Jun 16-22, 2024
British Virgin Islands
4,500 / cabin

Lenny Shabes Sailing Festival

Introducing the 1st 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.


“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



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.



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

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 Boat

The Lagoon 424 is an award winning sailing catamaran that has four luxury cabins each featuring their own head/shower. The thoughtfully-designed interior is both spacious and stylish, delivering onboard comfort when anchored or underway. It has a spacious cockpit that is well-ventilated and sheltered, in addition ample space all around the boat for outdoor activities and sunbathing. The helm station is located on the flybridge, offering an unobstructed view of the surroundings and easy access to the sail controls. The catamaran is known for its balance, high performance, and smooth handling under sail. The generator, air-conditioning, and watermaker, ensure an enjoyable luxury charter experience.



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 floitlla for all the fun activities we have planned.

The Schedule


Arrive at the marina in the afternoon

Get Settled on boat

Welcome Party

Monday | JUN 17

Sail to Norman

Snorkeling at the Indians

Willy T Glow Party

Tuesday | JUN 18

Sail to Spanish Town
Explore the Baths

Experience a Coco Maya Dinner

Wednesday | JUN 19

Sail to the North Sound

Beach Day at the Bitter End Yacht Club
Hobie Cat Regatta

Sundowners at Saba Rock

Thursday | JUN 20

Anegada Regatta

Beach day at Anegada

Beach Bonfire

Friday | JUN 21

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

Saturday | JUN 22

Sail from JVD to Marina

Boat checkout completed by late morning


The Details

What's Included

  • Luxury cabin onboard a Lagoon 424 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


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. 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 and up per cabin. Limited to 2 sailors per cabin.

Initial Deposit of 40% secures your registration.

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, 2024 are non-refundable.