The St. Thomas International Regatta has always been a multi-generational event, but the 51st event, held March 27-30, showcased a more subtle yet powerful aspect of that reality. The global sailing talent that this region has produced, coupled with the urge to “return home,” is creating a sailing juggernaut here, where international sailors can compete and hone their skills against some of the toughest competitors in the sport.

Such is the case for IC24 winner and St. Thomas resident Teddy Nicolosi, 23, a recent Yale University graduate who is an ICSA All-American and Academic All-Ivy sailor. Nicolosi pulled from his friends and family on the island to best the 21-strong fleet with a 29-point win after 15 races. His team was made up of fellow resident and two-time Olympian Tom Barrows, as well as SailGP U.S. team grinder Mac Agenese, who is married to Teddy Nicolosi’s sister, Graceann—herself an All-American former collegiate sailor. The team had plenty of competition against second-place finisher and champion sailor Marco Teixidor of Puerto Rico, who lost to them in the final race. Third place went to USVI Olympian and decorated sailor Cy Thompson with 47 points.
The IC24s were one of nearly 60 boats in six classes, ranging from one-design to Caribbean Sailing Association (CSA) handicap.

“During the final race, we knew we had a chance to win it, but there were only three points separating us from Marco,” Nicolosi said. “Our approach was to be calm, collected, and cool, and minimize the mistakes and focus on getting our speed up. On our team, it was amazing as we had the Olympic experience of Tom Barrows and the F50s of SailGP from Mac Agenese, so I learned a lot from them both when it came to managing the big breezes during these races.”
The event also featured 11 VX One sport boats, which were shipped to the islands by the fleet. Some of the best sailing action in recent memory took place among the top sailors, with VX One winner Sandy Askew battling it out against her husband, David Askew, who placed fifth. Sandy took home the top prize, with St. Croix native Tim Pitts finishing second.

Tim Pitts is credited with organizing 11 VX Ones to compete in this year’s regatta, and his dedication to the fleet paid off for sailors and spectators alike, as these fast sport boats were clocking over 25 knots as they completed their windward leeward courses. There were several capsizes among the three-person boats, but even in wind, waves, and strong currents, they were quickly righted and boats carried on.
“We are on the edge of control in these boats, and we can hit speeds that a lot of small dinghies cannot, but they are still dinghies and not an overly technical boat,” Pitts said, noting that he clocked 30 knots on his boat.

David Askew had longtime sailing friend Charlie Enright on board, who also sails with David on the TP52s. Enright is best known for being the skipper on the first American team to ever win The Ocean Race.
The VX One is a great addition to the fleet. The conditions are incredible here, and this level of racing creates some good old fashioned sailing fun,” Enright said. “There is also a really rich sailing tradition, and the talent that has come out of here is amazing. It is cool just to walk around the foyer of this yacht club and see the accomplishments of its members.”

With challenging conditions among all fleets, often the bigger boats can have more setbacks, and such was in the CSA and CSA non-spinnaker divisions. A dismasting, a collision, and other challenges knocked some teams out early, while the fleet also saw some stellar debut performances. The gorgeous, cold-molded, Brooklin Boat Yard-built 43-footer JAX, owned and helmed by Øivind Lorentzen, excelled. With St. Thomas native Anthony Kotoun on board as tactician, they came in second in their class, behind winning skipper Ryan Walsh on board is 52-foot Baltic Kinship.
“We had 27 knots of boatspeed (and we reached 30 knots)—you still have to consider that when racing in these conditions, navigating can be really tough,” Kotoun said. “We try to squeeze around a point of land or rocks while maintaining maximum speed,”

JAX owner Lorentzen was very pleased with the inaugural performance and plans to race the boat in the British Virgin Islands and then in Newport, Rhode Island, and at the Maine classic yacht circuits this summer.
“The boat held up beautifully and is entirely built out of wood, and is considered a modern classic, but our rating is such that it does hurt us a bit here because we are not really a cruising boat and not exactly an offshore sailing boat,” Lorentzen said. “However, I am particularly keen to support the wooden boatbuilding communities like the ones in Maine where some of the best work is being done today, and will be doing three regattas there this summer.”
In the CSA non-spinnaker class, Martin van Breems’ Jeanneau 409 Tatihou raced first, proving that cruising boats can have as much fun as hot rod racers.
“We had good starts and sailed well,” said van Breems, who owns the Sound Sailing Center in Norwalk, Connecticut, and sailed the St. Thomas International Regatta as the finale to his annual spring bareboat certification course. “It would be great to get more cruising boats out next year.”

Finally, in the nine-boat Hobie Wave Class, the United Kingdom’s Ian Bartlett won on Nuts/Bartlett. WINN finished second, with St. Thomas teens Finn Hodgins and Will Zimmerman, and High Tide Hooligans was third, with St. Thomas’ Mila Melbourne on the tiller.
St. Thomas Yacht Club Commodore Chris Rosenberg notes that the success of the regatta in coming years will be helped by the return of the younger generation who are now settling down here.
“In the IC24s, we had a record number of boats participating and really a sense of the younger generation taking their place here,” Rosenberg said. “Teddy Nicolosi is young, but he and the crew did put in the time to practice and get out on the water and seeing them out there doing Saturday afternoon racing in preparation for this has been great. As commodore, this regatta has been a great mix of great racing and fun.”
Laurie Fullerton is a writer based in Boston, Masschusetts. She has been a newspaper editor in the Boston-area, a sportswriter covering yacht racing, and a community reporter. She has been reporting for SAIL since 2017.