Home   >   Articles   >   Love Sailing? Check Out these Five Annual Regattas and Boating Events in the Caribbean

Love Sailing? Check Out these Five Annual Regattas and Boating Events in the Caribbean

by Karen Rollins Sep 11, 2023

Share this

Sailing in the Caribbean is a regular pastime for many people who like to take full advantage of the beautiful oceans and seas surrounding our islands.

Over 100 sailing events are held in the Caribbean every year, so whether you are a seasoned or novice sailor or just a boating enthusiast there are plenty of activities to keep you entertained.

We’ve listed just a few below to whet your appetite (get it!)

Round Barbados Sailing Week

The Round Barbados Sailing Week is held every year in January and is the opening event on the Caribbean Sailing Association’s regatta circuit.

The action begins with a weekend of dinghy races and the surf and kiteboarding competitions, followed by offshore sailing races, and then the Mount Gay Round Barbados Race on the last Sunday.

Most of the sailing, prize giving, and after-parties with live music take place in Carlisle Bay and at the Barbados Yacht Club and Barbados Cruising Club. 

Grenada Sailing Week

Grenada Sailing Week (GSW) is one of the first regattas on the Caribbean Sailing Association’s annual calendar held at the end of January just before the Grenada Sailing Festival.

GSW typically attracts around 40 participating boats with approximately 350 sailors from 20 countries. The racing takes place between two venues – Camper & Nicholson’s Port Louis Marina and Secret Harbour Marina.

As well as excitement on the waves, the week also features plenty of land-based activities, including nightly parties.

Turks and Caicos – Valentine’s Day Cup

All the family will be enraptured by this annual event which features a regatta of model Caicos Sloop sailboats racing in the calm waters at beautiful Bambara Beach on the Saturday nearest Valentine’s Day. 

Model sailboat building is a large part of Turks and Caicos culture, especially for older generations. In the Valentine’s Day Cup (which has been running since 2000), competitors traditionally build their miniature sailboats by hand with bark from the gum-elemi tree. There are three classes of races with cash prizes for the winners. 

Local food and drink, as well as live music, add to the party atmosphere.

Antigua Classic Yacht Regatta

Three days of exhilarating yacht racing awaits participants and fans who make it to Antigua for the annual Classic Yacht race which takes place in April just before Antigua Sailing Week.

The event features three main races; Old Road race on Friday, Butterfly race on Saturday, and the modified Kenny Coombs Memorial Cannon on Sunday.

Some other activities attendees and spectators can look forward to are the Single-Handed Race and the Concours d’Elegance, the Parade of Sail into English Harbour, and Gig Racing and Cream Teas. All the main action takes place at Nelson’s Dockyard.

Bonaire Sailing Regatta

Bonaire celebrates its strong sailing tradition every October with its International Sailing Regatta. 

Sailors of all classes visit Bonaire to race between the main island and Klein Bonaire or on the north side of Klein Bonaire. 

Participants and spectators are also treated to dancing, music, food, and drink. The entire island takes on a festive atmosphere during this time of year and visitors from all over the world are encouraged to take part.

St Lucia’s Mango Bowl

Billed as the “premiere annual keelboat regatta” on the island, The Mango Bowl Regatta was first held in St Lucia in 2012. 

Hosted by the St Lucia Yacht Club (SLYC), this regatta in November features two days of exciting races involving four classes – J24, Surprise, Racing and Cruising. 

The event ends with a prize-giving ceremony and BBQ at the yacht club on a Sunday afternoon.

St Lucia – Atlantic Rally for Cruisers

Described as “the world’s largest and most successful trans-ocean sailing event,” the Atlantic Rally for Cruiser (ARC) has been running since 1986.

Participants sail 2,700 nautical miles across the Atlantic Ocean on a direct route from Las Palmas de Gran Canaria to Rodney Bay Marina in St Lucia. They leave in late November and the journey usually takes around eight to 31 days to complete depending on the vessel and trade winds.

Entrants enjoy a warm Caribbean welcome when they make it to St Lucia just before Christmas. St Lucia has been the rally’s home base for over 30 years.

You may also like: Love live music? Check out these five music festivals in the Caribbean