Regattas & Events

January 31 to February 5, 2027

Grenada Sailing Week

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.”

February 3 to February 7, 2027

Caribbean Multihull Challenge Race and Rally 

First held in Sint Maarten in 2019, the annual Caribbean Multihull Challenge has quickly become a cornerstone event dedicated exclusively to multihulls. Participation has grown steadily each year, drawing multihull owners, captains, and crews together to connect, compete, and celebrate their shared passion in the vibrant setting of St. Martin / St. Maarten. In 2023, organizers expanded the event by introducing a cruising rally—designed for skippers who prefer a more relaxed pace but still want to be part of the festivities. You can enjoy the rally on a Moorings catamaran. With both racing and rallying options, the Caribbean Multihull Challenge Race and Rally truly offers something for everyone.

March 4 to March 7, 2027

St. Maarten Heineken Regatta

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.

March 29 to April 4, 2027

BVI Spring Regatta and Sailing Festival

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!

21 to 25 April, 2027

Antigua Sailing Week

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.

May 8 to May 14, 2027

Tahiti Pearl Regatta

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.

July to July, 2026 (Dates pending)

The Seychelles Challenge

The Seychelles Challenge is a 7-day, 6-night active vacation experience featuring daily sailing challenges around the iconic Seychelles Islands. Sailors, sailing enthusiasts, and tourists race in the comfort of The Moorings Chartered catamarans with the option to charter bareboat or with a local skipper. This specially curated island experience is coupled with official functions and daily prize-giving ceremonies hosted at exotic locations on the Seychelles Islands which present visitors with secluded coves, pristine beaches, and vibrant coral reefs teeming with marine life.

October 20 to October 29, 2026

The Moorings Interline Regatta

The Moorings is happy to announce another year of the Interline Regatta held in the British Virgin Islands.

April 18 to April 25, 2027

Boat U.S. BVI Flotilla

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. 

October 15 to October 18, 2026

Annapolis United States Sailboat Show

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.

October 28 to November 1, 2026 

Ft. Lauderdale International Boat Show

Fort Lauderdale, Florida, the “Yachting Capital of the World” will host the Fort Lauderdale International Boat Show in October of 2025. 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.

February 10 to February 14, 2027

Discover Boating Miami International Boat Show

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.