasure trove for dedicated divers.

In addition to diving, snorkeling, and glass-bottom boat tours, Key Largo is known for its relaxed atmosphere and casual charm, along with cozy local bars and great seafood cuisine.

A bustling community in the early 1800s, Indian Key served as a thriving hub for shipwreck salvaging. During that period, ships would often run aground on the reefs around the island, and ingenious salvagers would come to the rescue of the crews and passengers – and claim the wrecked vessels for themselves.

Now, the island is uninhabited, lending it an eerie ghost town feel. History buffs will appreciate the opportunity to explore the ruins of the old settlement.

Accessible by boat or kayak only, Indian Key offers seclusion and tranquility, and its shallow waters, corals, and rich marine wildlife are ideal for snorkeling.

Plantation Key

Beloved by luxury yacht guests seeking authentic experiences, Plantation Key has a laidback atmosphere and is largely untouched by the hustle and bustle of the more tourist-saturated spots in the Florida Keys.

With easy access to Key Largo and Islamorada, Plantation Key is a great launchpad for water-based activities from kayaking and paddleboarding to scuba diving and fishing. The island’s Anne’s Beach is a popular highlight boasting shallow blue waters and a boardwalk stretching over seagrass beds.

Windley Key

A small but beautiful island with a charming marina, Windley Key is best known for its Fossil Reef Geological State Park, showcasing an ancient coral reef that dates back over sixty million years.

For nature lovers, Windley Key offers a network of scenic hiking trails, and its peaceful ambience provides a welcome break.

Bahia Honda Key

Home to the Bahia Honda State Park, Bahia Honda Key is renowned for its picturesque white-sand beaches, clear blue waters, and opportunities for snorkeling, hiking, and wildlife watching.

A virtually uninhabited tropical paradise, Bahia Honda is a perfect getaway in unspoiled nature and spectacular sunset views over the Gulf of Mexico.

Dry Tortugas

The westernmost island chain of the Florida Keys, Dry Tortugas hides unique treasures above and below the sea.

The Seven Dry Tortugas islands are home to the most pristine coral reefs in the region, abundant marine life, and sunken shipwrecks.

The island’s natural beauty aside, its key feature is the historic Fort Jefferson, a colossal fortress that served as a prison during the Civil War years.

When to Visit: Florida Keys Weather

Florida Keys is a year-round sailing destination thanks to its tropical climate. The best weather is between March and May, while the winter months and early spring are favored by sailing yacht enthusiasts due to stronger winds.

The only period to avoid is June through to November -hurricane season in the Atlantic Ocean.

The Cost of a Florida Keys Yacht Rentals

Yacht rentals in the Florida Keys have different price points depending on the charter boat’s type, size, and amenities on board.

A motor yacht with the capacity for 2-6 guests can cost between $25,000 - $45,000 per week. For charter yachts with larger capacity, expect to spend $60,000 and upward, whereas a luxury yacht charter with a professional crew (unlike bareboat charter) can cost anywhere between $100,000 - $200,000 per week or more.

Find Florida Yacht Charters That Offer the Right Features

Choosing a private yacht for that unforgettable sailing holiday is all about personal preferences.

Whether you hope to set sail and relax on the deck, jump into the water for action and adventure, or entertain a group of guests, it’s important to look for yacht charters with specific features to cater to your individual needs.

Here are some of the key luxury yacht features to consider:

Florida Keys is a paradise for swimming, snorkeling, diving, kayaking, and just about any other water sport. If you’re looking to experience the best of those azure blue waters, charter a yacht with jet skis, paddleboards, kayaks, foils, or snorkeling equipment on board.

Spacious Decks and Cabins

Comfortable, well-appointed cabins and spacious decks are a must on a luxury yacht, especially if you’re embarking on a longer voyage and expect comfort and easy access to the water.

A hot tub or a jacuzzi on deck enhances the sailing experience, especially on those breezy Florida Keys evenings when enjoying a sunset with a cocktail in hand.

How much is a charter boat in Key West?

While a day charter in Key West may cost between $2,500 and $5,000, most weekly yacht charters in the Florida Keys start at around $25,000 per week.

What is required to rent a boat in Florida Keys?

Unless you’re aiming for a bareboat charter, there’s no need for a boating license or sailing experience to rent a crewed yacht in the Florida Keys.

Destinations

Popular nearby yachts

Latest nearby yachts

Bareboat Charters

Bareboat charters. your sailboat. your experience.

Sail Away to Tropical Paradise: Explore the Florida Keys on a Well-Equipped Sailing Vacation

Picture this: a gentle breeze brushes against your face as you navigate the calm, turquoise waters of the Florida Keys. You’re at the helm of a beautiful sailing vessel, equipped with all the amenities you need to make your sailing vacation unforgettable. Whether you choose the Catalina 22′ for a day sail or the Morgan 33′ Out Island for an overnight trip, you can rest assured that your boat is well-equipped for your chosen adventure.

As you board your boat, you feel a sense of excitement and freedom wash over you. You’re in charge of your vacation – you get to plot your course and sail into tropical paradise at your own pace. The warm sun beats down on you, and you can’t help but feel grateful for this opportunity to escape the stresses of everyday life.

If you’re planning a multiple night charter, you can provision at one of the local chain supermarkets and enjoy your fully-equipped galley at your leisure. Or, if you’re just renting for the day, you can grab a packed lunch and set off on your adventure.

The Florida Keys offer a plethora of activities for sailors of all levels. From visiting underwater or land-based state and national parks to local beach bars and restaurants, there’s something for everyone. Take a dip in the crystal-clear waters, explore the mangrove islands, or relax on a secluded beach – the choice is yours.

Whether you choose the Catalina 22′, the Morgan 33′ Out Island, or one of our catamarans, you can rest assured that your boat is well-equipped for your chosen adventure. So go ahead, captain your sailing vacation in the Florida Keys and create memories that will last a lifetime.

Meet your yacht at our home in Soper’s Hole

“Know your charter is going to be perfect, without any drama.”

Experience exhilarating Sailing and Nature.

“Discover the Islands of the Florida Keys.”

“Morning Star Charters.”

Let the day Start and stop when and where you desire.

“The Perfect Getaway”

“Enjoy the feeling of being welcomed into the Morning Star sailing family”

Sailing at it’s best

“Morning Star Sailing Charters is the longest established Sailing snorkeling Charter company in the Florida Keys.”

Enjoy self-prepared meals from your well equipped galley while surrounded by incredible beauty

“All the water toys you could want, available to rent right here at Morning Star Charters.”

Morning Star Charters, Sailing, Snorkeling, Kayaking, Sunset Sails, Cottages and Sailboat Rentals in the Florida Keys / Key Largo. Sailing and land based Sailing Vacations.

Florida Keys Sailing

The Spanish first found the Keys during Ponce de Leon's expedition in 1513. They mapped and named the Keys principally as an aid to their ships, which, full of gold and silver, used the Florida Straits to go from the New World back to the Old. The first settlement was at Key West, in 1882, a little more than two decades before Florida became a state. The other Keys pretty much stayed deserted until 1874, when the government surveyed them. After the survey, the government plotted land for businesses and homes. The early homes were primitive. They were built from the local beaches, made of wood and other materials washed up from shipwrecks. In 1912 Henry Flagler built a railroad to Key West. This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade.

Condé Nast Traveler

The Best Places to Learn How to Sail, From the Greek Islands to the Florida Keys

Posted: March 21, 2024 | Last updated: March 21, 2024

Sailing is one of the best ways to explore some of the most beautiful, untouched coastal destinations around the globe. But from the outside, learning how to sail might seem like an intimidating—and expensive—pursuit.

However, learning to sail isn’t as difficult as it might seem. And contrary to what some may believe, “sailing is for everyone,” Zeke Quezada, the Director of Communications at the American Sailing Association (ASA) tells Condé Nast Traveler.

“It is important to understand that anyone can sail, and it is really easy to learn,” Quezada says. “Sailing is not just for the affluent; head into a community sailing club at your local marina, and you'll have options to get out on the water for little to no cost.”

While mastering the art of sailing takes consistent practice, hopeful captains looking for a crash-course to jumpstart their journey may consider a sailing vacation . These educational charters allow you to fully immerse yourself in the nautical lifestyle —and you can earn official certifications along the way. On these types of trips, “you have a qualified skipper on board who is offering instruction, as well as advice on how to become a safe and confident sailor,” Quezada explains. “The best part is that you can have your family onboard, and everyone is having a vacation while you check off the bucket list item of learning to sail.”

When planning your first sailing trip , look for trips and schools that offer credentialed schools and instructors; organizations such as ASA, US Sailing, and the Royal Yacht Association are internationally recognized. By following these certification tracks, you can become licensed to sail a charter without a captain on board, also known as a “bareboat charter.” Though not required in some places, a bareboat certification makes it much easier (and safer) to rent your own boat .

No matter which route you take, sailing is a lifelong skill that will open doors to a community of people passionate about getting out on the water and protecting the oceans. “Most importantly, you will learn how to sit back, turn off the phone, and feel the wind in your hair and the sun on your face,” says Quezada. “You might start listening to Jimmy Buffet as well.”

Below, we’ve rounded up the best places around the world for learning how to sail—including destinations in North America , Europe , Asia , and Australia —plus, the sailing courses and trips to book in 2024.

Sign up to receive the latest news, expert tips, and inspiration on all things travel

The Virgin Islands

The British Virgin Islands and US Virgin Islands are some of the best training grounds for novice sailors “because of their line-of-sight sailing, predictable wind, and sailor-friendly destinations,” Quezada says. “In the BVI, you can learn to sail and have a beach vacation simultaneously.”

If you’re looking to get your bareboat license, there are several ASA-certified sailing schools in the BVI and US Virgin Islands. Offshore Sailing School , one of the world's preeminent sailing institutions, offers fast track courses for all levels of sailing. Alternatively, charter a captained catamaran, one of the most popular ways to explore the Caribbean.

Florida Keys

Warm temperatures, calm turquoise waters, and consistent easterly winds make the Florida Keys one of the best places to learn to sail in the US. Stay at the Key Lime Sailing Club and cottages resort on Buttonwood Sound in Key Largo and take lessons at the American Sailing Academy , located onsite.

Alternatively, outdoor education organization Outward Bound, which offers program scholarships, is hosting a Florida Keys sailing excursion for adults in March/April 2025. Participants will live on a 30-foot open sailboat for slightly over a week learning beginner, intermediate, and advanced skills in chart and compass navigation, small boat seamanship, weather observation, and anchoring.

Greek Islands

Sea of Cortez, Mexico

New England

There’s no better way to experience a quintessential New England summer than by sailboat. The sailing season in the Northeast runs from April to October, with ASA and US Sailing accredited schools located in major metropolitans like New York City and Boston as well as coastal enclaves like Newport and Cape Cod .

For adults seeking a basic introduction to the sport, US Sailing offers “first sail” lessons in dozens of locations up and down the Eastern seaboard. Pull on a striped sweater, pack a bottle of rosé, and you’re good to go!

Croatia’s Adriatic Coast is home to a vibrant sailing community with picture-perfect weather conditions. Beginner sailors will appreciate the gentle winds of Dubrovnik, the Split Islands, and Kornati National Park , whose sheltered coves and bays supply calm and predictable winds. Enjoy incredible natural wonders only accessible by boat, like the famous Blue Cave.

Student sailors can earn beginner, intermediate, and advanced ASA certifications aboard 8-day learn to sail vacations in July, August, and September 2024. Hosted by American Sailing partner Sailing Virgins, the catamaran and monohull ships—each a minimum of 40 feet with 3-5 cabins—visit the Croatian islands of Brac, Korčula, Šćedro, Komiža, Vis, and Hvar.

Gulf of Thailand

Whitsunday Islands, Australia

More for you.

Lord of the Rings fans 'disturbed' after seeing 'freakish' character that was cut from final film

Flight attendant explains why you should always throw a bottle of water under hotel beds

Sky Coach Teresa Weatherspoon Speaks Out on Caitlin Clark Concerns

Popular craft brewery closes as owner files Chapter 7 bankruptcy

Urgent Windows security flaw lets hackers infect your PC over Wi-Fi — update right now

Man Spills Tea on Popular Cheeses That Contain Wood Pulp

Relationship Issues That Can't Be Fixed, According To A Licensed Counselor

Housing Market May Hit 'Breaking Point,' Economist Warns

Corvette Gets A New Boss

How many times can you wear pajamas, jeans and other clothes without washing them? Experts weigh in

Kansas City Chiefs Owner Shouts Out Taylor Swift at Event in Ohio: 'She Is Definitely Part of the Chiefs Kingdom'

BlackRock CEO Larry Fink has an important message for the next wave of US retirees — here's how he wants to solve the country's retirement crisis

These Are The 7 Things Stroke Doctors Say You Should Never, Ever Do

This Clever Marker Hack May Be The Key To Keeping Birds From Flying Into Your Windows

The most popular big dog breed in America—and see the rest of the top 30, according to data

The Ford V8 Engine That Was A Little Outside Of The Box

Republicans Handed New Immigration Legal Loss

Companies are cracking down on mouse jigglers

64 people missing and many rescued from 2 shipwrecks off Italy. At least 11 have died

Tennessee home for sale, built by former Disney exec, shocks internet with unique entertaining space