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Caribbean

St. Vincent and the Grenadines ~ Luxury Sail and Stay

Availability : Oct 2023

One of the world’s best kept secrets, discover the enchanting islands of St Vincent and The Grenadines, known as the ‘Gem of the Antilles’. Unwind in one of the most picture-perfect destinations boasting over 30 stunning paradise islands and cays.

From$9,940
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US Virgin Islands A Learn-To-Sail Vacation

Go Sail Virgin Islands
Availability : November - July
101 / 103 / 104 / 106 / 114 / 118

Experience the ultimate sailing charters for groups with tailor-made vacations that cater to your desires. Our local Sailing Virgin Island Captain ensures you get the most out of your journey, offering sailing school, thrilling adventures, snorkeling, island exploration, beach escapades, and delightful local restaurant experiences.

From$3,895
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Caribbean Flotilla ~ British Virgin Islands

Availability : December 2023

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$2,195
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Caribbean Flotilla ~ British Virgin Islands

Availability : December 2023

Sailing in Paradise is a dream of most sailors, yet most never get around to it. Spinnaker not only makes it possible but makes it easy. We have been making the dream come true in B.V.I. for almost 30 years. We make it safe, easy, affordable and memorable.

From$4,600
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Grenada, Caribbean A Learn-To-Sail Vacation

LTD Sailing
Availability : July, August and September 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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Central America Flotilla ~ Islands of Belize

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$2,695
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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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Abaco Island, Bahamas A Learn-To-Sail Vacation

Vagabonde Sailing Adventures
Availability : November to June in the Caribbean and July to September in the Mediterranean
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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Lenny Shabes Sailing Festival ~ BVIs

Availability : June 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$4,500
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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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