We’d slipped through the drawbridge at the entrance to Simpson Bay Lagoon on the southern shore of St. Maarten at the 1030 opening late last March, bound for the island of Dominica, some 170 nautical miles more or less due south. My old sailing buddy Hank Schmitt’s well-found Swan 48, Avocation, was headed for the second annual Yachting Festival in support of PAYS (Portsmouth Association for Yacht Security), a recently formed group dedicated to serving cruising sailors calling in the island. It sounded like a cool event, but what I was really savoring were the overnight sails to and from in the steady easterly trade winds. It had been a while since I’d spent a night at sea.

The derivation of the word “posh” is supposedly from British passengers who booked tickets for steamships bound for India. They were happy to pay a premium price for staterooms on the shady side of the vessel, which meant to port on the way over and to starboard on the way home (POSH: port out, starboard home). But the word also described our passage down the trades, a port tack (wind coming from the port side) heading south, and a starboard tack on the return trip to St. Maarten.

We were closehauled on the voyage south, and it was a bumpy ride, but there were some definite highlights. Off St. Barths, we caught a glimpse of the fleet of superyachts competing in the annual St. Barths Bucket regatta. At sunrise, we enjoyed a respite from the relentless easterlies, sluicing down the lee of Guadeloupe. The last 17 miles were sporty, but Dominica was straight ahead, the light at the end of the tunnel. Exactly 26 hours after passing through the bridge, we picked up a mooring in the coastal town of Portsmouth on Dominica’s northwest coastline.

It was a good, hard sail. The one back to St. Maarten a week later was even better.

As it was a relatively short passage, Hank did not set up a watch schedule, and I took the opportunity after our departure to hit a bunk for a few hours. I wanted to get the full night-sailing experience. And man, did I ever.

Read More from Herb McCormick: Reflections on Offshore Sailing

I popped up on deck at exactly midnight and was greeted by something I really didn’t expect: the Southern Cross, sitting pretty above our transom. Who knew it was visible in this part of the Caribbean? The moon had not yet risen, and the sky was brilliant, a virtual planetarium full of stars, including many a shooting one. It was mesmerizing. The rising of the three-quarter moon dimmed the light show a bit but was also magnificent.

We had to point a bit higher to skirt the windward side of Montserrat, but the wind had freed a little, and once around that volcanic isle, we were able to crack off a few degrees onto a powerful reach. I’d grabbed the wheel and was in no hurry to let go. The sailing was as good as it gets. The gusty trades fluctuated between 15 and 22 knots, the absolute sweet spot for a thoroughbred like Avocation. The boat was locked in at 8.5 knots of boatspeed, with the occasional burst over 9 and even 10 knots. We were definitely hauling the mail.

There’s never a better place to catch a sunrise than on the ocean, and with St. Kitts on the horizon, it was a pretty great one. We shaved a couple of hours off the trip on its return leg, and precisely 24 hours after departing Dominica, we dropped the anchor off Simpson Bay to await the next bridge opening, with plenty of time for a refreshing swim.

I’ll always recall with fondness the lush island of Dominica, but what I’ll really remember is sailing through those Caribbean nights.  

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It was the opening day of racing last February in the sixth annual Caribbean Multihull Challenge and Rally on the island of St. Maarten, and I was in the thick of the action aboard a 50-foot French catamaran charging upwind. At least I thought I was. A fleet of diminutive but extremely quick trimarans started to pass us, their three-person crews adorned in helmets with the spray flying. It sort of reminded me of the classic Western film Butch Cassidy and the Sundance Kid, where the protagonists are chased by a relentless posse and Butch asks Sundance, again and again, “Who are those guys?”

At the CMC, it turned out those dudes were sailing the fastest-growing one-design fleet in the islands, a nimble, blazingly quick 24-foot tri called a Diam 24. And man, they were having a blast. In an era when participation in sailboat racing is on the wane in many venues, the Diam 24 class on St. Maarten is an unqualified success story.

Built in France with infused fiberglass and a carbon-fiber core to a design by the VPLP naval architecture group—a consortium known for massive offshore trimarans such as the MOD 70—the Diam 24 is a small wonder that can be dismantled and shipped easily in a specially designed container. But the class owes its resounding popularity in St. Maarten to a singular, speed-obsessed French sailor named Pierre Altier, who skippers his own Diam 24 called Cry Baby.

After his first sail aboard the boat three years ago, Altier says: “I fell in love with this boat. Everyone says multihulls don’t go upwind that well, but the Diam points at a 45-degree angle at a speed of 14 knots, which is crazy for a boat this size.” In late 2021, Altier purchased Cry Baby and persuaded a couple of friends to join the fun, and all three boats were shipped to St. Maarten in a single container. The roots of success were planted.

But Altier, who runs a charter business in the islands, wanted more competition. He began lending the boat to friends and other local businesses to show them what it could do. “That was the key to get more people to join us,” he says. Before long, there were five Diams on the starting line for local events.

But Altier still wasn’t satisfied. He realized the numbers would grow if he owned several boats himself and chartered them out for regattas at reasonable rates, which is how the fleet grew to the 10 Diams racing in the CMC. At $700 a day for racing events, each of Altier’s three Diams is a bargain. Running rigging and a dolly for beach launching is $69,000 for a brand-new Diam with North Sails, which includes shipping to St. Maarten. In small-boat racing, it’s hard to imagine more bounce for the buck.

For Altier, there’s been only one drawback: For the first couple of years, nobody could touch Cry Baby on the racetrack. That’s no longer the case, as his fourth-place finish in the most recent CMC attests. “The competition has definitely ramped up,” he says. “I have a harder time than before to try and win. Better and better sailors were welcomed to come try and beat me, which is what happened.

“The word is getting out about how good the class is,” he adds. “And now we have multihull sailors from other classes coming to try out the Diam. It raises the level for everyone. For example, if you tune the boat better, we’re finding you can be 3 or 4 knots faster. It’s incredible. It’s been a real game-changer. And I’m very happy that the game is changing.”

So, Cry Baby is no longer the undisputed Diam 24 champion. Altier is spilling no tears.  

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Double the countries, double the fun in the sun in French Saint-Martin and Dutch St. Maarten. Enjoy the beautiful beaches, delectable dining and unique museums found on the twin sides of this tropical island getaway in the Leeward group of the Lesser Antilles.

Orient Bay Beach

Often called the St. Tropez of the Caribbean, this white-sand beach along the northeast coast of Saint-Martin is as well known for its turquoise waters and breathtaking scenery as for the clothing-optional section at its southern end. There’s a lively beach-bar scene, with venues serving French food and barbecue, and offering chairs and umbrellas for rental. Boaters seeking a less-sedated day at the beach can find adventure outfitters for parasailing, personal-watercraft rentals, tubing, snorkeling and other watersports.

Loterie Farm

Choose your own adventure at this 135-acre private nature preserve off the beaten path in Saint-Martin. Self-guided hikes along marked trails wind past mango and mahogany trees in the tropical forest en route to Pic du Paradis (Paradise Peak)—elevation about 1,400 feet—for views of the whole island as well as Anguilla, Saba and St. Eustatius. Adrenaline junkies can traverse the forest by zip-line, on runs as long as 1,600 feet. Many visitors opt to lounge by the jungle pool, strong cocktail in hand, or take in the views while dining in the Jungle Room.

Yoda Guy Movie Exhibit

British makeup and creature-effects designer Nick Maley is best known for helping bring Yoda, the wise and ancient Jedi master, to life for the original Star Wars trilogy. He now brings the series from a galaxy far, far away to St. Maarten in this fun and unique museum in Philipsburg. Visitors can see Yoda, Han Solo in carbonite, Darth Vader and more memorabilia from Star Wars and some of the other 50-plus movies that Maley worked on throughout his career. On days when The Force is with you, you might find Maley on-site, sharing his many behind-the-scenes stories.

Bistrot Caraibes

Opened in 1994, Bistrot Caraibes still shines brightly on the stellar foodie scene in Grand Case in Saint-Martin. It retains its standing as one of the best dining destinations on the island. Customers rave consistently and enthusiastically about this restaurant’s romantic atmosphere, top-notch service, well-curated wine list and fabulous French fare—especially the signature lobster thermidor.

Pineapple Pete/Wasabi Charlie

Just about everyone can find something to please their palate on the expansive menu at this casual, family-friendly dual venue in Philipsburg. It’s known for its attentive staff, friendly atmosphere and live music. Choose among sushi and steaks, pub grub and grilled seafood. There’s also a teppanyaki table during dinner hours.

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One glimpse of Roland Richardson’s plein-air paintings, and it’s clear why he’s known as the “father of Caribbean impressionism.” Just as Claude Monet memorialized haystacks and water lilies, the St. Martin native captures his home island’s fiery flamboyants (the national tree) and the soothing, surrounding turquoise seas.

When he launched his career on St. Martin in 1970 after studying art abroad, “no one else was addressing the people, the landscapes, the seas, the colors,” Richardson says. “I had an unlimited pure subject wherever I turned. I didn’t need to fabricate anything. I only needed to devote myself to observing with the intention of learning from it.”

With family roots on St. Martin that stretch back three centuries, Richardson has endeavored to preserve the island’s beauty and culture. He spearheaded the restoration of Fort Louis, overlooking Marigot Harbor, and documented the island’s history and architecture as the founding editor of Discover St. Martin-St. Maarten magazine. But it’s his artistic creations—be they in oil, watercolor or ink—that most resonate.

Visitors can find not only a gallery of his work at La Samanna Resort but also, sometimes, Richardson himself. He frequently hosts painting demonstrations where he philosophizes on light and color, and creates another of his signature scenes.

What makes St. Martin such an ideal outdoor studio? We’re in a region that, to a great degree, is still unpolluted. The light is pure, and the color is living and vivid and intense and joyous.  What are the challenges of painting en plein air? Engineering is one of the deep secrets of plein-air painting. You can’t pick up your brush and make that first stroke until you’ve solved how to set up and stabilize your canvas. That’s why most plein-air paintings are tiny; the size doesn’t pose a problem.

Recommendations for St. Martin

L’auberge Gourmande (Grand Case): We’ve known the owner, Pascal, for 30 years. He is a talented, award-winning restaurateur, and his team is amazing.

Mezza Luna (Nettle Bay): They have the most wonderful pizza and fresh, quality Italian dishes. It’s great value for the money.

The Lolos (Grand Case): These four restaurants are right on the water and have fresh fish, as well as ribs and chicken. The fresh snapper is my favorite. It’s a great local experience.

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