Every season, the best of the best from Europe, North America and beyond converge in the Caribbean for a healthy mix of sun, sailing, racing and fun across the region. The annual pilgrimage begins as soon as November for some, while the rest trickle in throughout the holidays and by February the season is in full force.

Whether you are crew aboard a maxi yacht or a full-on liveaboard considering the Caribbean circuit, there is something for everyone in the Caribbean.

Itinerary 1:
The Cruiser’s Rally and Races

Cruisers can find their way to the Caribbean fairly easily from Europe, despite the massive Atlantic Ocean that separates these iconic sailing regions. The Atlantic Rally for Cruisers helps bring over 200 boats annually to the Caribbean, many crossing the Atlantic for the first time, with others on their annual migration to warmer waters. Some cruisers never leave. Many of the liveaboard cruisers who are lucky enough to live in the lower latitudes head further south for the annual hurricane season and select Grenada, which is well-equipped and out of the storm path, for their summer season. Thus it’s easy for them to get right back into racing with the first international regatta of the year confirmed to be Grenada Sailing Week in January 2024.

Guy Chester, who sailed his trimaran Ocean’s Tribute all the way from Australia last season, enjoyed the Caribbean circuit so much that he decided to stay and do it all again in 2024. For cruisersturned- racers there is a plethora of event options and plenty of time to make their way to their next island or event of their choosing.

The St Maarten Heineken Regatta offers an Island Time class, which is designed for cruisers and those who want to have a more leisurely approach to racing. The Island Time class offers later starts, shorter courses and one race per day, so cruisers can properly balance their “Serious Fun!” time on the island – the regatta’s motto and commitment to a joyous event for all.

This was our first time doing the St Maarten Heineken Regatta and we’ll be back because we had a great time,’ says Heidi Herlihy, skipper of Swan 56 Tramontana who competed in the Island Time class. ‘There were some great competitors and people from everywhere, we made a lot of friends.’

The BVI Spring Regatta also offers a racing itinerary that is well suited for this race-life balance. This regatta has perfected the destination race with its Scrub Island Invitational. On the Wednesday of the sailing festival, competitors enjoy the morning sprint from Nanny Cay to Scrub Island where the fleet is greeted with an afternoon BBQ Pool Party. BVI Spring Regatta’s itinerary offers plenty of opportunities for racing and cruising, kicking off with the Round Tortola Race for a full tour of the surrounding islands with plenty of time to explore before and after racing events.

Continuing on at the end of April, Antigua Sailing Week has a “Club Class”, similar to the St Maarten Heineken Regatta’s Island Time class. These classes use the CSA Variable Simplified rating, with self-declared measurements and ratings adjusted daily depending on performance. This results in tighter racing as the week progresses, with more opportunities for all teams to experience the thrill of a podium position.

Itinerary 2:
Made for Maxis and Multis

While the Caribbean is a second home for many cruisers, with most of them now being multihulls, the region is also extending its warm hospitality to maxi racers.

The 10th Anniversary RORC Transatlantic Race will kick off January 2024. In recent years it has seen incredible growth since moving the start date from November to January. The RORC Transatlantic is the racer’s transatlantic choice and RORC’s enthusiasm in the Caribbean region has sparked the interest of more maxis year over year.

The International Maxi Association (IMA) took notice and established the IMA Caribbean Maxi Challenge in 2022. The trophy goes to the team scoring best two out of three of the Caribbean’s most competitive events: RORC Caribbean 600, St Maarten Heineken Regatta and Les Voiles de St Barth. The Volvo 70 I Love Poland, a Caribbean racing regular, was the inaugural trophy winner, though the maxis Deep Blue and Leopard 3 have contested in the past.

The St Barth’s Bucket is in a league of its own with a minimum LOA requirement of 100ft. St Barth’s is first-in-class, known for its luxurious amenities and entertainment offered to visitors. Even if you might not be lucky enough to receive an invitation to race, it is worth the trip during a regatta to experience just how grand the island’s hospitality can be. While such elite events can appear to be exclusive, the Bucket, among most regattas in 2023, supported their local youth sailing clubs.

Multihulls have also found a special place in the Caribbean with the Caribbean Multihull Challenge (CMC) launched in 2019, kicking off the multihull racing season at the start of February. In 2023 the event expanded with the launch of the CMC Rally for Cruisers where cruising catamarans sail in a funfilled three-day cruising event from Sint Maarten to Anguilla, then to French Saint-Martin and back to Simpson Bay. In 2024 the event continues to grow with a fourth day of racing added to the regatta.

The regattas on St Maarten, St Barth’s, and the Virgin Islands all use their islands’ unique geography, plus neighbouring rocks and other islands to offer a multitude of long coastal courses that stray from the traditional windward-leeward format. These events attract multihull cruisers and maxis alike for the long courses and ability to stretch their legs between marks — where naturemade marks are most favoured.

Itinerary 3:
The American Diehards

Lest we forget our compatriots from the United States who, despite a deceptively shorter journey “as the crow flies”, arguably have the most intense journey down to the Caribbean. There are essentially two options to get down from the east coast of America to the Caribbean by sail: The Thorny Path or the I-65.

The Thorny Path is near-shore, navigating from Florida through the Bahamas, flying by Turks and Caicos, skirting Puerto Rico and ultimately battling squally weather to beat around the Virgin Islands. The I-65 sounds simpler because it is: head east until you reach a longitude of 65 degrees west before turning south towards the Virgin Islands.

There is no shame in entering the Caribbean racing circuit half way through the season. There is plenty of racing still to be had with the double-header in the Virgin Islands starting at St Thomas International Regatta, celebrating 50 years in 2024, followed by the BVI Spring Regatta early April.

Nonetheless, American sailors have made the annual journey south for the winter for decades and more are pushing further south with their racing machines. In the 2023 St Maarten Heineken Regatta, an entire class of 50-60 footers were from the USA, where top US teams Hooligan (TP52) and Privateer (Cookson 50) got to battle it out for the first time in the Caribbean arena.

Not all teams are required to make the journey under their own keel. Many owners choose to ship their vessels down to the Caribbean. Some do this to avoid the wear and tear of an ocean crossing, while others do so to manage a packed racing schedule.

Cape 31 Flying Jenny raced in Key West, Florida less than a month before the team kicked off their racing season in the Caribbean in March with the St Maarten Heineken Regatta, St Thomas International Regatta and BVI Spring Regatta. Then the boat went back into its container and over to the UK where the team continued to compete at a high level for their summer circuit.

Port St Maarten, St Thomas and Antigua are all accessible, international ports that shipping companies such as Sevenstar and Peters & May service to bring yachts to and from the US and Europe. Many who ship choose to begin and end their season in Antigua with the RORC Nelson’s Cup to start, Antigua Sailing Week to finish and a whole lot of islands, regattas and parties in between.

For those sailing back home, the Antigua Bermuda Ocean Race returns in 2024 as a competitive option for the return route. East Coast US and Canadian boats as well as European teams will all route back home via Bermuda, often right after Antigua Sailing Week ends the regatta season. So why not finish the Caribbean racing season with an ocean race?

Itinerary 4:
CYOB - Charter Your Own Boat

Nothing goes to windward quite like a 747! Plenty of sailors choose to fly in and charter a local boat to get all of the best of the Caribbean with none of the hassle.

The Caribbean Sailing Association (CSA) and the member regattas offer great support and resources for first-time Caribbean sailors. You can explore a selection of reputable yacht charters on their respective websites and choose from race charters, bareboat, or individual berths. Race charters of 24ft trimarans, performance 40-footers, all the way up to professionally crewed Volvo Ocean Race boats and beyond are on offer through agents like LV Yachting. Bareboat charters are available from Sunsail and Dream Yacht Charter, and are in high demand for St Maarten, BVI and Antigua Sailing Week. Every regatta has its own offering, fleet and onshore amenities that can suit families, groups of friends or business colleagues.

No matter the boat or crew size, or your starting or end destination, the Caribbean Sailing Association’s packed event calendar should absolutely be included in your winter sailing itinerary.