Keeping the America’s Cup Spirit Alive on St. Maarten

Sailing a retired racing yacht in the 12 Metre Regatta, Tim Harper finds himself in a tense competition with the legendary vessel Stars & Stripes.


Retired racing yachts race in the St Maarten 12 Metre regatta. Photo © St Maarten 12 Metre Regatta

It’s a good day for sailing off St. Maarten, one of the Leeward Islands in the northeast Caribbean – sunny and 80°F (26°C), with a fresh breeze. I join the crowd of travelers on the main pier at the capital city, Philipsburg.

I have sailed a bit, but most of us are non-sailors who’ve heard about the St. Maarten 12 Metre Regatta – essentially a mini-version of the America’s Cup races that have long captivated an audience beyond hardcore sailors. The 12 Metre has won many awards for being one of the best “soft adventures” in the Caribbean. But it wasn’t so soft for some of us.

Learning to sail a 12-metre yacht

A handful of 12 Metre staffers work the crowd, dividing us into two crews of 15, with comparable numbers of young adults, older people, and children. Each crew boards a launch and is ferried to its yacht. My group steps onto True North IV.

The yacht’s tanned young captain spots my triathlon t-shirt and assigns me the most physically demanding job on the boat, one of four “grinders,” furiously cranking lines in and out on big spools as the sails are re-set.

Two other professional crew, equally young and tanned, give orders to the rest of us. Everyone has a task – one elderly lady was named timekeeper – and we realize it’s up to us to sail this very fast boat.

Which is no easy job. The 12-metre yachts, historically “the greyhounds of the sea,” are beautifully sleek but finicky vessels built for speed, not comfort, nearly 70ft (21m) long with an 86ft (26m) mast, weighing 35 tons (31,750kg) and flying 1,700ft2 (158m2) of sail. (The “12 metre” classification comes not from the yacht’s length, but from an equation based on several measurements, including the distance from deck to water.)

The 12s were the official boat of the America’s Cup until 1987, when the sports world was riveted by the dramatic races off Fremantle, Australia that resulted in a victory by the New York Yacht Club’s entry, Stars & Stripes, arguably the most famous racing yacht in history. For the 1988 Cup, the specifications were changed, and the future of the 12-metre yachts dimmed.

Ivy, as our crew call our boat, was one of five 12s rescued by the St. Maarten outfitters and brought to the Caribbean to do what they were built to do: race.

After more than an hour, we ragtag visitors feel like a real crew. It’s time to race the other 12, which has been zig-zagging across the harbor, training its crew, too. The course is five legs of about 1mi (1.6km) each, compared with the typical 22m (35km) America’s Cup race.

Another of the 12-metre yachts sailing off St. Maarten. Image credit: Getty Images / Teacherdad48

Racing against an America's Cup legend

As the yachts maneuver toward the starting line, the other 12 comes close enough to glimpse its name.

Astonished, I look at the captain. “Is that…?” I ask.

“Yeah,” he says. “That’s Stars & Stripes.”

We help our timekeeper count down, and swoosh across the starting line seconds ahead of Stars & Stripes.

After one tack (turn into the wind) about 30 minutes into the race, our captain frowns. “We’re behind,” he says. “They’ve positioned themselves to take our wind.” We can catch up only with a series of sharp tacks. “It’s a lot more work,” he warns us grinders.

The next 10 minutes are a mix of concentration and perspiration as True North IV sweeps back and forth. In a decisive move, the yachts appear to be headed toward the same spot on the water from sharply opposing angles.

Heeling at 15°, salt spray in our faces, our boat moving so fast we can hear the bow slicing through the waves, we cut in front of Stars & Stripes at a right angle, almost close enough to reach out and touch its bow.

The good-natured jeers from Stars & Stripes fade as we move away. Another quick tack, and we glide across the finish line, half a length ahead.

“We did it,” the skipper exults. “A slam dunk.” Our shipmates raise a round of cheers for us grinders. I close my eyes, savoring the sea and sun. When I open them, the young skipper is smiling at me. “Hey,” he says quietly. “We just beat Stars & Stripes.”

Trip Notes

The St. Maarten 12-Metre Regatta is based on the main pier at Philipsburg, near Bobby’s Marina, and at

Races begin at 8:30am most days, and continue through the day with up to four additional races, depending on demand, at 10am, 11:30am, 1pm, and 2pm.

The cost is US $90 for adults, and US $65 for children 9 and older. Reservations through the website are recommended, but walkups on the pier will be accommodated if there’s room. The yachts have undergone minor renovations for safety, but not comfort. There is no head (bathroom) on board. People with disabilities should inquire about accessibility.

The typical race experiences takes two to two and a half hours, not counting a complimentary rum punch afterward in the 12 Metre Regatta’s club house.

Note: Sailing can be a dangerous sport. Wear your safety equipment including a life vest, don’t mix sailing with alcohol or drugs, and stay aware at all times of your surrounds and the changing weather. Check your travel insurance policy for more details.

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