It came down to the wire on the last day for winners in three of six classes at the International Rolex Regatta, which kicked off on Friday and hosted 68 yachts as well as more than 500 sailors representing the USA, Great Britain, Puerto Rico, Canada, The Netherlands, Russia, Italy, Sweden, Monaco and multiple Caribbean islands.

Fleet sailing last day's Pillsbury Sound courses - Photo by Rolex/Ingrid Abery

The event, in its 39th year and hosted by St. Thomas Yacht Club in the USVI, is the oldest regatta in Rolex’s portfolio of global sailing events, and is considered the “Crown Jewel” of Caribbean regattas.

Today’s tactically demanding Pillsbury Sound races, with courses that wound through the cays of St. Thomas and St. John, decided winners in one IRC and three CSA classes as well as a Beach Cat class, while one-design IC 24s completed six short-course races in Jersey Bay to determine that class’s victor. The races were sailed in picture-perfect conditions, which included plenty of sunshine and 15-knot breezes, which made the overcast skies and intermittent rain showers that prevailed over the last two days but a distant memory.

Peter Cunningham’s (George Town, CAY) 52-foot PowerPlay took overall victory in IRC, where nine boats were competing, and won a Rolex Oyster Perpetual Submariner Chronometer as a prize for its excellent performance. The team’s main competition was Willem Wester’s (Breskens, Zeeland, NED) Grand Soleil 46 Antilope (steered by Belgian Olympian Philippe Bergmans) and Ashley Wolfe’s (Alberta, Canada) IRC 52 Mayhem, which finished second and third, respectively.

IRC winner POWERPLAY yacht - Photo by Rolex/Ingrid Abery

“We were head-to-head with Mayhem the whole regatta, which made it exciting,” said Cunningham, noting that Mayhem’s disqualification in the second race of the series (for a pre-start infraction) and the dismasting of Lord Irvine Laidlaw of Rothiemay’s (MON) IRC 52 Highland Fling XII were unfortunate. “We lost the first race today by one second to Mayhem and Antilope (who corrected out equally and posted 1.5 points each) to finished third. The sailing is so interesting here; you can’t relax even one second or it’s the difference between first and second.”

Volvo Ocean Race veteran Bouwe Bekking (NED), tactician aboard Antilope, was pleased with second, especially since Antilope is a heavier displacement boat than the others, and he conceded that the story might have been different had Mayhem not shown a DSQ in her score line. “They would have had a second in that race, so you can count back and see that they would have done that much better,” said Bekking, “but that’s yacht racing.”

The competition today was unusually close in CSA 1, where Andrea Scarabelli’s (Cole Bay, St. Maarten) Melges 24 Budget Marine/GILL managed to maintain the lead it had established on day one and kept yesterday. It was by a mere half point in final regatta standings, however, that the team prevailed over Magnitude 400, a Farr 400 owned and skippered by Doug Baker (Long Beach, Calif.). The battle of the 40 footers, of which there were four in this class, had been billed as one to watch, but it quickly became clear that the Melges 24 came prepared to win.

The first day, Budget Marine/Gill posted two victories in the “town races” that featured plenty of downwind sailing. “This was good for us,” said the team’s tactician Christopher Marshall, “but the second day had lots of upwind sailing and that’s when it paid off for the bigger boats (Magnitude 400 won both races.). Then today was a mixed bag.”

Yachts SMILE AND WAVE and LAZY DOG battled for second and third in CSA 2, respectively - Photo by Rolex/Ingrid Abery

The half-point difference in the final scores was a result of Budget Marine/GILL’s third-place finish in today’s first race with the exact same corrected time as a second Farr 400 from California, Blade, so each boat was given 3.5 points as an average for third and fourth places (per the racing rules). “In the first start we were over early, so we had to come back and lost at least 30 seconds,” said Scarabelli, who drove. “Everyone was in a bit of a bad mood after that, because if it had not been for that, we would have probably been in second (for that race). We knew we had to do our best in the next race and maybe it would be impossible to win—that we could lose the Rolex regatta because of a half a point.” The team posted a third in the second race to Magnitude 400’s fifth, and that proved to be the combination that would give Budget Marine/GILL the final say and the coveted Rolex watch as prize.

Also winning by a mere half point today in CSA 2 was Jonathan Lipuscek’s (San Juan, PR) J/105 Dark Star. Lipuscek had gone into today’s races with a half-point advantage on the merit of two bullets posted yesterday, and he posted a 2-3 today to prevail over Jaime Torres’s (also San Juan) Beneteau First 40 Smile and Wave, also winning the a Rolex watch for his performance. Making it a triumvirate of Puerto Rican teams on the podium was Sergio Sagramoso’s (San Juan) J/122 Lazy Dog, in third, also with only a half point separating it from Smile and Wave. The three teams had been locked in battle for the entire regatta.

“We simply tried to minimize errors and do everything with patience,” said Lipuscek at the Rolex Awards party, which was held on the St. Thomas Yacht Club’s beach and featured a giant stage built out over the water. (It had been used on Saturday, as well, for the regatta’s headlining Reggae Concert.) “It’s incredible that we’ve won the watch; I didn’t believe it until now.”

Puerto Rican teams also finished top-three in IC 24s, which sported the largest fleet here with 15 boats. Dominating was Puerto Rico’s Fraito Lugo (Ponce), onboard Orion, who counts this as his ninth time to win a Rolex watch here. He passed the watch on to his foredeck crew Pablo Mendez and said that a full rotation has now been made as far as his crew getting to proudly share in the spoils of victory. “It’s experience in the boat,” said Fraito when asked what his secret to success was. “Pablo has been sailing with me since 2002, and my tactician and trimmer have been with me 18 years. It feels so good to win; we lost this regatta last year, so we came back this year very aggressive.”