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Lenny Shabes Sailing Festival ~ Affiliates ~ British Virgin Islands

hosted by American Sailing
  • 8 Days & 7 Nights
  • June 16 - 22, 2024

The Lenny Shabes Sailing Festival is 6 days and 6 nights of sailing in the British Virgin Islands. This flotilla in paradise is a celebration of the sailing lifestyle and pays tribute to all that Lenny Shabes, our late founder, has done for the world of sailing.

In this flotilla, we anticipate 10-20 boats made up of incredible individuals and schools from around the world, coming together for one amazing week.


We have secured a fleet of boats for our Affiliate schools to charter so everyone can take part. Affiliates can charter boats by booking through American Sailing and then sell cabins to their students. Affiliates can choose to offer cabins on a captained charter or offer a learn-to-sail vacation experience where sailors can earn certifications.

Each boat that is chartered by an Affiliate must have an ASA instructor or qualified captain onboard. We have both monohull and catamaran options available. Boats are first come first serve.

For example, an Affiliate charters a Leopard 404 for $7,701.40 and offers a learn-to-sail vacation for students to earn their 104 & 114 certifications for $4,750 USD per cabin. With one cabin reserved for the instructor the 3 remaining cabins would generate $14,250 USD of revenue.

If you have any questions about this opportunity please contact Roman Manning via email at rmanning@asa.com.

Day 1
June 16th
  • Arrive at Marina
  • Get settled on boat
  • Welcome party
Day 2
June 17th
  • Sail to Norman
  • Snorkeling at the Indians
  • Willy T Glow Party
Day 3
June 18th
  • Sail to Spanish Town
  • Explore the Baths
  • Experience a Coco Maya Dinner
Day 4
June 19th
  • Sail to the North Sound
  • Beach Day at the Bitter End Yacht Club
  • Hobie Cat Regatta
  • Sundowners at Saba Rock
Day 5
June 20th
  • Anegada Regatta
  • Beach day at Anegada 
  • Beach Bonfire
Day 6
June 21st
  • Sail to Jost Van Dyke 
  • Beach day at Soggy Dollar 
  • Foxy’s for sundowners
Day 7
June 22nd
  • Sail from JVD to Marina
  • Boat checkout
Day 8

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



  • Fuel
  • Week of Flotilla Events
  • ASA Marketing Support


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


Leopard 404 Catamaran

  • Cabins: 4
  • Heads: 4
  • Max Sailors: 8
  • A/C: Yes


(includes flotilla fee)

Beneteau 46 Monohull

  • Cabins: 3
  • Heads: 3
  • Convertible Double Berth Saloon: Yes
  • Max Sailors: 8
  • A/C: Yes

(includes flotilla fee)

An initial Deposit of 40% secures the boat.

Payment Due Dates
All charters must be paid in full by March 1st, 2024.

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