First Annual USVI Sailing Week April 8 – 11, 2027

Three Events, Three Islands, One Week: The First USVI Sailing Week Is Coming

Something new is coming to the U.S. Virgin Islands. From April 8-11, 2027, the St. Thomas International Regatta (STIR), the Three Sheets Regatta & Rally and the Virgin Islands Boating Expo (VIBE) come together as the first annual USVI Sailing Week (USVI-SW).

Over four days, sailors and boaters can enjoy 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 debut for a destination Caribbean Journal named Caribbean Yachting Destination of the Year in 2025.

Photo: One-Design IC24s offer highly competitive racing at the St. Thomas International Regatta (STIR). Credit: www.ingridabery.com

“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 U.S. Virgin Islands. We’re grateful to the U.S. Virgin Islands Department of Tourism for its tremendous support.”

The Week at a Glance

• Thursday, April 8: Round the Rocks Race around St. John opens the week for STIR and Three Sheets sailors
• Friday-Sunday, April 9-11: 53rd St. Thomas International Regatta
• April 8-11: Three Sheets Regatta & Rally legs between St. John, St. Croix and St. Thomas
• During the week: VIBE at IGY’s Yacht Haven Grande
• Every night: Parties, prize-givings and live music

Round the Rocks: April 8

Sailing Week starts with a lap around St. John. First warning signal is at 11 a.m., and the fleet will sail clockwise or counterclockwise depending on conditions. Prizes follow at St. Thomas Yacht Club (STYC), and the best elapsed time around the full course earns a perpetual trophy. Entry is $50 per boat.

STIR: Tradition Meets What’s Next

The 53rd St. Thomas International Regatta runs April 9-11 with the steady trade winds, keen competition, and courses around the buoys and islands off St. Thomas are hallmarks STIR is known for. 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!

The St. Thomas Sailing Center offers IC24 and Hobie Wave charters and wingfoil rentals. New this year for IC24 teams is a 12-day, two-regatta package covering BVI Spring Regatta (April 2-4) and STIR:

• Two-regatta package: $6,800 per boat, valid March 31 to April 11, for teams of four to five. STYC will transport the IC24s back to St. Thomas on April 5.
• BVI Spring Regatta only: $3,900
• STIR only: $3,800

A $120 skipper membership fee and $2,500 damage deposit apply, and regatta entry is separate. Charterers can race Round the Rocks or practice on April 8.

STIR 2027 race charters are also available through Sail Racing Academy and LV Yachting in the UK and Ondeck Sailing in Antigua. Bringing your own boat? Sevenstar Yacht Transport and DYT Yacht Transport ship between St. Thomas and the Mediterranean, and Caribbean Regatta Logistics can help at (340) 998-6203 or benbeer13@gmail.com.

Three Sheets: Three Islands and 100 Nautical Miles

The Three Sheets Regatta & Rally mixes island-to-island distance racing with cruising-style rallying over roughly 100 nautical miles. After Round the Rocks, legs run to Christiansted, St. Croix; to Charlotte Amalie and VIBE at Yacht Haven Grande; and finally to STYC for the prize-giving. There’s a party with live music at every stop. Sail all the legs or just one.

No boat? Waypoints Yacht Charters is offering 10% off charter rates for visiting sailors joining the rally.

For more information, contact Regatta Co-Director Bobby Brooks at (340) 690-3681 or director@stthomassailingcenter.com. Follow on Facebook at Three Sheets Regatta, and Instagram @threesheetsregatta.