sailboat charters in the florida keys

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Sail the Florida Keys

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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. 

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Private Liveaboard Classes

Florida keys sailing, come sail with us.

Proud Member of the ASA

At Florida Keys Sailing our specialty is: Private Live Aboard Sailing Classes and Sailing Vacations with just you and your spouse or friends. “Learn to Sail” or take an Advanced Class to develop your skills. Qualified sailors can Charter our boats. A Captain will happily take you and your family on a Day Sailing Trip if you need one. Many sailing classes offered elsewhere crowd you on a boat with a group of total strangers.

At Florida Keys Sailing ALL of our Sailing Classes, Day Sailing Trips, and Private Charters are exactly that…PRIVATE.

No one else except YOUR Party is ever on-board. This means you will learn more by having more time DOING, not WATCHING someone else sail. Dollar for dollar you will find more VALUE in taking your Sailing Courses at Florida Keys Sailing.

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Fun on the Waves

Our Classes

To learn more about the liveaboard classes we offer, visit our classes page

2 DAY BASIC FUNDAMENTALS OF SAILING

Designed for beginners who want the best introduction to the exciting sport of sailing. Students will receive a good understanding of all the “Basic Fundamentals of Sailing”. They will leave as very competent Crew Members.

3 DAY BASIC KEELBOAT “LEARN TO SAIL CLASS”

Beginner students will learn to responsibly be the Skipper of a Day Sailing Keelboat in familiar waters in moderate wind and sea conditions. Classes available are year round on demand based on your travel plans.

5 DAY BASIC COASTAL CRUISING OR 101 & 103

Students will learn to responsibly skipper and crew an auxiliary powered cruising sailboat during daylight hours within sight of land in moderate wind conditions. This Private Live Aboard Class is taught aboard our Catalina 30' or Irwin 34 Offered all year on demand based on your travel plans.

5 DAY BAREBOAT CRUISING OR 103 & 104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock

3/1 DAY ADVANCED COASTAL CRUISING OR 106

Cruise a sailboat during nighttime hours in most wind and sea conditions. A Private Live Aboard Class is held aboard our Catalina 30 or Irwin 34. Offered all year on demand based on your travel plans. 3 Days and 3 Nights…Privately Living Aboard

7 DAY BAREBOAT CRUISING OR 101, 103 &104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34 This is the Class the Bareboat Charter Companies want you to have. Offered all year long on demand based on your travel plans. 7 Days and 6 Nights…Privately Living Aboard at our Dock

3 DAY FAST TACK TO CRUISING ASA 101 & 103

It’s the fastest and least expensive way to get the first 2 – ASA Certifications. Both combined into a 3 Day / 2 Night Live aboard Class. Prior sailing experience before enrolling is advised. Only $2,039 per student! And better yet…a second student enrolls for FREE!

5 - DAY FAST TACK TO BAREBOAT CRUISING ASA 101, 103 & 104

It’s the fastest and least expensive way to get these 3 - ASA Certifications. All 3 are combined into a 5 Day / 4 Night – Live aboard Class. Prior sailing experience before enrolling is advised. Only $3,599 per student! And better yet…a second student enrolls for FREE!

Testimonials

Daysailing & charters, we offer both daysailing and charters, click below to learn more.

• SAILING LOCATION: Keys Fisheries & Marina 35th St Gulfside, MM 49 Marathon, FL 33050
• By Mail: Florida Keys Sailing 5171 Overseas Hwy #504407 Marathon, FL 33050
• By E-Mail: [email protected]
• By Telephone: 305-619-0140
• Marathon Chamber of Commerce
• Get Knotted - Animated Knots
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Copyright© 2020 Florida Keys Sailing™, LLC

 Key West & Marathon, Florida

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

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

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

Florida Yachts Charters is pleased to offer a curated fleet of yachts tailored to the best sailing and cruising experiences in the Florida Keys and Key West. Whether you are a seasoned bareboat charterer, you are interested in learning more about sailing through ASA sailing instruction, or you just want the luxury of a crewed charter we have a yacht to fit your group size and requirements. Each yacht is well maintained and appointed with all the amenities needed to make your multi day sailing vacation a breeze. Welcome aboard!

Sailing Monohull

Sailing catamaran.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

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Bloody Pirate

• Information

The Bloody Pirate is a beautiful schooner sailboat in the luxurious Florida Keys. She is named after the famous Code Rum cocktail drink. Enjoy an exciting Keys sailing adventure and watch us hoist her red sails on a true tall ship.. She can accommodate intimate private parties or large groups up to 38 people for day charters or 24 overnight. With her classic lines and open interior you'll feel right at home. Her professional crew will enable you enjoy a relaxing cruise or you may try a real hands-on sailing experience. She is the perfect vessel to take you to the abundance of tropical reefs in the Florida Keys to snorkel and explore. She is particularly suited to large group charters.

PROVISIONING SERVICE

Calypso sailing offers a provisioning service to help get your charter off to a great start. With a little prior organization you can arrive to a vessel that is fully provisioned to your own tastes. We can provide food shopping lists, food and cocktail menus to  ensure that all your necessary and favorite items are all onboard and ready for your charter. We are happy to arrange any of your vacation essentials for you so you don't have to waste valuable vacation time shopping. 

Feel free to contact us about shipping some items to us ahead of time also we will make sure they are waiting onboard for you.

Please call for all departure times or for further information.

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“If one advances confidently in the direction of his dreams,

And endeavors to live the life he has imagined,, he will meet with success unexpected in common hours.”, henry david thoreau.

Sail On’s cruising grounds span the Florida Keys from Miami and Biscayne Bay to Key West and the Dry Tortugas. Periodically, Sail On can be found in the protected waters of Tampa Bay and in satellite bases in the Abacos.

Captain John  has sailed the Caribbean for more than two decades.

Our 2019 Season

Key west thanksgiving.

Sail On relocated for the 2019 holidays, returning Thanksgiving week to one of her favorite spots: Key West. It was a great way to bring a busy sailing season to a close.

At the dock

Shrimp boats

Prepping to depart

At the Stock Island dock

Ahead to the horizon

Thanksgiving 2019 crew

Parker at the wheel

Portrait of Ed

LGC onboard

2017 sailing season.

Follow Our Adventures

Florida Keys

Some of the most unique vacation destinations in the world can be found in unexpected places – such as the Florida Keys. Located just off the coast of South Florida, these islands have a relaxed feeling, stunning tropical scenery, and exotic wildlife; yet they are all located a relatively short distance from cosmopolitan Miami and the excitement of South Beach, where the journey begins.

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• Newfound Harbour

Miami is South Florida’s playground, and for good reason – there is no where like South Beach to both enjoy the sun, sand, and surf by day, and live it up by night in the area’s many exclusive night clubs and restaurants. Whether you want to dance all night and enjoy premium bottle service or simply have a wonderful meal by the water, launching in miami ensures that you will start your voyage off in the most exciting way possible.

Visiting during one of the many major annual events that occur in Miami (including Art Basel, the South Beach Wine & Food Festival, the Orange Bowl, and more) will make your trip even more outstanding.

As the northernmost and largest island in the Florida Keys, Elliot Key was once used a refuge for pirates and today it is home to Biscayne National Park, with its lush vegetation and amazing beaches that offer both remarkable solitude and spectacular vistas – along with a variety of exotic birds and butterflies. You can also explore the island by kayak – there are many hidden lagoons, mangrove-covered shorelines, and winding creeks to discover. What’s more, you can enjoy your own catch for dinner after a day of capturing fish, lobster, or crab.

Key Largo is considered the “Diving Capital of the World”, with plenty of scuba diving, snorkeling, and sport-fishing options for avid enthusiasts – what’s more, it is located near the Everglades, allowing for easy access for kayaking and eco-tourism as well. It is the home of the only living coral barrier reef in the continental United States, and enjoys more than three thousand hours of sunshine per year, making it perhaps the quintessential island vacation destination.

Named after the original settlers’ boat the “Island Home” and now nicknamed the “Village of the Islands”, Islamorada is home to many notable residents (including Major League Baseball players Ted Williams and Miguel Cabera as well as actor Gene Hackman), this is one of the more serene island destinations in the Florida Keys as well as one of the world’s premier fishing destinations. Luxury resorts, shops, and art galleries are part of the Islamorada scene, but there are plenty of beaches that offer more solitude.

With less than two hundred residents, Duck Key is perhaps the closest version of a deserted island that’s still easily accessible from the contiguous U.S.  With world class fishing and sandy beaches, the island is also home to a luxurious spa and offers the opportunity for visitors to swim with dolphins.

Newfound Harbour not only offers spectacular scenery, it is home to the Florida Keys Sanctuary preservation area, which is partially located within the Coupon Bight Aquatic Preserve. The amazing sea life that visitors to the island will enjoy includes star corals and giant brain corals – perfect for amateur or inexperienced divers since these are located within in depths of 18 feet or less. Angelfish, butterflyfish, surgeonfish, damsels, wrasses, grunts, snappers, and parrotfish swim alongside the occasional grouper, along with many other types of fish that you’ll find colorful, striking, and unusual.

Along with some of the most interesting coral reefs in the world, Newfound Harbour is home to a sheltered tropical lagoon that serves as an oasis for a wide range of wildlife, including the tiny Florida Key deer, wading birds, and sea turtles.

Taking a little time to leave it all behind in Key West may be the ultimate form of relaxation – particularly if you happen to visit during one of the island’s most distinctive festivals (The annual Fantasy Fest held in October is the most famous). There’s excellent opportunities for scuba diving and snorkeling around the coral reefs and shipwrecks in the nearby waters, including the recently sunk USNS Gen. Hoyt S. Vandenberg, which created an artificial reef.

However, the island’s unique National Parks and wildlife refuges are perhaps the most interesting (at least for nature buffs), and the nightlife in general is not to be missed, with a variety of options that range from casual tropical dives to trendy nightclubs. All in all, Key West is the perfect culmination to your customized trip through the Florida Keys.

Sailing the Florida Keys may possibly be the very best way to unwind and explore a corner of the United States that hardly resembles anywhere else in the country – or the world, for that matter. And there’s no better way to experience this special part of the world than on your own private yacht.

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The Florida Keys

Explore the southeast Florida coast and the renowned Florida Keys.  Start by exploring Key West, the most southern point in the continental USA. Take in the former residence of Ernest Hemingway, enjoy the sunset celebrations in Mallory Square, visit Smathers Beach and tour the Key West Lighthouse.  When planning your sail from Key West, make time for Key Biscayne with its breathtaking Bill Baggs State Park. Biscayne Bay offers calm cruising and Elliot Key is a popular anchorage if you want to snorkel, swim or explore.  You will be spoilt for choice when it comes to the 800 islands that make up the Florida Keys, which can offer everything if you love being out on the water, such as watersports, fishing, and incredible sunsets. You can stop by Key Largo, Islamorada and Marathon to name just a few.  At Key Largo you can explore the living barrier reef before heading to Islamorada with its six keys bursting with history and known for its fishing.  

If you worry you won’t have time to see everything you want to, you can also do a one-way charter by starting or ending your charter in Key Largo, Marathon, Key West, or Miami.  Miami offers the South Beach strip on Ocean Drive, the famous long stretch of white sand with a backdrop of Art Deco architecture and a vibrant atmosphere. There are plenty of hip restaurants and great shopping.  Miami has become a thriving arts scene too with art museums, private art collections open to the public and an annual contemporary art fair.  For those seeking a longer sail, you can head to the Dry Tortugas National Park and the uninhabited Marquesas coral reef islands. For those looking for a more challenging sail, you can head out east to Bimini in the Bahamas.

Sample Itinerary

Day 1 Key West: Board and overnight in the marina or anchor in front of Key West.

Day 2 Key West – Bahia Honda Key: Make the most of the watersports and anchor at Rodriguez Key or Tavernier Key. If you’re looking for facilities, try the Pilot House Marina.

Day 3 Bahia Honda Key – Indian Key: Explore the Indian Key State Park – a great opportunity to paddleboard or kayak. Head to the south-west of Indian Key to overnight.

Day 4 India Key – Key Largo Reef: Snorkel with the colorful marine life – we recommend Molasses Reef, Conch Reef and French Reef in the state park. Explore Key Largo and anchor nearby or in the marina.

Day 5 Key Largo Reef – Long Key: Go ashore for a hike in Long Key State Park and see the wildlife, try a spot of fishing or swim and snorkel. We advise anchoring on the northwest of the island.

Day 6 Long Key – Marathon: Enjoy browsing the shops to find souvenirs or dine locally. Marathon has a welcoming, upmarket atmosphere which is perfect for a day out.

Day 7 Marathon – Key West: Watch the sunset in Mallory Square – it’s a must-see and one of our favorite things to do on a Key West yacht charter. Treat yourself to a delicious meal in one of the many restaurants.

Day 8 – Key West: Head back to the marina after a leisurly morning.

½ - Full Day Sail, Snorkel, Kayak, Sunsets

2 to 6 individual passengers or single groups up to 12. Laid back relaxed fun atmosphere. Enjoy our Captained sailing/ snorkeling or sunset Sails, both Bayside & Oceanside. Let 30 years of experience on the reefs and waters around Key Largo set you free to discover. Enjoy the beauty of the Florida Keys.

Captain Only Charters

Included is a luxury, well-equipped catamaran or monohull with an experienced and professional Captain in charge of the boat and helm. Sit back with a chilled cocktail and experience an unforgettable dream vacation in the beautiful Florida Keys.

Bareboat Charters

Included Catalina 22’ to a performance ORA design 36’ C&C or Gemini 34’ catamaran, our boats are well-equipped for their chosen usage. Enjoy the freedom of a self-captained vacation. Explore and enjoy sailing in calm, turquoise waters of the Florida Keys.

Own-er-ship in the Florida Keys. What are the benefits:  Tropical, US Waters, 1000’s of miles of shore line, Second Largest Coral Reef in the world, Quick & Easy Access.

Learn to Sail

Learn to Sail or advance your sailing in The Florida Keys. We have an in-house sailing endorsement that teaches you to sail a 22 ft Catalina 22 sailboat or we have the advanced ASA classes from Learn to sail ASA 101 to ASA 120. Why sail in the Florida Keys?

Cottage & Sailboat

Enjoy the beauty of the Florida Keys. Accommodations + Free Sailboats, Kayaks, Canoes, Paddle boards, Fishing/Snorkeling gear and more. All included in a Laid back relaxed fun atmosphere. On the Bayside of Key Largo. Let years of experience around Key Largo Florida set you on a path of discover.

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

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FOCUS | From US$ 150,000/wk

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Florida Keys Yacht Charter

Often considered America 's Caribbean Islands the Florida Keys yacht charter offers spectacular locations to explore.

You will often read references to a 'jade necklace' or a 'string of pearls' in descriptions of the many (800+) islands that stretch off into the sea. The Keys have become increasingly busy over the last few years with an increase in cruise ship and other tourism. The keys feature plenty of energy ashore, but to get away into the quieter areas a charter yacht is the only way to go.

Photos: 1. A diver explores the coral reef in the Florida Keys National Marine Sanctuary off Key Largo - The reef system in the Keys is the only contiguous coral barrier reef in North America - Photo by Bob Care-Florida Keys News Bureau; 2. A Florida Keys fishing guide positions his angler to cast for a bonefish off Key Largo- Photo by Bob Krist-Florida Keys News Bureau; 3. Sunset in Key Largo- Florida Keys- paints a pretty picture at the Kona Kai Resort -Photo by Bob Krist-Florida Keys News Bureau

The first Key to come across on your cruise south will be Key Largo . Over the years Key Largo has become a busy weekender retreat from the mainland. As you sail further down though the Keys you will finally come to the last one, Key West .

The Florida Keys are sheltered by the only living coral reef in the United States. The Keys are well known to yacht charterers for the spectacular scuba diving and snorkelling, kayaking and eco-tours, dolphin watching, island hoping and fishing.

The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter.

The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all the best areas within the Florida Keys.

Key West Yacht Charter

Key West has the ideal year round climate for yacht charter. Key West is a very unique town being the southernmost US city where history and tradition meets natural beauty and serenity. This city has real estate titles that date back to the King of Spain! Within walking distance from the historic Seaport District you will find palm-lined streets, tropical gardens, Ernest Hemingway's home, fine shops, art galleries, quaint restaurants and cafes. You can walk in the footsteps of Thomas Edison, Lou Gehrig, Harry Truman, and Tennessee Williams. You will also discover lively bars and pubs along with street musicians, jugglers, mimes and artists.

It is not unusual for charter guests to day sail their charter yachts using Key West as a base. They will sail and explore the keys during the day, utilising the restful anchorages, and then return to the first class marinas at night to experience Key West's nighttime entertainment. Remember to radio ahead to reserve marina space, as Key West is a busy part of the Florida Keys.

Below is a selection of fabulous Florida Keys charter yachts - please, contact us for additional vessels and more information here .

• Florida Keys Charter Itinerary
• Browse Florida Keys Charter Yachts
• Luxury Motor Yachts for Charter in Florida Keys
• Luxury Sailing Yachts for Charter in Florida Keys
• Luxury Catamarans for Charter in Florida Keys
• Florida Keys Yacht News

Florida Keys Yacht Charter Enquiry

"I have just emailed your post charter feedback to you. It doesn't say nearly enough about how well and hard you worked on this deal. I am a retired commercial real estate broker who understands the importance of the deal-maker in the deal. You are a deal maker of the first order." E. G - chartered in Florida Keys.

Yachting Destinations Near the Florida Keys

In close proximity to the Florida Keys are a number of exciting sailing destination.

New England

Napa Valley

Yachts for charter in the florida keys, queen miri | from eur€ 1,125,000/wk.

KENSHO | From EUR€ 850,000/wk

WAYFINDER | From US$ 375,000/wk

MARIA | From US$ 230,000/wk

LADY ELAINE | From US$ 225,000/wk

GIGI | From US$ 225,000/wk

TCB | From US$ 215,000/wk

MYSORAH | From US$ 200,000/wk

ASPEN ALTERNATIVE | From US$ 199,000/wk

FAM | From US$ 195,000/wk

GLORY | From US$ 179,000/wk

ZOOM ZOOM ZOOM | From US$ 175,000/wk

AVALON | From US$ 155,000/wk

AQUASITION | From US$ 150,000/wk

RELENTLESS | From US$ 150,000/wk

PERSISTENCE | From US$ 140,000/wk

ANTELOPE IV | From US$ 140,000/wk

CLAIRE | From US$ 139,500/wk

ICE 5 | From US$ 135,000/wk

Florida Yacht News

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Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Lucky you... You just found Paradise!

Come sail away with the crew of troika ii , chart your own course... florida keys / bahamas, four-hour half-day rate $595 . book before noon this friday and receive a reduced rate of $525.

One week Sailboat Charters should not cost you an arm and a leg !! A Sailboat Charter is a great way to spend your vacation. Sailboat Charters of Miami specializes in Sailboat charter vacations. You don't have to spend a fortune on Florida vacations to have the time of your life. For just $1240(no kidding), you can escape to a tropical island paradise aboard your own crewed yacht!  If you are the type that enjoys pitching in a little, you can enjoy a Bareboat Charter, (the captain does all the hard stuff) . Don't compromise yourself any longer.... Cast-Off your worries and chart a different course ! Cruising vacations are relaxing vacations.  Take a Sailboat Charter, and you will always remember how fun and relaxing it was. We have Sailboat Charters to the Florida Keys, Sailing Vacations to the Bahamas. This is one of the best ways to celebrate spring break! We have the very best Spring Break Sailboat Charter vacation packages that you can find CHECK OUT THE STUDENT SPRING BREAK SAIL BOAT CHARTERS ON THE Spring Break Page! If you are looking for a Sailboat Charter in the Florida Keys, you have just found the Sailboat Charter company to do it with. Sailboat cruising is one of the most relaxing ways to spend your vacation.

Have you always had the dream of spending an intimate Honeymoon out away from it all? We have the answer. A honeymoon sailboat charter! Think of just the two of you, watching the sun go down over the bow, a warm breeze blowing, a nice cool drink in your hand, and no worries in the world. A honeymoon sailboat vacation is just what you want. Click here to check out the honeymoon sailboat charter. It is truly a Honeymooners dream trip! Our honeymoon sailboat vacation, is the best deal you can find on a truly unforgettable honeymoon! It is all inclusive, so no hidden fees or extras.

Charter Smarter... Sailboat Cruising in the Florida Keys And Bahamas is a phone call away !

Where are we located.

Sailing Charters in Florida never gets easier than this. Our Luxurious all teakwood sailing clipper is home based in the new Dinner Key Marina

in the heart of 'hip' Coconut Grove, Florida just a few miles south of Miami Beach and South Beach. This location is minutes from the airport, and is a convenient 'jumping off point' for Sailing Charters to the Florida Keys or across the Gulf Stream to The Bimini Island Chain in the Bahamas. From our marina you are minutes from sailing Bay and the fascinating coral reefs and sea gardens of John Pennekamp State Park. Summer or Winter. Florida Keys Sailing offers fun, protected-from-heavy-weather sailing. http://www.nps.gov/bisc -->

What Can we Do For You?

Charter your own Skippered Classic Clipper..... 46 feet of Traditional Elegance and Luxury For... Family Sailing Charters, Cocktail Parties, Private Day Charters, Special Occasions, Anniversaries, Birthdays, Sailing Charters in the Bahamas, Sailing Charters in the Florida Keys, Weddings at Sea and.. All Custom Tailored to your exact requirements. We want to make your Florida Sailing occasion an experience that you will cherish and talk about for years to come !! Come vacation amid some of the clearest waters and most spectacular cays and lagoons in the world, come sail with the crew of TROIKA II. Thrill to an exhilarating reach into paradise, troll for Mahi Mahi, grouper and mackerel, anchor in secluded lagoons, snorkel and explore our vast world-famous underwater preserves teaming with exotic marine life. Discover mysterious blue holes, caves or swim with playful dolphins. At days end, sit back and relax with your favorite 'sundowner cocktail'... relish the crimson sun dip behind magnificent deep blue seas..... savor a scrumptious candle lit dinner under glittering night skies.

The bottom line is we offer the best yacht in the business, best guest accommodation's, (check out the specifications page ), Best meal plan (check out the menus page ), the most experienced and personable crew (check out Captain David's page ), and a more varied cruising area for the price! Florida Yacht Charters are FUN and SAFE! We do not raise our rates during high season... EVER ! Cruising Kitty Limited? Check out the budget page , and the Skippered Bareboat page in the Packages Section. For more information E-mail us ,

"For Many years now we have enjoyed introducing people to the joys and challenges of crewed sailing charters and the wonders of our sub-tropical paradise. We enjoy sharing with our guests our many years of experience running 'the big boats'. Safety seamanship, rules navigation, piloting, handling, anchoring, knots, terminology, provisioning, food storage, onboard cooking, special recipes, scuba diving and snorkeling, spear and line fishing are just some of the skills and topics we'd like to share with you. We always encourage our guests to do as much or as little as they wish. Our primary concern however, is to make your hard earned vacation enjoyable, informative, and above all " safe." We also offer clothing optional Sailing Charters, along with Gay Sailing Charters. Yup mates... all are welcome! Sailboat Charters strives to provide the best atmosphere for a most relaxing sailing vacation for up to 6 passengers with a roomy 46 foot sailboat and all the amenities. Your pleasure is our number one goal ! Sailboat Charters are truly the best, and most relaxing way to spend your vacation. A sailing vacation is an unforgettable experience!

Company Profile

Captain David Sullivan U.S.C.G. License #733129 issued in 1988 - Unlimited Master's License, 100 Ton for steam, motor, or auxiliary sail vessels.

Captain David Sullivan has the education, experience and personality to provide the safe sailing adventure you'll cherish and talk about for years to come. David was born and raised in 'The Old Whaling Capital Of The World', New Bedford, Massachusetts, on Cape Cod. He has been sailing out of Miami Florida for the last 20 years. 

Contact Information

 Call or e-mail now for more information. Book early to ensure your charter boat will be available when you are. Call Now ! Telephone (305) 772-4221

Out of the USA Use the proper country code 011 (305) 772-4221

Postal address 2829 Bird Ave. PMB 216 Coconut Grove, Florida 33133

Electronic mail General Information: [email protected]

Webmaster: [email protected]

Captain David : [email protected]

Come for a beautiful Sailboat Charter on her! This Sailboat Charter is the Dream of a lifetime.

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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.

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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

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