Caribbean Regattas 2024

The Caribbean knows how to party, but best of all it knows how to sail. Here is our run down on where you can join in on the action.
Words: Frances and Michael Howorth

Switch on the VHF and wait for the Caribbean weather forecast during the first few months of every year. It will state “Winds out of the East, 12 to 25 knots, slight seas and long swells under a partially cloudy sky.” How do we know? We lived in the Caribbean onboard yachts for nearly a decade, and we learned the script off by heart.

Perhaps that is why the Caribbean has spawned so many wonderful sailing regattas. That is not to diminish the power of cold tins of Heineken or stubby brown bottles of Red Stripe. Racing is hard at this time of year but equally it is exhilarating in the extreme. And when it is all done, and the silverware has been collected there is the sound of steel drums and dancing to go alongside the barbecued jerk chicken and rum punch.

Here is our run down on where you can join in on the action.

Barbados, 17th to 22nd Jan
Barbados Sailing Week often called the Mount Gay Rum Regatta is set to run from 17th to the 24th of January 2024. It offers a unique mixture of ocean sailing, racing, and an unbeatable Bajan welcome!

The first documented organised sailing boat race around Barbados was held on January 1st, 1936. Then five trading schooners competed for ‘bragging rights’ and a small prize. Whilst most boats sailed for the honour of the fastest time, the consolation prize of a barrel of Mount Gay Rum for the slowest certainly spurred on some captains and had to be discontinued after two boats remained at sea for days stalling to take the prize.

In recent years, the Mount Gay Round Barbados race has been held in January each year to honour the first prime minister of Barbados, The Right Excellent Errol Walton Barrow, known to many as ” Dipper” or “Skipper” and the “father of the nation”. Not only did he lead Barbados to independence from Britain, but he also had an enthusiasm for sailing and was the co-founder of the Barbados Cruising Club. An inclusive sailing and social club open to all Barbadians.

Grenada Sailing WeekGrenada, 28th Jan to 2nd Feb
Spice it up in Grenada during a week-long regatta at the end of January. Grenada Sailing Week runs from the 28th of January through until 2nd February 2024. Grenada, the Isle of Spice, is a beautiful island with rainforests, lakes and waterfalls and mile long beaches. Grand Anse beach is consistently voted one of the best in the Caribbean with excellent hotels, many of which have won international awards, fabulous cuisine both local and international. Superyacht berths are available at Port Louis Marina and racing is split between there and the smaller Secret Harbour marina.

RORC 600 12th to 23rd Feb
Yachts racing under IRC and Multihulls racing under the MOCRA Rule including IRC Two-Handed, Classics, Superyacht, and Class40 will be lining up for the 15th edition of the RORC 600 on 19 February 2024. Starting from Fort Charlotte, Antigua the event now in its 15th year is organised by the Royal Ocean Racing Club in association with the Antigua Yacht Club.

Since the first edition in 2009, the race around 11 Caribbean islands, starting and finishing in Antigua, has evolved into one of the world’s most famous 600-mile races. The 2024 edition has already attracted 40 teams from around the world.

The 2024 RORC Nelson’s Cup Series will start on February 13th. The new fixture was introduced last year and gives teams the opportunity of racing in all or part of a series of six races, including the Antigua 360, round the island race.

Heineken Regatta 28th Feb to 3rd March
Now in its 44th year, the St Maarten Regatta started with a modest 12 sail boats taking part. Thanks to sponsorship and support from Heineken, the event has grown to become one of the largest and perhaps most popular of the Caribbean events, with a record 284 boats participating in 2008.

With the tag line of “Serious Fun!” the 4-day racing schedule is designed to suit everybody from Maxis and Volvo 65s and 70s, one design keel boats through to the Diam 24 trimarans and the more relaxed “Island Class” which attracts cruisers and round the world travellers keen to enjoy taking part in a world class regatta. The world class race officer and event management team make the most of the waters around St Maarten to set variety of courses for each class, and everyone enjoys the challenge of the “Round Island” race, a firm favourite for all taking part.

A key attraction for many is the Bridge Show, with yachts and crews showing off their fancy dress prowess to impress the judges stationed at the St. Maarten Yacht Club right beside the bridge, before heading ashore to the Port de Plaisance Regatta Village to belly up to the sustainably-built bar to chug a cold Heineken, Titos cocktail or glass of Veuve Clicquot champagne and celebrate another fantastic day of racing in paradise. The “Serious Fun!” continues onshore with nightly live performances at the Regatta Village, Greenzone after-parties at the island’s top venues, and a glittering prize giving on stage prior to the final night’s grand finale concert.

St Barth Bucket, 21st to 24th March
In terms of superyacht racing the St Barths Bucket has achieved legendary status. There is no other regatta of its magnitude on the superyacht racing circuit. For over 37 years since 1986, the world’s premier superyacht sailing vessels, owners, crew, and guests have come together for the pleasure and enjoyment of a camaraderie formed between like-minded individuals. The first ever Bucket Regatta was organised in Nantucket, as a birthday celebration for the millionaire yachtsman, Nelson Doubleday. Seven sailing superyachts raced on a hastily prepared 15-mile course on Nantucket Sound that day and the ledgend was created.

In 1995, the French island of St Barths hosted its first Bucket Regatta, and it has done so in March every year since then. Although the size of the yachts and competing fleet has grown significantly, the spirit of the event has remained unchanged.

In recent years, 40 or more superyachts have gathered to compete for the Bucket in glamorous St Barths. Many of the world’s most notable and accomplished sailors have participated in the racing. Nonetheless, as the Bucket Regatta has evolved, the organisers have kept a tight focus on maintaining the original camaraderie and non-commercial spirit of the event.

Saint Thomas International Regatta, 27th to 30th March
The year 2024 sees the 50th outing of the St. Thomas International Regatta (STIR). Set for the Easter Weekend – March 29-31, 2024, this will be the 50th anniversary of what the organisers call the ‘Crown Jewel’ of Caribbean Racing.

For a half-century, STIR has been a beacon that attracts some of the best sailors, everyone from America’s Cup, Olympic, and one-design World Champions to long-time podium-placing teams from the Caribbean and the U.S. with second and third generations as crew.

First held in October 1974, and started by St. Thomas Yacht Club (STYC) organisers to attract top international sailors to race in ideal sailing conditions, STIR continues to be the destination for world-class racing. The chance to trade tacks and tactics with professional crews and talented weekend warriors on professionally set round-the-island and round-the-buoy courses attracts first-timers and keeps long-time competitors coming back.

The Round the Rocks Race (RTR) circumnavigates the neighbouring island of St. John on the day before the start and is a terrific opportunity to tune up for STIR and provides an additional chance to land a podium finish.

BVI Spring RegattaBVI Spring Regatta, 2nd to 7th April
Warm Water and Hot Racing at the most fun sailing regatta in the Caribbean. That’s the boast from the organisers of the BVI Spring Regatta & Sailing Festival where the fun dial is full-on, and the racing and parties are among the best that the Caribbean has to offer.

The seven-day event starts on Monday April 1 (no joke) with the Sailing Festival opening day festivities and skipper pack collection. The Sailing Festival, a warmup event, runs for the first two days with fun, relaxed racing on the agenda. The traditional Round Tortola Race takes sailors on a 37 nautical mile race around the island of Tortola. The next day the Scrub Island Invitational will take sailors some 12 miles upwind to a fabulous island party hosted by Scrub Island Resort. The relatively short race should give sailors plenty of time to enjoy the outstanding Island hospitality.

The Regatta attracts a diverse fleet of boats in addition to a strong bareboat fleet, and whether sailors participate in all five races of the BVI Spring Regatta & Sailing Festival, part or all of the Festival, or the three-day Regatta, there is something for everyone, on the water and shore-side.

Le Voiles de St Barths 16th to the 22nd April
The regatta Les Voiles de St. Barth, was first held in 2010. It was created especially for Saint Barth and continues the long, colourful history of sailboat racing on the island. This started with Loulou’s Regatta back in the 1970’s with its 100 sailboats and continued to embrace the Transat AG2R, the Route du Rose, and the St Barth Bucket Regatta. Since its debut, Les Voiles has continued to grow, to become one of the most important French regattas in the Caribbean. Spread over 5 days, 80 boats manned by 1200 sailors with race in the sun for fun and glory and the chance to win a nice tick-tock.

Watchmakers Richard Mille have become the title partner of the event, which now explains why the regatta will now be known as Les Voiles de St. Barth Richard Mille. Highly competitive sailing and the art of luxury horology seem to go hand in hand. Both embrace extreme performance, the latest technology, and strong artistic dimensions, as well as respect for traditions and the discipline required. These values will be reinforced again as the 2024 edition becomes totally eco-responsible.

Antigua ClassicAntigua, Classic Week 17th to 22nd April
The magical combination of serious racing, laid-back Antigua hospitality, plenty of rum, sunshine, and great camaraderie in a friendly relaxed atmosphere, places the Antigua Classic Yacht Regatta in a class of its own.

Back in the 1960’s at the end of a busy charter seasons Captains of the big boats would let off steam by challenging each other to a race to Guadeloupe and back. From those informal races, Antigua Sailing Week was created and in those days all of the yachts were what we would now call classic yachts. The first Antigua Sailing Week took place in 1967 over the 57 years ago. At first the classics held their own but over time they were outnumbered by the faster, sleeker modern racing yachts.

In 1987 two locally based big boat shippers had a rum or three and decided that their hard to manoeuvre full-keeled vessels need to race against each other on a level playing field. the Antigua Classic Yacht Regatta was born.

In 1991, Elizabeth Meyer brought her newly refitted J Class Endeavour and Baron Edmond Rothschild brought his 6-metre Spirit of St Kitts and the die was cast!

Antigua Sailing Week 26th April to 3rd of May
Seeking to extend the winter season by getting people to stay in Antigua a little longer a group of hoteliers sponsored the very first Antigua Sailing Week in 1968. Invitations were extended far and wide via travel agents, inviting everyone to come to the ‘Island for All Seasons’ – Antigua. Held in June that year participating boats came from the United States, Canada, and the Caribbean.

Festivities included a three-day ‘Lord Nelson Regatta’ with sailing yachts of up to 135-feet in length, power boat races, deep sea fishing and Sunfish sailing contests. There was also a two-day race among Antigua’s workboat fishermen whose boats had been freshly painted in bold Caribbean colours specifically for the event.

The inaugural Antigua Sailing Week was a success was repeated the following year. The dates eventually changed, and it became tradition for Antigua Sailing Week to officially begin on the last Sunday in April every year. Eventually the hotels became less involved, the workboat races disappeared, and dinghy racing events are now held separately. Race week is very much an important part of the sailing scene in Antigua and in 2024 it runs from the 26th April until the 3rd of May.