Can’t Miss Caribbean Sailboat Events in 2026
The Caribbean Sea is arguably the best sailing destination in the world. It has warm weather, champagne sailing conditions, and incredibly scenic places to drop anchor. It’s also home to some great sailboat events in 2026, making for a spring break or winter getaway.
Read about some of Go Sail Virgin Island’s favorite Caribbean sailboat events in 2026 and start planning your sailing vacation for next year!
BVI Spring Regatta & Sailing Festival
Located in the stunning British Virgin Islands, it’s no surprise that the BVI Spring Regatta & Sailing Festival is one of the best Caribbean sailboat shows each year. In March of 2026, the multi-day event still lives up to its reputation as one of the region’s premier events. Next year, in hopes that even more visitors will attend.
While the race around Tortola was previously the first event of the week, it’s now preceded by the more laid-back Scrub Island Invitational. This 12 nautical mile race is followed by a BBQ and pool party, where visitors can meet other sailors and chat with instructors about advanced ASA sailing courses that can help them compete in the race next year!
St. Maarten Heineken Regatta
When sailing industry professionals think of a sailboat event in the Caribbean, the St. Maarten Heineken Regatta is usually the first that comes to mind. No race in the area draws more sailors, and it’s been a popular event for 46 years. The 2026 schedule is from March 5th to the 8th, and, as always, will be all about “Serious Fun!”
The races include both coastal and windward-leeward, with different events for different skill levels. You can even participate in a more casual race on a liveaboard cruiser. At Go Sail VI, we charter many different bareboats that you can use to practice with in the Virgin Islands before the big event.
After the race, the parties in Regatta Village at Port de Plaisance are a blast, with live music, food, and a few Heinekens!
St. Barth’s Bucket Regatta
St. Barth’s Bucket Regatta began far from the Caribbean when 7 sailors raced their superyachts around Nantucket, Massachusetts. The name comes from the trophy (a discarded bucket), because the prize was sailing and the friends made along the way.
Now, St. Barth’s Bucket Regatta carries on this same tradition, with next year’s race happening on March 12 to 16, 2026. There are several race categories, including social (non-racing), Corinthian Spirit, 90-foot, and 100-foot boats.
Antigua Sailing Week
Sailors have been visiting the “Land of 365 Beaches” since 1968 to participate in Antigua Sailing Week. This year, the race is from Thursday, April 23 to Sunday, April 26. The event kicks off the day before with a welcome party, where you can meet sailing industry experts before the main events.
Each day has a point-to-point coastal race, with sailors dropping anchor and sleeping out on the Caribbean Sea at night. There are parties in the evenings, where you can take your dinghy onto the island and see why Antigua is one of the most exciting islands in the Caribbean.
Sail the Caribbean Sea in 2025/2026!
Peak sailing season is almost here, and sailors are already signing up for many of the best sailboat events. If you want to learn how to sail—or brush up on your racing skills—sign up for our ASA sailing courses before you plan your vacation around the best Caribbean sailboat events in 2026!