Caribbean

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.

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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.

From$3,895
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Islands of Belize, Central America A Learn-To-Sail Vacation

Belize Sailing Vacations
Availability : May - 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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AGES 18-25 | ECHO

BVI and Leeward Islands, The Caribbean A Learn-To-Sail-Vacation For Young Adults

Sail Caribbean
Availability : May 29 - June 11, 2024
101 / 103 / 104 / 105 / 106

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$5,595
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BVI, The Caribbean A Learn-To-Sail Vacation

South Coast Sailing Adventures
Availability : Jun 2024
103 / 104 / 114 / 111 / 116

Discover an unparalleled sailing adventure in the BVIs with South Coast Sailing Adventures. Refine your sailing skills and receive ASA Certifications all while explore idyllic shores and crystal-clear waters. Experience the thrill of captaining your vessel amidst a paradise of over 55 islands with ASA-certified instructors. Sail, snorkel, and soak up the sun on secluded beaches. Embrace the adventure of a lifetime.

From$2,395
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AGES 12-18 | ALPHA

British Virgin Islands, The Caribbean A Learn-To-Sail-Vacation For Teen Sailors

Sail Caribbean
Availability : Summer 2024 (Multiple Dates)
101 / 103 / 104

Sail Caribbean stands as a pioneering organization offering dynamic sailing programs tailored for teenagers and young adults. The Alpha Program offers the opportunity to sail through the stunning British Virgin Islands, earning ASA certifications while forging lifelong friendships and unforgettable memories.

From$6,095
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AGES 12-18 | BRAVO

British Virgin Islands, The Caribbean A Learn-To-Sail-Vacation For Teen Sailors

Sail Caribbean
Availability : Summer 2024 (Multiple Dates)
101 / 103 / 104

Sail Caribbean is a visionary in offering transformative experiences for teens and young adults, blending sailing expertise, cultural immersion, and personal growth. The Bravo Program is a 21-day immersion into boat life, offering the opportunity to master sailing skills while exploring the BVI. Students can become seasoned mariners with optional ASA certification courses while embarking on a transformative journey.

From$7,495
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AGES 11-12 | TANGO

British Virgin Islands, The Caribbean A Learn-To-Sail-Vacation For Teen Sailors

Sail Caribbean
Availability : Summer 2024 (Multiple Dates)
101 / 103 / 104

Sail Caribbean stands as a pioneering organization offering dynamic sailing programs tailored for teenagers and young adults. The Alpha Program offers the opportunity to sail through the stunning British Virgin Islands, earning ASA certifications while forging lifelong friendships and unforgettable memories.

From$6,095
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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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INVITE ONLY

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$1,250
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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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Islands of Belize, Central America A Guided Flotilla

Belize Sailing Vacations
Availability : Jun - 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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AGES 12-18 | DELTA

BVI and Leeward Islands, The Caribbean A Learn-To-Sail-Vacation For Teen Sailors

Sail Caribbean
Availability : Jun 17 - Jul 13 & Jul 15 - Aug 1
101 / 103 / 104 / 105 / 106

Sail Caribbean stands as a pioneering organization offering dynamic sailing programs tailored for teenagers and young adults. During this Delta live-aboard course, students will embark on a transformative 21-day voyage 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$7,695
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Offshore Passage, Bermuda to NYC A Learn-To-Sail Voyage

American Sailing
Availability : Jun 28, 2024
108 / 117 / 208 / 217

Embrace the adventure of a lifetime with our exclusive Learn to Sail vacation. Journey from Bermuda’s serene shores to the iconic Manhattan Marina, mastering the art of sailing and earning ASA credentials on the majestic Arabella. Don’t miss this unparalleled blend of education, adventure, and luxury at sea.

From$3,995$3,799
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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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BVI, The Caribbean A Learn-To-Sail Vacation

South Coast Sailing Adventures
Availability : Dec 2024
103 / 104 / 114 / 111 / 116

Set sail with South Coast Sailing Adventures this December in the BVI’s sailing paradise. Earn ASA Credentials, master sailing with certified instructors, and explore the beauty of the Caribbean. Embark on a unique Learn To Sail Vacation amidst the famous ‘Christmas Winds’ for an unforgettable experience. Discover, learn, and relax in the stunning British Virgin Islands. Join us for an adventure where education meets paradise.

From$2,395
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The Bahamas, Caribbean A Guided Flotilla

Whitecaps Sailing School
Availability : Dec 7-14, 2024

Join Whitecaps Sailing School in the Bahamas for an extraordinary sailing adventure. Explore turquoise waters, encounter dolphins, reefs, and sea turtles, all guided by expert ASA instructors.

From$2,300
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A BVI ESCAPE ABOARD ARABELLA A LUXURY CRUISE

American Sailing
Availability : Dec 2024 | Jan 2025 | Feb 2025

Embark on a transformative journey through the British Virgin Islands aboard Arabella with American Sailing. From the lively shores of Jost Van Dyke to the serene beauty of Virgin Gorda, every moment is promised to be infused with laughter, camaraderie, and pure joy. Lose yourself in the rhythm of island life, where each day brings new adventures and lifelong friendships. Your dream itinerary awaits – let Arabella be your guide through paradise.

From$2,550
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PRICE INCREASES 7/1/24

British Virgin Islands, Caribbean A Guided Flotilla

Annapolis Sailing School
Availability : Jan 31-Feb 7 & Feb 8-Feb 15

Join our vibrant flotilla for an unforgettable voyage through the BVI’s azure waters. Enjoy daily sailing excursions, island hopping, and leisurely activities like snorkeling and beachcombing. Whether you’re a seasoned sailor or a novice, this trip promises endless fun and relaxation in paradise.

From$2,350
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PRICE INCREASES 7/1/24

British Virgin Islands, Caribbean A Learn-To-Sail Vacation

Annapolis Sailing School
Availability : Jan 31-Feb 7 & Feb 8-Feb 15, 2025
104 / 114

Embark on a sailing adventure through the picturesque BVI while earning your ASA 104 and 144 credentials. Our seasoned skippers will guide you through every aspect of sailing, from provisioning to navigation, ensuring a comprehensive learning experience amidst stunning island backdrops.

From$2,350
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