03/10/2026
New USVI Sailing Week Debuts April 8-11, 2027 – Race, Rally & Shop the Expo!
St. Thomas, U.S. Virgin Islands. Three of the U.S. Virgin Islands’ signature sailing and boating events come together April 8-11, 2027, for the first annual USVI Sailing Week at usvisailingweek.org. The St. Thomas International Regatta (STIR), Three Sheets Regatta & Rally, and Virgin Islands Boating Expo (VIBE) deliver four days of racing, island-to-island rally sailing, yacht shopping, demos, and shoreside fun across St. Thomas, St. John, and St. Croix. Nightly parties, prize-givings, live music, and drinks round out each day. It’s a fitting week of festivities for a destination Caribbean Journal named ‘Caribbean Yachting Destination of the Year’ in 2025.
“A highlight will be stadium-style IC24 racing off the Charlotte Amalie waterfront, putting spectators close to the action,” says Bobby Brooks, STIR co-director with Greer Scholes, and director of the St. Thomas Sailing Center. “Add VIBE at IGY’s Yacht Haven Grande, daily awards, and parties every night, and it’s a great way to showcase sailing and boating in the USVI. We’re grateful to the U.S. Virgin Islands Department of Tourism for its tremendous support.”
STIR: Tradition Meets What’s Next
Start with a lap around St. John. The $50-per-boat Round the Rocks Race kicks off Thursday, April 8, with an 11 a.m. first warning signal. Sail clockwise or counterclockwise around neighboring St. John, depending on conditions, with prizes afterward at St. Thomas Yacht Club (STYC). The best elapsed time around the full St. John course earns a perpetual trophy. Registration opens soon!
Steady trade winds, keen competition, and courses around the buoys and islands off St. Thomas are hallmarks of the 53rd St. Thomas International Regatta, April 9-11, 2027. Racing is open to CSA, ORC, and IRC boats, multihulls, bareboats, Class40s, IC24s, ISCAs, Hobie Waves, Wing Foilers, and accepted one-design classes. Registration will open soon!
Bring your own boat or charter. Sevenstar Yacht Transport and DYT Yacht Transport offer transportation between St. Thomas and the Mediterranean. Caribbean Regatta Logistics, (340) 998-6203 or [email protected], can assist.
For charter, the STSC offers IC24s and Hobie Waves, with wingfoil equipment available for rental. New for IC24 sailors is a 12-day, two-regatta charter package covering both BVI Spring Regatta (April 2-4) and STIR. The $6,800-per-boat package (valid March 31 – April 11) accommodates teams of four to five sailors, with STYC transporting the IC24s back to St. Thomas on April 5. BVI Spring Regatta-only charters are $3,900 and STIR-only charters $3,800. A $120 skipper membership fee and $2,500 damage deposit apply; regatta entry is additional. Charterers can race Round the Rocks or practice on April 8. stthomassailingcenter.com/racing/st-thomas-international-regatta
Sail Racing Academy (www.sailracingacademy.org) and LV Yachting (lvyachting.com) in the UK and Ondeck Sailing (www.ondecksailing.com) in Antigua also offer STIR 2027 race charters.
For more information, contact Regatta Co-Director Bobby Brooks at (340) 690-3681 or [email protected]. Follow STIR on Facebook at St. Thomas International Regatta and Instagram .
Three Sheets: Three Islands & 100 Nautical Miles
The Three Sheets Regatta & Rally combines island-to-island distance racing and cruising-style rallying, with roughly 100 nautical miles sailed in legs between St. John, St. Croix, and St. Thomas. Sail all the legs or just one. It starts April 8 with Round the Rocks around St. John, followed by legs to Christiansted, St. Croix; Charlotte Amalie and VIBE at IGY’s Yacht Haven Grande; and finally, STYC for the prize-giving. Parties and live music are planned at each nightly stop. Three Sheets registration will open soon.
No Boat? No Problem! Waypoints Yacht Charters (waypoints.com) is offering 10% off charter rates for visiting sailors who want to participate in the rally.
For more information, contact Regatta Co-Director Bobby Brooks at (340) 690-3681 or [email protected]. Follow on Facebook at Three Sheets Regatta, and Instagram .
VIBE: See It. Sea Trial It. Make It Yours
The Virgin Islands Boating Expo (VIBE), hosted by the Virgin Islands Professional Charter Association (VIPCA), brings sail and power yachts for sale and charter to IGY’s Yacht Haven Grande. Tour yachts, take demo sails and sea trials, browse marine gear and services, and explore diving, fishing, sailing, and other water sports.
For boat buyers, the USVI has no sales tax and offers duty-free allowances.
In partnership with VIPCA member vessels and businesses, VIBE attendees will have the opportunity to view the racing action and finishes on the water in Charlotte Amalie harbor. Shuttle transportation between Yacht Haven Grande and St. Thomas Yacht Club will make it easy to enjoy both events. For tickets, registration, and exhibitor and sponsor information, visit www.vibe.vi. Several St. Thomas hotels, resorts, and inns offer special VIBE rates, available on the same website.
For more information, contact (340) 642-0654 or [email protected]. Follow VIBE on Facebook at Virgin Islands Boating Expo and Instagram .usvi.
Getting to the USVI
St. Thomas offers nonstop service from numerous major U.S. gateways, plus regional Caribbean connections. Stay shoreside or afloat, with accommodations ranging from resorts, hotels, and inns to villas, timeshares, and charter yachts. For more information about the U.S. Virgin Islands, visit www.visitusvi.com
Photos Courtesy Ingrid Abery, Virgin Islands Boating Expo, Three Sheets Regatta
United States Virgin Islands
Caribbean Sailing Association
VIPCA - Virgin Islands Professional Charter Association
St. Thomas Yacht Club
US Sailing
Salty Dawg Sailing Association
Royal Ocean Racing Club
ARC Atlantic Rally for Cruisers
Waypoints Yacht Charters
