Caribbean

US Virgin Islands A Learn-To-Sail Vacation

Go Sail Virgin Islands
Availability : through July 2024
101 / 103 / 104 / 106 / 114 / 118

Get your bareboat license from Go Sail Virgin Islands on a week-long, live-aboard Learn to Sail Vacation aboard a Catamaran, Trimaran, or Monohull Course in the Virgin Islands with hands-on experience, fun, and adventure with experienced local instructors.

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Abaco Island, Bahamas A Learn-To-Sail Vacation

Vagabonde Sailing Adventures
Availability : through June 2024
101 / 103 / 104 / 105 / 106 / 114

Welcome aboard the renowned ‘La Vagabonde,’ the 48 ft performance catamaran, which has captured hearts worldwide through the adventures of Elayna, Riley, and their kids on the YouTube channel ‘Sailing La Vagabonde.’ Crafted by renowned French builders Outremer, this seaworthy vessel has conquered multiple ocean crossings, proving its mettle on the high seas.

From$2,500
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Islands of Belize, Central America A Guided Flotilla

Belize Sailing Vacations
Availability : Jan / Apr / May / Jun / Jul / Nov / Dec 2024

Explore Belize’s paradise islands on your own private luxury catamaran. Learn sailing from ASA certified instructors & crew. Snorkel, kayak, and fish in crystal clear waters. Enjoy gourmet meals & exotic drinks prepared by your crew. Experience a different destination every day on this ultimate sailing vacation!

From$2,995
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Islands of Belize, Central America A Learn-To-Sail Vacation

Belize Sailing Vacations
Availability : Jan / Apr / May / Jun / Jul / Nov / Dec 2024
101 / 103 / 104 / 105 / 106 / 114

Belize’s sailing experience extends beyond the sea, offering captivating inland ventures. With BSV’s fully crewed catamarans, guests enjoy the ultimate all-inclusive charter, accessing the world’s largest living barrier reef and remote sites.

From$2,795
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BVIs and Leeward Islands, The Caribbean A Learn-To-Sail-Vacation For Young Adults

Sail Caribbean
Availability : January 2 - January 14, 2024
101 / 103 / 104

Sail Caribbean stands as a pioneering organization offering dynamic sailing programs tailored for teenagers and young adults. During this Echo live aboard course, students will embark on an unforgettable journey through the stunning British Virgin Islands and the captivating Leeward Islands, an immersive experience designed to cultivate teamwork and leadership through the art of advanced sailing.

From$5,795
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British Virgin Islands, Caribbean A Guided Flotilla

Sea Safaris Sailing School
Availability : February 24-March 2, 2024

Embark on an unforgettable adventure in the Caribbean BVIs with Sea Safari aboard a luxurious sailing catamaran. Discover the beauty of the British Virgin Islands while enjoying the spaciousness, speed, stability, and shallow draft that catamarans offer. This course is designed for both novice and experienced sailors who seek to explore the captivating waters of the Caribbean in style and comfort.

From$1,950
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BVIs, The Caribbean A Learn-To-Sail-Vacation

Puget Sound Sailing Institute
Availability : February 25 - March 3, 2024
103 / 104 / 114

The British Virgin Islands (BVIs) offer an incredible environment for learning to sail with ideal wind conditions, protected waters and beautiful scenery. With consistent trade winds nearly year-round, the BVIs are perfect for both beginners and experienced sailors alike, providing a safe and enjoyable environment to both learn the basics or refine your sailing skills.

From$4,965
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British Virgin Islands, Caribbean A Guided Flotilla

South Coast Sailing Adventures
Availability : June 6-16, 2024

Warm island sun and the lazy days of summer call for a getaway like no other! The stunning 55+ islands and cays that comprise the British Virgin Islands have two fantastic assets – accessibility and virgin beauty. Discover your “sit-back-and-relax” mode on our 11 Days and 10 Nights flotilla.

From$2,395
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Lenny Shabes Sailing Festival ~ BVIs A Guided Flotilla

American Sailing
Availability : June 16-22, 2024

Join us for a week of sailing in paradise, as our late founder Lenny Shabes, set out to teach aspiring sailors to do. To pay tribute to all Lenny has done for the world of sailing, we are calling all sailors to partake in a week of festivities ranging from sundowners to regattas in the beautiful BVI’s.

From$2,250
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Lenny Shabes Sailing Festival ~ Affiliates ~ BVIs

Availability : June 2024

To pay tribute to our founder Lenny Shabes we are calling all sailors to join us for a week of sailing in the beautiful BVI’s to enjoy festivities ranging from sundowners to regattas.

From$6,450
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Grenada, Caribbean A Learn-To-Sail Vacation

LTD Sailing
Availability : Jul / Aug / Sep 2024
101 / 103 / 104 / 106 / 111 / 114

Grenada has some of the best sailing conditions in the world, year round, thanks to the Trade Winds! LTD Sailing creates a fully immersive Cruise & Learn experience for you. We provision our trips with local food and drinks, we are expert sailors who know the area well, and more importantly we want you to love sailing as much as we do!

From$2,845
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British Virgin Islands, Caribbean A Guided Flotilla

South Coast Sailing Adventures
Availability : December 5-15, 2024

Discover why the “Christmas Winds” make December in the British Virgin Islands a sailing mecca! There is no better opportunity than our annual winter flotilla to expand your sailing skills, navigate to idyllic shores, and of course, experience the epitome of vacation perfection.

From$2,395
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