Choose your charter vacation in the American Caribbean.

Live Like a Local and Play Like a Millionaire!

Location, location, location our boats are docked in downtown Key West,
...walking distance from most attractions.

Whether it is a vacation getaway, a special anniversary, milestone birthday, or at sea wedding, choose the safe, beautiful turquoise waters inside the barrier reef of the American Caribbean and have your own key west sailing adventure. We can accommodate up to six persons per boat for either a stay and sail package or for an away from the dock excursion.

We have six main charters for your review. Pick your favorite, add or take away the amount of days you wish, the ones offered are only a suggestion. We have three yachts for you to choose from: Moondance, Obsession, and WildThing.

Key West Boat & Bed Charter

Our Stay/Sail Vacation Package

Staying aboard a sailboat can be a fun and memorable alternative to land lodging. Stay a weekend or a week or two. Since 1995 offering custom charters at this location, we have developed a presentation to accommodate the experienced boaters, or the novice who wishes to stay at the docks as an introduction to the sailing experience.

       Special rates offered for guests staying over 5 nights.

Master Cabin with California King

Live aboard one of our three sailboats and be in the midst of Key West's Historic Seaport. The entire vessel is yours alone to enjoy. Schedule your basic sailing included or upgrade for more sailing time.

All three vessels are laid out the same with a double cabin and private bathroom at either end, with a large living room / main salon in the center with 6 foot 3 inches headroom plus kitchenette/galley. Salon can double as sleeping for two singles.

Ask us about discounts for additional sailing while you are on board.

Photo of one of our boat's master cabin.

In addition, there is also a land-based facility with keyed private bathrooms and showers with laundry. Drive in and park, leave your car, board your vessel and you can rent alternate fun transportation on your own and explore Key West, by walking, on a bicycle or a scooter. Electric cars are available as well. Fly into Key West; it's a 2 mile taxi ride. Ferry boat from Ft. Meyers to Key West. The boats are within view of the ferry terminal.

The Key West Boat and Breakfast Charter can be designed to meet your needs and schedule. There is a bimini shaded top to protect you from the sun on deck or choose to enjoy the famous sub-tropical sun lounging on deck. Sailing is naturally included with your charter. Meals are only provided on sailing excursion charters. It's your Key West Time, tell us your charter design or choose from our list of choices. We treat you as if you are the sailboat owner. Live the dream.

Tall ships garnish the harbor. Schooners flavor the setting with century old tradition. The marina has a desirable and comfortable 360 degree protected harbor for a quiet, motionless berth, close to restaurants, bars, a swimming pool and shopping.

Dante's Restaurant, walking distance from where we are docked.
(photo above) Dante's Restaurant

The boats are ideally located three blocks from Duval St. and the Sunset Festival at Mallory Square. All around your vessel are several restaurants, a swimming pool, music and lots of shopping plus museums nearby. Fort Zachary Taylor State Park is a colorful fifteen-minute bicycle ride to a sandy beach on the open ocean and a picnic area in a forest of whispering pines.

Discover the simplicity and unique world of sailboats. On your sail, your captain will allow you to take the helm and work the sails to experience sailing under his or her watchful eyes.

Key West Boat & Bed Pricing


$375 per night


$475 per night


$475 per night

Boat and Breakfast pricing is based on double occupancy; an additional charge of $45 per person per night over two applies; 6 person maximum per boat.

For the best in specialty lodging, call 305-304-4911

The Key West Sampler

It is the Key West Experience at its best; combining dockside enjoyment on your own sailboat in the Historic Seaport Days 1 & 3. Day 2 you go sailing, snorkeling, beaching, fishing on your own sailboat with our experienced captain and mate when at sea with all your meals while away from the dock.

Day 1-arrive and "kick back", take in the sights and sounds of Old Town and downtown, buy cocktails or sandwiches from a nearby restaurant, jump in their pool with a waterfall. Down Town is just 3 blocks away. Be comfortable; get to know your sailing vessel, lay out on the deck. You will have time to see some of the famous nightlife of Key West or just 'chill' on board.

Day 2- after you have breakfast on your own, captain and crew arrives with the provisions you choose, ready for a 24-hour sailing excursion. Departure is usually around noon sailing off to the reefs for viewing or snorkeling on your way seven miles out away from it all. Before sunset, you sail to and will have time to explore an uninhabited beach, swim and relax, then dine under the stars as our crew tends to your wishes.

Day 3-The next morning after your breakfast watching the birds and wildlife, we depart toward Key West with more exploration along the way. You will arrive refreshed and ready to relax at the docks with plenty of time to finish up your shopping and then after your last evening at the docks among other sailing vessels and yachts, feel like you have experience the actual island way! Let us know if you wish to extend or customize your charter.

We are fortunate here in the American Caribbean the barrier reef knocks down the ocean waves and creates the 7-mile wide protected Hawk Channel ( where the waves are rarely higher than 2-3 ft) between the Keys and the reef. On top of that there is a natural river that runs from the Atlantic Ocean to the Gulf of Mexico with dolphins and turtles usually at play. West of Key West there are many uninhabited islands to enjoy their natural beauty. Our favorite has a crescent shaped beach. There is a safe lagoon to anchor in for the night. The stars are amazing from there.

Design your own custom Sampler Package or choose from our Standard Sampler package which is: 3 nights on board; first night at the dock, Noon the next day depart with food, captain, & mate for 24 hours to return the third day noon to enjoy your third night at the dock.

To date this is our most popular charter. The blend of dockside living and being on the water allows many couples and/or families to determine if this is a way to go for them again or to retire on a boat.

Key West Sampler Pricing


$1660 3-day package


$1860 3-day package


$1860 3-day package

Key West Sampler pricing is based on double occupancy; an additional charge of $300 per additional person 14 years and older, per package will apply; 4 persons preferred but for families up to 6 passenger maximum per boat.

Book your lodging and vacation activity today! 305-304-4911

Key West Sailing Excursions

A beautiful sunset with solar reflection from one of our longer trips up to Boca Grande

This is a specialty of ours. Our well-trained captains and mates look forward to our excursion sailing trips. Our sail-boats are chosen for their sailing ability and comfort underway. Our boats are heavy, over 12 tons, not like a bobbing fishing boat. They move smoothly through the water as if they are part of the sea. Nearly 60 foot high masks guide the wind to shape these sailing wings.

The Key West area offers a variety of choices and directions to sail. This is why Key West was chosen for our base of operations. Up the Keys you get the choice of sailing out only to the East into the Atlantic.

Boca Grande uninhabited island private sailing vacation charter

Key West is often said to be at the end of the rainbow; being located at the end of the Island chain our customers get to choose from all 4 directions; as well as 4 bodies of water; The Atlantic, Hawk Channel, Northwest Channel, and the Gulf of Mexico. There are safe, calm anchorages that each offers a different flavor.

Our first mate Brenda taking a relaxing stroll along the beach on the unihabited island of Boca Grande

It is not unusual to have couples or a family charter one or even all three of our boats, for 3 days to a week for a first class adventure away from it all. After over 20 years at this location we know the best spots to suit the wishes of our charter clients. Join in the sailing and take the helm or lay back and read a book. There are no canned routes, the captain will ask you what you would like to do next and give you the variety before you as it relates to wind direction. Each excursion 24 hours away from the docks has no limit how many traveling days and nights, variety of daily choices on types of accent as listed (under Sailing Getaway options) or make up your type of vacation trip with all your meals included with non-alcohol beverages, BYOB, fuel, crew with captain and mate, the whole boat for your group or couple.

Ask about sailing training; either for your knowledge casually as a simple introduction, or with a certified sailing captain and learn the intricacies of the boating life and its requirements. Choose to relax instead and let the crew take good care of all your wishes. The menu is designed with you help in advance by email and within two weeks of your excursion the first mate has an idea of your palate.

Breath taking reef snorkel dives, take the helm, pull the sails, drop a line in the water with your special somebody or perfect for a family and great for company team building to get away from it all off the docks and away from the crowds with just the American tropics fish, flora and fauna.

Private charter to Bahamas, nice shot of beach Beach in the Bahamas, long distance private sailing charter.

Expert international licensed captains with thousands of at sea miles under their keels await your challenge to a bigger adventure; our favorite is the Bahamas. A minimum of 5 days, 10 recommended is a summer treat. This is normal for Floridians to do, head to the Bahamas for an island adventure.

The boats are equipped for long distance travel or local island hopping. Tell us your schedule and your wishes and we will design the custom package for you for your review. Share how much you are acquainted with sailing; are you are a seasoned sailor or a novice who needs some basic guidance; select the Sailing Excursion Charter and we will take care to do the rest for you.

Key West Sailing Excursion Pricing


$1160 per 24-hour period


$1295 per 24-hour period


$1295 per 24-hour period

24-hour excursion rates are based on double occupancy; An additional fee of $150 per additional person 14 years and older, per 24-hour block will apply; please call for family rates; 2-4 persons preferred, 6 passenger maximum; longer excursions will be discounted accordingly.

To cruise the American Caribbean, the Bahamas, or Island-hop with us, call 305-304-4911

Key West Snorkel Charter

Underwater photo of girl snorkeling with conch shell.

Enjoy our local reefs after you sail 7 miles out from Key West to where the Keys and reefs meet the edge of the Ocean Gulf Stream teeming with colorful life. Snorkel among the myriad of corals and varieties of wildly colored fish. Our crew have learned the routes and help you select a beautiful reef trip that work best when the tides and wind are going a specific direction and will guide you on your snorkeling experience. Having a private and custom charter makes all the difference. Snorkel gear will be provided. Confer with your captain and mate the best reef that day. You are in charge of how you want to spend your time and where not like the 'canned' commercial boats on a tight schedule to the same place every time. Our Company sails with flexible scheduling for up to six people, with all gear on board. For stand-alone day only charters, expect a fresh deli sandwich lunch and non-alcoholic drinks BYOB when you are planning a day sail, 4 hours or a half day, six hours for an extended day or full day of eight hours. Commandeer the vessel, ask the captain for the helm, feel the breeze, the boats gentle movement, sails breathing and the feel of the sea under your boat. The captain will stand beside you and let your friends or family pull the sails up. Take advantage of this great photography opportunity that will capture your pirate renaissance moments. Argh me mateys! The captains and mates know the best places to go and have an excellent safety record. Our sail-boats are classics, real sailboats. They are built heavy and ride the water well for a smooth, comfortable experience. We will work with you as to the departure time. Once you are comfortable with your snorkel gear, you are able to immerse yourself into a world of curious sea creatures that may come close to you wondering what species you are. Many times sea turtles have joined our snorkeling and fish come up as if to greet you. The purity and quality at our reefs has been steadily improved over the years. Reef Relief Programs in the Florida Keys have protected the growth and improvement of our barrier reefs. Please do not touch the reefs nor swim into the freshly grown new reefs. Enjoy swimming with large healthy parrot fish, see light rainbow or midnight blue parrot fish, yellow friendly snapper, yellow and black striped sergeant majors, blue tang, silvery barracuda, grouper, and ever a few small nurse or white tip sharks who are only interested in the reef fish may be a part of your time at the reefs. No worries! We are not part of their food chain, no seals here. Wave action is minimal and you and the sea creatures may readily see each other and you will be able to tell your friends and family that you could see the inhabitants of a pollution free reef with the wondrous experience up close and personal with creatures that are not threatened by your presence. The magical mother ocean reveals mysteries of the deep in less than 30 feet. After you have been amazed and before you get tired your crew will assist you back into your boat, and have lunch sandwiches or wraps ready for you with sodas, water or other beverages (bring your beer, wine, champagne and good spirits.)

Tell us what type of experience you wish:

Snorkelers enjoying a day in the waters

Add fishing to your sailing charter time catch and cook your own feast. A FL Fishing license is required, call ahead for your fishing license at: 888-Fish-Flo

Dolphin watching in the wild; we know places where they like to play. Bird watching on a protected island and beach combing. Reef exploration and discussion of our local wild life. Sailing with the captain and mate learn the basic signs and routes introduction of navigation basics. Learn how to reef the main and learn weather while on a sailboat (Ask about our in depth training.) Based on what you would like to learn about, experience or talk about, tell us what kind of trip you would like and we can gauge what your time line should be. There are other charter boats and other companies that do offer a less personal experience. We are able to custom design your time sailing as if you own the sailboat. Tell us what you feel that you wish to find in the many destinations available to you through our thoroughly trained crew. The big boats can take you with a basic trip to a nearby reef with 40 or more people, yet we are with you all the way.

Lunch with water and Sodas / Gatorade, juice etc. provided times flexible; from 9 am to 8 pm Bring a cover up plus sunscreen with a hat, the sun is closer to you here. Towels; can be provided as needed, feel free to ask the first mate to get one out of the dock box, or if you have your own favorite big beach towel ok to bring it too. We have a lot of lounging space on our decks on all three boats. BYOB non-alcohol drinks provided and iced down, bring your own wine, beer, champagne libations.

Key West Day Sailing Prices

4-hour Daytime Sail


4-hour Daytime Sail with Sunset


8-hour Reef or Island-hop Sail


For a great vacation activity while staying in Key West, call and book today! 305-304-4911

Speciality Sails:

For any special remembrance, it is a pleasure to help you design individual charters to your heart's or your sweetheart's content; any flower or food choices; cakes, cheese & fruit trays, snacks and drinks, and more! Call us for questions or recommendations. From proposals, restating vows, or commitment vows, birthdays, anniversaries, even burials at sea, let us guide you and prices will vary depending on what is available and what you wish to add to a basic typical day time 4-6-8 hour sailing trip. Your imagination should be allowed to extend the ideas.

Call Us For Prices 305-304-4911

Weddings at Sea:

Bride and Groom after exchanging vows on our wedding charter.

Traditionally at sunset (times vary throughout the year call and we can help you plan). Flowers for the bride, boutonniere for the groom, food tray, tropical designed wedding cake; Weddings for up to 6 persons on board plus captain and mate start at a comfortable low cost for approximately three hours with room enough to bring two or four other guests, with your captain and mate provided and notary or Reverend included, usually one will perform your sea themed vows or help with your own personally written vows. Add more sailing time depending on scheduling, prices according to current rates and what you wish including adding overnight at the docks additional meals on your own. Maybe you want to get away from it all with an excursion then staying at anchor under the tropical night sky. See current a la carte pricing and time of the year.

Wedding/Honeymoon Prices

Sunset Wedding Package


3-day Wedding/Honeymoon Package


Call Us to book your dream wedding! 305-304-4911

Sailing Lessons:

Call 305-304-4911 for pricing and availability. Learn and be certified as a sailor.

International Traveling:

Two of our guests taking shore leave on a dingy in the Bahamas on vacation.

Sail to the Bahamas or out to the edge of the Gulf-stream and even Mexico; we can take you there. Plan a few days to a couple of weeks, your choice for a total destination sailing charter. You can choose to sail around the Florida Keys from Key West to uninhabited islands towards Cuba or to Key Largo, welcome a plethora of places to experience. Pricing according to what your charter goals are. Base price starts with excursion per day pricing, discounted by the length of your trip and the number of people, or when visiting a foreign country estimate international fees special rates will vary according to where and when you are staying. Should you desire old world style, courteous crew, knowledgeable sail boat charters make this your Key West vacation choice.

Base Pricing

Questions often asked:

How to prepare for staying aboard charter packages? On Stay/Sail charters most of our guest's time will be spent at the docks with a few hours of sunset sailing. 24 Hours or more away from dock during Excursions or Key West Samplers

How do I pack?

Soft luggage best for storage, please avoid hard luggage. It will overpower your space on a boat. Pack light it's casual everywhere! Depending on your stay, this list is based on a 3 or 4 day stay. Also, we know that you will probably want to leave room in your suitcase for our tempting shops that offer unique Key West apparel with a tropical twist. No matter what time of the year you visit Key West, summer wear is always available. When staying at the docks, pack flip flops or sandals, and you can buy some here in town, then consider a pair of good walking shoes, and if you don’t have them, nearby shops are fun to get fun Key West outerwear. Since you are three blocks from downtown Key West, you can walk to most of the attractions you have heard about or seen on television specials about Key West. If planning long treks sailing mostly away from the docks, you may want only one pair of shoes for when you catch the plane home. Bring two bathing suits needed daily one to wear and one to dry out for the next day. Two pairs of shorts, two tops, ladies enjoy wraps or cover up cotton dresses, men want to remember they can use a light weight cotton shirt to fend off the sun, 1 or 2 hats, sunscreen, some kind of light jacket and lightweight jogging type pants as it gets cooler at nights, a small toiletries personal bag. Snorkeling and fishing gear is provided; get fitted by your first mate before leaving the docks. We provide towels and make the beds with linens and pillows with beds made up when you arrive. If you option to bring a straightening hair iron or hair dryer please use at the marina shower house. (Why? our boat electric system will overload; it's really best to plan wash and air-dry hair or ladies here just braid or put hair in a bun, as in tropical climate as these tools may be a lesson in futility. You may find it's less stressful and just plan to be comfortable with informal).

What can you expect for menu when you are staying on board?

If you stay at the docks, meals are on your own; you will want to walk to a number of night hot spots, fun lunch and delicious dinner destinations and discover the museums and sunset nightly festival, submerge yourself into street performances and frequent arts festivals or find the music throughout downtown that may be happening. For when you are planning to be overnight on anchor and spend each of your 24 hours sailing normally counted daily as noon to noon sailing, swimming, exploring, meals are provided.

How much is a gratuity?

Usually 15-20% value of the time that you are out sailing, we can help, but it's up to you. Please remember that your captain and mate want to earn your approval and are proud of their work. Finally, bring your adventurous spirit and enjoy the historic seaport while recapturing the old Key West days filled with tales from the sea, live music at old haunts famous writers may have gone to, the nightly sunset arts festival, numerous art galleries or stumble upon a street festival while here.

Call Us To Book Today: 305-304-4911

Please review our payment, booking, and cancellation policy

Trusted charters since 1995 Key West Sailing Adventure, Inc.

See Trip Advisor for our strong rating by our clients.

Sail Ho!