There are more than a few sailors who will remember Day 2 of the St. Maarten Heineken Regatta as being one of the longest days of racing they’ve ever had. All but the bareboat classes sailed two races; the first a 26-mile course that took the fleet to the French side of the island and the Anguilla Channel, the second a 14-mile (22-miles for the big multis and Spinnaker 1) endurance marathon in a dying breeze. The Anguilla Channel turned into a parking lot, and many boats, including the entire class of Spinnaker Racing 6, and many of the bareboat classes failed to cross the finish line before the time limit expired at 6 p.m. The forecast was for a breeze that would start from the southeast and clock due south and die, and it was spot-on. The start of Race 1 for all classes was between Simpson Bay and Philipsburg, which led to some interesting conversations between boats that had already started, and bareboats that were streaming out of Philipsburg-the location of Friday night’s regatta party. On the Swan 45 Plenty, racing in Spinnaker 2, it was a spectacular start to the day as we led around the first two marks. Leveraging that good start into a win required some gutsy tactical calls, lots of jibes into the beach looking for breeze on the second leg, and a bevy of sail changes as we made our way around the convoluted racecourse using every light-air headsail in our inventory, including the Code Zero. We were able to stick close to the fastest-rated boats in our class, the Swan 56 Hissar and the R/P 43 Storm, and ahead of our closest competition, the other Swan 45 in our class, Vixen, to take our second win. Vixen took second, and Caccia alla Volpe, third. The third race of the regatta started out looking ugly for Team Plenty. It was a downwind start and off the line we were buried below most of the rest of the class, which forced us to jibe away for clean air. Halfway down the first leg, we were deep, with Storm, Hissar, and Vixen all crossing well ahead. As the wind died passing lanes became nonexistent, and the race started looking like a parade. Hissar was launched, and Vixen and Storm weren’t far behind, but on one of the final roundings, Storm had issues getting their spinnaker down and sailed off the course. We finally got close enough to Vixen to initiate a light-air, roll-tacking duel that had us looking good until a lift levered Vixen well ahead once again. On the next-to-last downwind leg, it looked as though Vixen was going to beat us soundly, until they decided to jibe away and look for more breeze out in the channel. We stayed closer to shore, ended up with more wind, and by the next time we crossed jibes, we were well ahead with two legs to go. Our emotions were mixed. We were happy about getting ahead of Vixen but sympathized with its crew. We ended up second in the race behind Hissar, which put us in great shape for the final race on Sunday with a 1-1-2 scoreline, three points ahead of Vixen. In Spinnaker 1, where the big boys play, it’s all about local talent. Tom Hill’s Titan 12, a fixture in the Caribbean Big Boat Series, has beaten Joe Dockery’s Carrera in two out of three races. Carrera came back to win the last race of the day, but will have to work hard to top Titan. American sailors are doing well in the bareboat classes, with Bruce Ogden on top of Bareboat 2, and Mark Duranty in the lead in Bareboat 3. The final race of the Heineken Regatta is Sunday, and for us, the big multis, and Spinnaker 1, it’s a 29-miler. The forecast calls for another day of atypically light winds, which means there’ll be plenty of opportunities for us to either do well, or end up deep. We’re hoping it’s the former. No matter where one ends up at this year’s Heineken, the party afterwards should be a great way to end the series. Reggae legend Jimmy Cliff will be playing, the drinks will be flowing, and it all beats the heck out of shoveling snow.