6 ways to enjoy a regatta when you’ve never even been sailing

It only looks calm from here. Breathtakingly calm, but still. Photo: Craig/KTCpr

Even if your personal knowledge of sailing derives almost exclusively from “What About Bob?” and “Captain Ron,” you can still enjoy yourself thoroughly at a boat race. While (most of) the racers take their on-water time seriously, the vibe surrounding an event as historic and huge as the 35th Annual Heineken Regatta in St. Maarten is as exuberant and welcoming as they come. Here are a half-dozen ways for landlubbers to get the most out of one of sailing’s most storied competitions.

Learn the lingo

Photo: Shutterstock
“Ay, splice the mainbrace, matey!” Photo: Shutterstock

Spinnaker, jibe, boom vang, dousing socks: Sailing vernacular is colorful, to say the least, and hearing a crew chatter to one another about the day they’ve just had can be like listening to dialogue in an utterly, beautifully foreign language. Once you get the hang of a few basic terms, sprinkle them into conversation at your own risk. Just don’t go overboard (no pun intended) and veer off into International Talk Like a Pirate Day territory. (Or…do? Yes, do.)

Sail into the action

All lined up like ducks in a row. What a weekend!! #heinekenregatta #seriousfun #sailing #regatta

A photo posted by St.Maarten Heineken Regatta (@stmaartenheinekenregatta) on

If you can, book a spot on a pleasure or spectator boat in advance of the race and get an up-close-and-personal view of the regatta that you’ll never forget. (Aqua Mania Adventures is a great option, complete with stocked cooler, if you make it to St. Maarten.) It’s chaotic, potentially catastrophic, and totally badass to be up in the mix as hundreds of sailboats are duking it out on course. While you won’t be in any danger of taking a tumble overboard (unless you’ve sampled a bit too much of the local rum), you will get wet, so take a waterproof layer to ward off the ocean spray. You just haven’t lived until you’ve seen someone’s spinnaker shred itself in half within spitting distance of your seat.

Respect the sweat


A photo posted by @sailzone on

Wealthy men with sweaters tied over their polo shirts standing smarmily on deck while supermodels in bikinis lounge at their feet? While that image tends to prevail, sailing ain’t no pleasure cruise. It’s a highly physical endeavor wherein crews are constantly doing a bob and weave under the boom, rushing from one side of the boat to the other to keep the weight balanced when it’s heeling (which, to the untrained eye, looks like the thing’s about to capsize), and making imperceptible adjustments based on micro changes in wind and current. These sailors are athletes, indisputably.

Cheer for the boat with the best name

Simple, yet Odyssean. Photo of totally not-in-the-regatta boat: Shutterstock
Simple, yet Odyssean. Photo of totally-not-in-the-regatta boat: Shutterstock

No idea how the crews stack up against one another in the water? Then go amateur off-track betting style and decide by denomination. With names like “Kick ’em Jenny 2,” “Panic Attack,” “Pocket Rocket,” and “Aquaholics,” you’ve got plenty of contenders across the series. (Personal favorite toss-up at the 2015 Heineken Regatta? “Achilles’ Keel” v. “Team Zissou.”)

Mingle with the crews

We love it when the racers can race AND coordinate their outfits! #regattafashion #sailing #SeriousFun #sailingstagram #heinekenregatta

A photo posted by St.Maarten Heineken Regatta (@stmaartenheinekenregatta) on

Unlike marquee American professional sporting events, where there’s a hell of a firewall between spectator and athlete, races like the Heineken Regatta put you on the sand alongside a motley international mix of sailors. Regattas are, by design, a race wrapped in a party, so when the crews come ashore, they’re ready to participate in the land-based events too. Peopled by racers, locals, sailing enthusiasts, and top-tier musicians keeping everyone’s spirits up, the regatta parties are looked forward to all year, happen every night, and allow you access to the incredible talent propelling their boats toward a hopeful first-place finish.

Take the long view, too

so long, st. maarten. you’re a real babe. A photo posted by kstravs (@kstravs) on

While being in the water during a regatta is thrilling, the same scene observed from the beach is decidedly more serene. Be sure to spend some time just admiring the postcard-quality views of so many proud sailboats on the sea at once—preferably at sunset, with a rum punch in hand.

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