Sailing Events Embark Across Caribbean Waters in 2025

As befits a collection of islands blessed with year-around warm temperatures, Caribbean destinations maintain a treasured sailing tradition, as boat-making, sailing and the culture tied to seafaring are all part of the region’s past and present.

That tradition will continue throughout 2025 as countries around the Caribbean weigh anchor for a series of boat races, festivals and seagoing celebrations.

The British Virgin Islands (B.V.I.) Spring Regatta and Sailing Festival got underway earlier this month and continues through April 6. The event features seven days of “friendly and fun” yacht racing around the B.V.I., a locale long synonymous with island-hopping vacations.

The Regatta will feature 150 vessels from around the world racing across three-course areas. Bare boat, offshore multihull, gun boats and other large performance multihull vessels will participate in the week’s festivities.

As is standard for Caribbean sailing festivals, the event will also showcase local cuisine and offer travelers opportunities for community interaction, with farewell parties and barbecues planned to accompany the week’s boat races.

Later this spring travelers can venture south from the B.V.I. to the U.S. Virgin Islands, where the St. Croix International Regatta will take place on April 11 to 13 at the St. Croix Yacht Club.

Highlighted by three days of competition across the waters of Teague Bay, the regatta will offer multiple-class sailing, from cruising yachts to “one-design” vessels, racing through the Buck Island Channel’s unmatched scenery.

Evenings at St. Croix Yacht Club will showcase island cuisine and culture, with live Cruzan music, fire dancers, local seafood, a pig roast and rum punch specialties on the menu. Camaraderie between competitors and spectators makes the regatta “a must-attend social occasion,” in the words of the Caribbean Events website.

Further south, SVG Sailing Week in St. Vincent and the Grenadines (SVG) is scheduled for April 13 to 21. The event will blend sailing races with cultural immersion and authentic Vincentian cuisine at local gatherings pulsating with island music.

SVG Sailing Week’s multi-island format will showcase the archipelago’s most popular natural features, from St. Vincent’s volcanic landscapes to Mayreau’s hidden beaches.

Two individual regattas are planned: the Bougainvillea Cup (April 13 to 15), will navigate from the mainland through the Grenadines, with race legs to Union Island, Mayreau and Canouan.

Next, the Bequia Easter Regatta (April 16 to 21), will offer twin events: the Around Bequia Race and the Admiralty Bay Triangle. Following the racing, spectators and crew will gather to launch celebrations toasting Caribbean Sea waters.

Venturing north from SVG to the dual-island nation of Antigua and Barbuda, travelers can set sail for Antigua Sailing Week from April 26 to May 2.

Held annually at Nelson’s Dockyard, Antigua’s UNESCO World Heritage site, the event will feature international yachts, racing boats and performance cruising boats.

Spectators can observe the racing from the iconic Shirley Heights Lookout or opt for a “Chase the Race” catamaran excursion during the event’s five days of competition.

Celebrations and parties will take place throughout the week, including Dockyard Day, Reggae in the Park and the Lay Day Beach Party events.

In other Caribbean destinations, Dominica will be the starting point for Guadeloupe’s premier traditional sailing competition, Traditour 2025, on July 4.

The event will bring more than 400 sailors to Dominica to start the annual sailboat race to Guadeloupe. Anguilla will host a series of sailing events this summer.

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