The St. Maarten Heineken Regatta is an iconic, bucket-list event in the Caribbean, and I’ve been fortunate to attend multiple times over in its 45-year history. I’ve been on race boats, chase boats, bareboats and multihulls and regardless of my ride, this thrilling competition in paradise has never ceased to delight me. But this year when I was shore-bound, stopping over in St. Maarten on a long layover, I gained a new perspective on this legendary Caribbean Race series. It was as much fun to watch, as it was to participate.

The St. Maarten Heineken Regatta was founded in 1980 with a dozen boats but has grown into a fleet of more than 100 to become the Caribbean’s queen of regattas. Thousands of crew, spectators and supporters come annually from local waters and abroad, representing a span of ages, genders and abilities. Four days of exhilarating competition and lively parties have kept the event true to its slogan of ”Serious Fun!” The action is all visible from dozens of magnificent vantage points around the 34-square-mile island.

This year’s regatta was held in early March and saw 107 entries from 30 different countries. Participants included smaller Sunfast 20s and Melges 24s to maxi Volvo Ocean racers, and a 20-boat bareboat fleet. 

Most races started off Simpson Bay or Cole Bay, with excellent viewing from the beach. One of the courses included a dash to Blowing Rock off Anguilla, sprinting past Maho Bay and the resorts there, while other divisions on the around-the-island course skimmed past Friar’s Bay Beach and Creole Rock, then blasted down the east side of the island past Orient Beach. 

The race committee positioned marks at Mullet Bay, and the mark roundings delivered an exhilarating spectacle for fans on the water and ashore. On Day 3 of racing the Diam 24 fleet of speedy, splashy trimarans competed in stadium-style racing directly in front of Tropics Beach Bar in Grand Case, with a start and finish line just meters off the beach, and live commentary from sailing pros. The half French, half Dutch island boasts 37 beaches on more than 43 miles of coastline. To miss the racing, you’d have to have your eyes closed.

Junior sailors racing neon RS Zests on Simpson Bay treated spectators to spills and thrills, while young adult sailors with disabilities could also be seen racing as part of the Sailability program. The regatta was truly an event for all sailors and spectators alike. 

Several of our friends booked spots on spectator boats. 

“It was so much fun watching from the comfort of a huge catamaran,” said Cindy Wynne, an avid racer from Southern California. “The captain was great at positioning our boat so we were able to see the starts, right at the pin end of the line, and afterwards motored to the windward mark to watch the spinnaker sets. Although we didn’t know any of the sailors, we cheered for them all as we enjoyed free Heinekens and rum drinks.” 

One morning we joined a score of spectators who had pulled off the road at Bell’s Lookout Point on Cole Bay Hill and enjoyed a bird’s eye view of the starts. Later we contented ourselves watching the races from the pool at La Vista Resort on Pelican Key. Then we strolled to the St. Maarten Yacht Club, where the daily post-race excitement is the afternoon drawbridge opening to Simpson Lagoon. Competitors put on a show for the mob at the club, who were well-lubricated with cold Heineken beer on tap. We saw sailors up the rig playing the guitar, dancing, imping, and even a proposal on the foredeck (she said yes). And if that wasn’t enough, epic nightly parties in the expansive Race Village at Port de Plaisance we free to all, with food and beverage trucks and live top-name entertainment.

OA friend from Colorado, Ed Kooij, with his wife Johanna, commented, “The atmosphere at the St. Maarten Yacht Club had been fabulous, watching all the participants coming through the bridge and passing the observation deck. But being on the water and watching the competition from the catamaran, with the beautiful weather and water, reignited my yacht racing itch! Now I am thinking, ‘We could get a team together, charter a boat and participate next year!’ It looks like a great venue for all participants.”

Book early Ed, bareboat charters fill fast. Next year’s St. Maarten Heineken Regatta will be held March 5 to 8, 2026. Visit www.heinekenregatta.com for more information