“There were nine of us who had never raced together, and we all had various levels of experience. We shrimped the spinnaker in one race,” Weinstein said. “But sailing in 18 knots around the various race courses was a great challenge. You can’t top the world-class racing.”

For other sailors without a boat or a crew, the head-boat option, where sailors pay per person to race as part of a program, is growing increasingly popular. This year’s event saw the return of the Volvo 65s and 70s, which were spending the winter in the islands waiting to compete in the last legs of the Ocean Race later in spring. The teams were made up of a mix of professional crew and pay-to-race sailors. 

“My original ride for the regatta fell through, so I thought what the heck and signed up to race on the Volvo 70 Hyper,” said David Spaur, who races out of Monterey, California. “It wasn’t as exciting as I hoped. The sailing is beautiful here, but they only let us grind and sit on the rail.”

That wasn’t the case aboard Avocation, where the sailors switched between positions. Schmitt owns and operates Offshore Passage Opportunities based on Long Island, New York. The company offers a mix of learn-to-sail options, including a week in St. Maarten, and he has long played a big role through the years in bringing sailors and boats down to the Caribbean through his cruiser rallies and crew placement programs. For the St. Maarten Regatta, Avocation’s crew organized their own flights and paid around $2,000 plus food depending if they stayed in the villa or aboard the boat.

“We were looking to get more experience and confidence to sail our own boat on longer passages,” said Jens Daum, who along with her husband Alja, own the Beneteau Oceanis Teagan in Oyster Bay, New York. “This has been a great experience with Hank. He really takes the time to do it right.”

The race committee had sent those of us in the Island Time class and the bareboat classes on a course along the leeward shore to avoid the stronger winds on the windward side of the island, where the main racing fleet was sailing. On the upwind leg, the concentration aboard the boat was high as we searched for the mark off Marigot Bay. 

“After the mark the rail crew come on back and take over the trimming,” Schmitt said. “Keep an eye out for the mark.”

The crew talked through the maneuvers and the rounding, and the rest of the race went off without a hitch. Motoring back into Simpson Bay after the race, the crew waved to the folks packing the deck of the Sint Martin Y.C., and began making plans for their outfits for the Bridge Show on the final day. We ended up in second place for the day, and the crew went on to finish in fourth place for the regatta with Ferron’s Bunglebird taking first, but it wasn’t just about the trophies.

“We couldn’t have asked for a better time to be sailing and learning,” Daum said. “Alja and I had a blast sailing all day, followed by a quick swim back at the villa before heading to the party at night. The Heineken is seriously fun.” 

For more information, visit www.heinekenregatta.com.