Caribbean

Lenny Shabes Sailing Festival ~ Affiliates ~ BVIs

Availability : June 2025

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.

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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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Barbados A Learn-To-Sail Vacation

Wet & Salty Adventure Sailing School
Availability : Jan 19 / Mar 01, 2025
101 / 103 / 104

Embark on the ultimate sailing adventure with our comprehensive 9-day ASA Liveaboard Monohull Class. This immersive course is designed for aspiring sailors seeking to master the essentials of sailing, with hands-on training and real-world experience. Over the span of a week, you will cover ASA 101, 103, and 104 certifications, ensuring you are well-prepared to handle various sailing conditions and navigate with confidence!

From$3,350
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U.S. Virgin Islands A Learn-To-Sail Vacation

Go Sail Virgin Islands
Availability : February 9-15 & March 2 - 8
103 / 104 / 114 / IPC

Set sail in the US Virgin Islands with Go Sail Virgin Islands Sailing School. Learn essential sailing skills on a Leopard 44 Catamaran, exploring St. Thomas, St. John, and St. Croix. Enjoy expert instruction, small class sizes, and earn internationally recognized certifications for an unforgettable Caribbean adventure.

From$3,150
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British Virgin Islands, Caribbean A Learn-To-Sail Vacation

Sea Safaris Sailing School
Availability : Feb 16-22 & Feb 24-Mar 01, 2025
103 / 104 / 114 / 116

The BVI provides the perfect mix of hands-on learning, scenic beauty, and plenty of leisure activities, making it an unforgettable destination for both sailors and those looking to enjoy a tropical escape.

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British Virgin Islands, Caribbean A Guided Flotilla

SailNashville
Availability : Feb 22 - Mar 01

The BVIs are the perfect destination for your first charter experience. A flotilla gives you the support group that makes that first charter experience even easier. And the weather in late February in the BVIs is some of the best.

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CHRONOS IN THE CARIBBEANA LUXURY CRUISE

American Sailing
Availability : March 2025

Sailing in the Grenadines allows you to experience a variety of landscapes and activities. You can anchor in a quiet cove for a day of swimming and snorkeling, visit lively markets and historic sites onshore, or enjoy a sunset from the deck of Chronos. The Tobago Cays, a protected marine park, is a highlight, offering some of the best snorkeling and diving in the Caribbean.

From$4,050
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2025

Lenny Shabes Sailing Festival ~ BVIs A Guided Flotilla

American Sailing
Availability : June 15-21, 2025

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$2,499
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