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


Grenada Sailing Week | January 2021 TBC


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. Martin Caribbean Multihull Challenge | February 4 - 7, 2021


The Caribbean Multihull Challenge is the Northern Hemisphere’s largest multihull-only regatta. Organized by the Club that creates the world-famous St. Maarten Heineken Regatta - this three-day celebration of the technology and lifestyle that makes multihull yachts so special is growing annually. Racing in a multihull-only regatta is different with thrilling downwind or reaching starts; and courses designed with long legs to take advantage of multihull speed. For 2021, racing around the windy and cruiser-friendly Leeward Island takes place in waters on both the French and Dutch sides with prize giving’s and after-parties held at social hot spots. Celebrate the difference. Be there!

St. Maarten Heineken Regatta | March 4 - 7, 2021


The St. Maarten Heineken Regatta will celebrate its 41th edition from March 4 - March 7, 2021. 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 side.

BVI Spring Regatta and Sailing Festival | March 29 - April 4, 2021


One of the Top Sailing Regatta's 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 24 - 30, 2021


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 11 - 15, 2021 


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.

38th Annual Interline Regatta | October 12 - 21, 2021

The Moorings is proud to present the 38th Annual Interline Regatta in the British Virgin Islands in October of 2021. Open to members of the airline industry, their families and friends, the Interline Regatta features a variety of events for both sailors and spectators alike. In addition to numerous boat races throughout the islands, the regatta hosts a variety of nightly theme parties, making it perfect for anyone looking for non-stop celebration in a beautiful island setting.


The Moorings Croatia Rendezvous | October 10 - 17, 2020


This fall, join The Moorings for a special on the water rendezvous event to experience the ever-enchanting Dalmatian Coast in Croatia. Reserve your yacht today and join other like-minded charterers for a week of island-hopping filled with exclusive dinners and events. Don't miss this opportunity to discover the best of Croatia under the expert guidance of your lead boat crew.

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.

Fireball Full Moon Parties


Don’t miss the British Virgin Island’s best monthly tradition. Full Moon Parties are the place to be for a true taste of BVI culture and nightlife. Held on the night of the full moon each month, these beachside celebrations feature food, artists, live music, dancing, fire jugglers and more! There are two places to celebrate on Tortola: Bomba’s Shack on the eastern coast and Trellis Bay on Beef Island. Trellis Bay is better suited for families while Bomba’s offers a more party-like atmosphere.

 2020 Dates

  • Friday, January 10
  • Sunday, February 9
  • Monday, March 9
  • Wednesday, April 8
  • Thursday, May 7
  • Friday, June 5
  • Sunday, July 5
  • Monday, August 3
  • Wednesday, September 2
  • Thursday, October 1
  • Saturday, October 31
  • Monday, November 30
  • Wednesday, December 30

 2021 Dates

  • Thursday, January 28
  • Saturday, February 27
  • Sunday, March 28
  • Monday, April 26
  • Wednesday, May 26
  • Thursday, June 24
  • Friday, July 23
  • Sunday, August 22
  • Monday, September 20
  • Wednesday, October 20
  • Friday, November 19
  • Sunday, December 19


Offshore Sailing Flotilla Cruises | 2021


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 2021 join an Offshore Sailing School flotilla sailing vacation on board our The Moorings fleet in Belize, Greece, the Seychelles or the BVI.

View More Details and Itineraries

BoatU.S. BVI Flotilla | May 22 - 29, 2021


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 | December 3 - 6, 2020


The 43rd annual St. Petersburg Boat Show is one of the largest boat shows in Florida! Plan your visit and prepare to tour our flagship yachts. Stay another day to enjoy one of the many attractions the city itself and Tampa Bay as a whole have to offer.

Miami International Boat Show | February 11 - 15, 2021


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.

Pacific Sail and Power Boat Show | April 2021 (dates TBC)


Whether as a newbie or a seasoned boating enthusiast, this four day spectacular is the place to immerse oneself in the world of marine sports! Enjoy the stunning waterfront venue while discovering all the new boats that the world’s leading manufacturers have to offer.  Also on display will be a full range of marine electronics, gear, products and accessories.

 Annapolis United States Sailboat Show | October 2021 (dates TBC)


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.