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Jun 15-21, 2025
British Virgin Islands
4,998 / cabin

Lenny Shabes Sailing Festival

The 2nd Annual Lenny Shabes Sailing Festival
Luxury Catamarans
Explore the BVI's
Fun Shoreside Events
Skippered Charter
One Massive Flotilla

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.

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ONLY 3 SPOTS LEFT

“Lenny often spoke of creating an event where we celebrated the sailing lifestyle as one large group of like-minded sailors. This event will add to Lenny’s legacy and his vision for American Sailing.”
~ Cindy Shabes, President of American Sailing
Learn more about Lenny Shabes

Lenny Shabes Sailing Festival

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FESTIVAL OVERVIEW

Enjoy 6 days and 6 nights of sailing alongside fellow boats for one epic flotilla experience. Explore the iconic baths, kick back and relax at the famous Bitter End Yacht Club, and have a sundowner at Foxy’s. We will have an action packed 6 days awaiting you when you step aboard.

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THE FLOTILLA

A flotilla is a group of boats sailing together from destination to destination, sharing the joy of being on the water and the excitement of what’s ashore. In this flotilla, we anticipate 10-20 boats made up of incredible individuals from around the world, coming together for one amazing week. Book your cabin with American Sailing and you’ll have your own skipper, a luxury catamaran, and a dream sailing vacation waiting for you.
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The British Virgin Islands

The British Virgin Islands are an idyllic Caribbean destination known for their pristine beaches, crystal-clear waters, and stunning natural scenery. With over 60 islands and cays to explore, there are plenty of options for visitors looking to soak up the sun, relax on the beach, and enjoy the island's laid-back atmosphere. The British Virgin Islands' consistent trade winds and calm seas provide perfect sailing conditions for both beginners and seasoned sailors. Island-hopping is a breeze, allowing travelers to immerse themselves in various cultures, cuisines, and activities. Water sports abound, from snorkeling and diving to paddleboarding, ensuring there's always something exciting to do. Whether you seek adventure, relaxation, or you aim to expand on your sailing education, sailing through the British Virgin Islands offers an irresistible destination for anyone looking to experience the Caribbean's finest treasures.

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The Boat

You’ll be cruising aboard a luxury sailing catamaran, 42ft or larger. All the yachts have spacious, queen-sized cabins with their own head/shower, air conditioning throughout, and a generator. While you’ll be spending most of your time outside, the interiors are both spacious and stylish. The yachts have fully equipped galleys and comfortable saloon areas. Cockpit areas are well-ventilated and sheltered, the perfect spot to socialize with new friends! You’ll find various seating areas around the yacht, in the cockpit, on the bow, on the coach roof, and on the flybridge, all perfect for sunbathing, lounging, and enjoying a drink or three! Sail controls are located by the helm station, making these yachts great to get everyone involved in the activity.
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The Schedule

SUNDAY | JUN 15

Arrive at the marina in the afternoon

Get Settled on boat

Welcome Party

Monday | JUN 16

Sail to Norman

Snorkeling at the Indians

Willy T Glow Party

Tuesday | JUN 17

Sail to Spanish Town
Explore the Baths

Experience a Coco Maya Dinner

Wednesday | JUN 18

Sail to the North Sound

Beach Day at the Bitter End Yacht Club
Hobie Cat Regatta

Sundowners at Saba Rock

Thursday | JUN 19

Anegada Regatta

Beach day at Anegada

Beach Bonfire

Friday | JUN 20

Sail to Jost Van Dyke
Beach day at Soggy Dollar
Foxy’s for sundowners

Saturday | JUN 21

Sail from JVD to Marina

Boat checkout completed by late morning

Departure

The Details

What's Included

  • Luxury cabin onboard a 42' catamaran, including private head/shower.

  • Provisions for 6 days - Breakfast, Lunch, Snacks, Water

  • Fuel

  • Skipper / Instructor

What's Not Included

  • Dinners

  • Alcoholic Drinks

  • Snorkel Equipment / Water Sports

  • Shoreside Activities

  • BVI Tourist Tax

  • Skipper Gratuity

  • Travel Insurance

Insurance

Travel insurance is important for travelers who need a solution to protect themselves from unexpected situations that could affect their travel plans, trip investment and health when traveling. It's practically indispensable on international trips, and for travelers of all ages and occupations, it's a great safety net to give peace of mind when traveling. TravelInsurance.com can help you find an appropriate domestic or international travel insurance policy that meets your needs. You can compare all of your trip insurance options, procure coverage online and travel worry-free.

Travel

The flotilla will depart from the marina in Road Town, Tortola. Common options for getting there include flying into Tortola, BVI (EIS) or into St. Thomas, USVI (STT) and taking the ferry from St Thomas - Road Town.

Pricing

Prices start at $4,998 USD and up per cabin. Limited to 2 sailors per cabin.

Deposits
Initial Deposit of 40% secures your registration.

Payment Due Dates
All registrations must be paid in full by March 14th, 2025.

Refunds / Cancellations
Payments/Deposits will be refunded in full if a reservation is canceled before March 14th, 2025. Cancellations after March 14th, 2025 are non-refundable.