Regattas & Events

Whether you're looking to take part in the event as a participant or spectator, The Moorings has something to offer everyone that attends. Call a Moorings Vacation Planning Specialist at 888-952-8420 to receive your quote.

Regattas | Events | Boat Shows


The Moorings Interline Regatta | October 10 - 19, 2023

The Moorings is proud to announce that the Interline regatta will be returning to the British Virgin Islands October 2022.

Grenada Sailing Week | January 29 - February 3, 2023


First established in 2013, Grenada Sailing Week attracts sailing enthusiasts from all over the world. This annual sailing festival takes place off the island’s southern coast, based out of the new Port Louis Marina. There will be a great mix of popular and new courses to provide challenging sailing for top-quality international keelboats from the UK, USA, Europe, and with strong competition from local yachts from Grenada & the Caribbean Region. Once the racing is over, skippers and crews will be treated to a great party program. Join us and experience great sailing and fun on "The Spice Isle of the Caribbean."

St. Maarten / St. Martin Caribbean Multihull Challenge Race and Rally | February 3 - 5, 2023


The Caribbean Multihull Challenge is the Northern Hemisphere’s largest multihull-only regatta. Organized by the Club that created the world-famous St. Maarten Heineken Regatta — this three-day celebration of the technology and lifestyle that makes multihulls yachts so special is growing annually. Racing in a multihull-only regatta is different with thrilling downwind or reaching starts, and courses with long off-the-wind legs to take advantage of multihull speed. For 2023 the Club is introducing a Multihull Rally during the same time period that will offer cruising sailors great sailing and shore-side fun - no racing - in French Anse Marcel and in Anguilla. Celebrate your difference. Registration is now open at

St. Maarten Heineken Regatta | March 2 - 5, 2023


This world-renowned sailing event offers four days of World Class Racing, with trade winds coming from the North East, an average temperature of 25°C, and crystal clear waters. This truly international event had a staggering 37 different countries represented during the 2016 Regatta. Courses will take participants along coastal races, as well as around the island, presenting the beautiful beaches, rock formations, and other scenery. On shore participants and visitors will be able to enjoy the culture, cuisine, and music from both the Dutch and French sides.

BVI Spring Regatta and Sailing Festival |  March 27 - April 3, 2023


One of the Top Sailing Regattas in the Caribbean. 7 days of perfect wind, warm water, and hot racing! Join over 150 yachts from around the world to race on three-course areas, 18 classes, something for everyone.

And the Parties - you’ve gotta be there!

Antigua Sailing Week | April 29 - May 5, 2023


The “granddaddy of Caribbean regattas,” Antigua Sailing week has become one of the world’s premier yacht racing events since its humble beginnings more than 50 years ago. Today, the event features more than 100 yachts ranging in size from 24 to 100+ feet, all of which come together for an exciting race along the southern coast of Antigua. Join the races yourself, charter a spectator yacht for an up-close view of the action, or watch the competition from vantage points along the shore. Either way, you’ll get to experience one of Antigua’s most exciting annual events.

Tahiti Pearl Regatta | May 17 - 20, 2023 


If you’re in need of an excuse for a Tahiti sailing escape, you’ve found it! Specialist or yachtsman, experienced or beginner, or just looking for festive evenings in an enchanting setting, welcome to the Tahiti Pearl Regatta. It combines sailing and dugout canoe Regattas and allows you to meet like-minded sailors as well as explore an amazing island paradise.


SailEATalia Sail, Wine, and Taste of Italy Flotillas


Sailitalia is now hosting two SailEATtalia Sail, Wine, and Taste of Italy flotillas in Procida and Sicily. Each exclusive flotilla departs from its prospective Moorings charter base and follows a specialized itinerary. This one-of-a-kind group charter experience takes your palate on an unforgettable journey in a premier destination known for its flavorful cuisine, indulgent desserts, and award-winning wines. SailEATalia guests will even enjoy one day in the company of a professional chef, tasting dishes and learning how to prepare them at home.

Offshore Sailing Flotilla Cruises | 2022 & 2023


Offshore Sailing School's very first flotilla cruise took place in August 1973 in the British Virgin Islands! Founders Steve and Doris Colgate led that cruise and hundreds more. They have now turned the helm over to the Atwaters, an accomplished sailing team that will take you places you might never go on your own. In 2022 join an Offshore Sailing School flotilla sailing vacation on board our The Moorings fleet in Seychelles, the BVI, The Abacos Bahamas, or Thailand.

View More Details and Itineraries

BoatU.S. BVI Flotilla | May 20 - 27, 2023


When BoatU.S. members come together for a group charter adventure, good times and unforgettable vacations follow right behind. The Moorings is excited to invite flotilla veterans and first-timers alike to the British Virgin Islands for this annual BoatU.S. members-only excursion. Book your yacht today to secure a spot while they are still available. 

Boat Shows

St. Petersburg Power and Sailboat Show | January 19 - 22, 2023


Come join us at the largest boat show on the Gulf Coast! The 44th annual St. Petersburg Power & Sailboat Show will feature an exciting selection of powerboats and sailboats.

 Annapolis United States Sailboat Show | October 13 - 17, 2022 


In October sailors from around the globe gather on miles of docks in beautiful downtown historic Annapolis for the United States Sailboat Show. This is an internationally acclaimed sailboat show, recognized as the largest, most prestigious, and oldest in-water sailboat show in the world.

 Ft. Lauderdale International Boat Show | October 26 - October 30, 2022


Fort Lauderdale, Florida, the "Yachting Capital of the World" will host the Fort Lauderdale International Boat Show in October of 2022. Show exhibits range from yacht builders and designers to exotic cars and brokerage yachts. A wide variety of boats will be on display including runabouts, sport fishers, high-performance boats, center consoles, cabin cruisers, flats boats, skiffs, express cruisers, sailing yachts, motor yachts, bowriders, catamarans, ski boats, jet boats, trawlers, inflatables, canoes, and extraordinary superyachts.

Discover Boating Miami International Boat Show | February 15 - 19, 2023


Hailed as “The Ultimate Boat Show. An Epic Event.” Miami’s International Boat Show at the Miami Marine Stadium Park & Basin welcomes more than 100,000 visitors from around the globe. Around a thousand boats and hundreds of exhibitors make this show one of a kind.