Three Sheets Regatta – An Epic Sailing Adventure @ 3 Days – February 19-22, 2026 – 3 U.S. Virgin Islands
A blast from the past – island-to-island distance racing – is now one of the hottest Caribbean sailing adventures of the present! The 5th Annual Three Sheets Regatta, set for February 19-22, 2026, delivers on this must-do experience with a stunning 100-nautical-mile sail from St. John to St. Croix and St. Thomas, in three separate legs that emphasize destination sailing rather than highly technical buoy racing. By day, the warm waters of the U.S. Virgin Islands offer steady breezes and challenging passages that suit experienced racers and adventurous cruisers, on their own boats or on a chartered vessel. In the afternoons and evenings, sailors move from St. John’s unspoiled landscapes to explore the heritage of St. Croix, before concluding in St. Thomas, where there are restaurants, nightlife, and a strong shoreside scene.
“What makes Three Sheets unique is its accessibility and spirit: open-water trade-wind sailing, strong yacht-club support on all three islands, and the ability to enjoy a true multi-island regatta. Plus, no passport required for U.S. citizens,” says Michael McCarty, director of the regatta, organized by the Virgin Islands Sailing Association (VISA). “For 2026, we are expanding charter-boat participation. As the regatta continues to grow as a destination event, it welcomes both locally owned boats and visiting sailors chartering in the U.S. Virgin Islands.”
Picture Yourself Under Sail!
St. Thomas’ Steve Schlosser’s 38’ Panda, Cranberry; Connecticut, USA’s Aaron Lathrop’s 57’ Custom Catamaran, Quest; and Texas, USA’s Michael Wilkinson’s 44’ Salon, Paroma, are among entrants of the 2026 Three Sheets Regatta.
“Unlike other regattas that are busy and full of 90-minute sprints, this is more laid back, and a chance to enjoy the three main USVI islands. The race is for fun, so you don’t have to worry about your bottom being the best, brand new sails, and a racing yacht, or about crew practices, new sails, and new rigging,” says Paroma’s Wilkinson. The party locations are great as well. Bring your friends and have a fun time!”
Bermuda High sailing in last years Three Sheets Regatta – Courtesy Three Sheets Regatta
The Route & The Revelry
The Three Sheets Regatta route pairs exhilarating distance racing with well-timed shoreside gatherings across the U.S. Virgin Islands. The event begins Thursday, February 19, from 5–8 p.m. in Cruz Bay, St. John, with registration and a relaxed opening social at The Saint. Friday’s race starts at 8 a.m. in Pillsbury Sound and sends the fleet south to St. Croix, finishing off Frederiksted and rolling straight into an easy beachfront mixer beginning at 4 p.m. at The Fred. Saturday brings the Two Towns Race, with a 9 a.m. start off Frederiksted and windward sail along St. Croix’s North Shore into Christiansted Harbor, followed by boardwalk time and an evening celebration beginning at 5 p.m. at St. Croix Yacht Club. On Sunday, competitors race north to St. Thomas, starting at 8 a.m. from the Buck Island Channel and ending at St. Thomas Yacht Club, where dockside festivities begin at 4 p.m. with the final of the nightly prizegivings.
Three perpetual prizes will recognize the fastest elapsed times across the regatta’s key courses: St. John to St. Croix, St. Croix to St. Thomas, and overall combined time. Current record holders are Wilkinson’s Paroma with 4:03:16 (2022) on the St. John–St. Croix leg; Frank Fenoglio’s Bermuda High at 4:24:47 (2024) from St. Croix to St. Thomas; and Warren Stryker’s Despacito with a combined regatta record of 9:06:07 (2023).
Enter Now!
For more information and entry, visit threesheetsvi.com. Entry fees are $150 for returning competitors who have previously sailed in the Three Sheets Regatta, and $200 for first-time participants. All entries and payments must be completed by February 19, 2026.
No boat? No problem. Charter from Waypoints Yacht Charters (waypoints.com/destinations/us-virgin-islands) and Charter Kai (www.charterkai.com).
Spectators are welcome at race finishes, dockside gatherings, and evening social events hosted at yacht clubs and local venues throughout the islands.
About VISA
The Virgin Islands Sailing Association serves as the official governing body for sailing in the U.S. Virgin Islands. Affiliated with World Sailing and the Virgin Islands Olympic Committee, VISA’s mission is to promote sailing within the local community, support competitive participation internationally, and offer educational programs for sailors and officials. VISA organizes races, supports Olympic and international competition, and advocates for sailors under the global standards of World Sailing.
virginislandssailingassociation.com
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