Regattas & Cruising Rallies in Caribbean & Central America

Caribbean Multihull Challenge

Location: St. Maarten / St. Martin, Caribbean & Central America Categories: Regattas & Cruising Rallies

Regatta dedicated exclusively to multihull yachts.

Grenada Sailing Week

Location: Grenada, Caribbean & Central America Categories: Regattas & Cruising Rallies

The popular Grenada Sailing Week regatta is scheduled to run again in 2024.

Jolly Harbour Annual Yacht Club Regatta

Location: Antigua, Antigua and Barbuda, Caribbean & Central America Categories: Regattas & Cruising Rallies

Jolly Harbour Valentines Regatta

Location: Antigua, Antigua and Barbuda, Caribbean & Central America Categories: Regattas & Cruising Rallies

Jolly Harbour Yacht Club invites yachts/ sailors to participate in a weekend of racing and social activities during the weekend of 10th to 12th February 2023.

Jolyon Byerly Hightide Racing Series

Location: Antigua, Antigua and Barbuda, Caribbean & Central America Categories: Regattas & Cruising Rallies

Hosted by the Antigua Yacht Club, this is a Christmas two-day race series open to all keel boats.

Nelsons Pursuit Race

Location: Antigua, Antigua and Barbuda, Caribbean & Central America Categories: Regattas & Cruising Rallies

Open to all yachts, with a staggered start, this fun New Year's Eve pursuit race is in honour of Lord Nelson’s pursuit of Admiral Villeneuve around the Caribbean!

Oyster World Rally 2024-25

Location: Antigua, Antigua and Barbuda, Caribbean & Central America Categories: Regattas & Cruising Rallies

Starting from and finishing in Antigua - 27,000 miles over 6 months!

Peters & May Round Antigua Race

Location: Antigua, Barbuda, Antigua and Barbuda Categories: Regattas & Cruising Rallies

The Peters & May Round Antigua Race has been exciting and popular with many Antigua Sailing Week participants for many years.

RORC Nelson's Cup Series & Antigua 360

Location: Antigua, Antigua and Barbuda, Caribbean & Central America Categories: Regattas & Cruising Rallies

13-16 February, 2024

RORC Transatlantic Race

Location: Lanzarote, United Kingdom, Spain, Grenada, Canary Islands, Caribbean & Central America Categories: Regattas & Cruising Rallies

An annual 3000 mile Trans-Atlantic Race from Marina Lanzarote to Port Louis, Grenada.

Regattas & Cruising Rallies

Location: British Virgin Islands Categories: Shoreside Activities & Events, Regattas & Cruising Rallies

USA to the Caribbean in November 2021.

Round The Rocks Race

Location: U.S. Virgin Islands, Caribbean & Central America Categories: Regattas & Cruising Rallies

Drag race from St. Thomas to St. John – a prelude to the STIR regatta.

St Barth’s Yacht Club

Location: St. Barth’s Categories: Yacht Clubs, Regattas & Cruising Rallies

Sailing school, private lessons, rental of 7.5m keelboats, kayaks & paddle boards.

St Barth’s Yacht Club - New Year’s Eve Regatta

Location: St. Barth’s, Caribbean & Central America Categories: Regattas & Cruising Rallies

A friendly 24 mile 'Around the Island' pursuit race that takes place on December 31.

St Thomas International Regatta - STIR

Location: U.S. Virgin Islands, Caribbean & Central America Categories: Regattas & Cruising Rallies

The STIR always attracts a healthy and competitive fleet of well sponsored and well-prepared professional racing yachts.