June 16, 2024

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Lenny Shabes Sailing Festival ~ British Virgin Islands

hosted by American Sailing
  • 6 Days & 6 Nights
  • June 16 - 22, 2024

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 watch the sunset at Foxy’s. It’s going to be an action packed sailing adventure!


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. 


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.


The light and airy Sunsail 404 combines the virtues of the much loved Sunsail 444 and 384. Neither too big nor too small, this versatile catamaran has all the mod-cons to put it at the very forefront of the fleet. An open-plan saloon and sliding doors allow easy access via the saloon to bow and stern. The four private, spacious and cool double cabins share two larger heads and shower spaces between them. The cabins offer plenty of storage space and adequate head room for comfortable living. On deck, the helm position provides good visibility and control. Electric winches make for easy sail trimming, while a relatively large sail area combines with a forgiving low aspect rig to balance power and stability.

Learn To Sail

For those looking to learn to sail on vacation, we will pair you with other students earning certifications so that you’re onboard the same boat with one of our American Sailing Certified instructors. After a day of learning you’ll be able to relax and joining the rest of the flotilla for all the fun activities we have planned. Book your Learn To Sail Vacation. 

Learn To Sail Vacation Booking Form

If you would like to learn to sail during the Lenny Shabes Sailing Festival then please fill out the form below and we’ll match you up with right boat and instructor. If you just want to enjoy all that the BVI has to offer with a captained charter please select a cabin.

    First Name*
    Last Name*
    Email Address*
    Telephone Number*
    Current Certifications
    Certifications You Are Interested In

    June 16th
    • Arrive at Marina in the early afternoon
    • Get settled on the boat
    • Welcome party
    June 17th
    • Sail to Norman
    • Snorkeling at the Indians
    • Willy T Glow Party
    June 18th
    • Sail to Spanish Town
    • Explore the Baths
    • Experience a Coco Maya Dinner
    June 19th
    • Sail to the North Sound
    • Beach Day at the Bitter End Yacht Club
    • Hobie Cat Regatta
    • Sundowners at Saba Rock
    June 20th
    • Anegada Regatta
    • Beach day at Anegada 
    • Beach Bonfire
    June 21st
    • Sail to Jost Van Dyke 
    • Beach day at Soggy Dollar 
    • Foxy’s for sundowners
    June 22nd
    • Sail from JVD to Marina
    • Boat checkout by late morning
    • Departure

    *Itineraries are subject to change due to weather or other circumstances beyond our control.

    The Details


    • Luxury cabin onboard a Lagoon 424 catamaran, including private head/shower.
    • Provisions for 6 days – Breakfast, Lunch, Snacks, Water
    • Fuel
    • Skipper / Instructor


    • Dinners
    • Alcoholic Drinks
    • Snorkel Equipment / Water Sports
    • Shoreside Activities
    • Skipper Gratuity
    • BVI Tourist Tax
    • Travel 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.


    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.


    Prices start at $4,500 USD per cabin. Limit 2 sailors per cabin


    An initial Deposit of 40% secures your cabin.

    Payment Due Dates

    All registrations must be paid in full by March 1st, 2024.

    Refunds / Cancellations

    Payments/Deposits will be refunded in full if a reservation is canceled before December 1st, 2023. Cancellations after December 1st, 2023 are non-refundable.