Anguilla, St. Martin and St. Barts - The Caribbean’s 3-Ring Circus

The islands of the Caribbean divide into neat groups of cruising territories. It’s as if they were doled out like cookie batter on a baking sheet of azure waters.

Some of these clusters, like the British Virgin Islands and St. Vincent and the Grenadines, can have a certain homogeneity. Other groups, like St. Martin and its neighbors Anguilla and St. Barts, are bursting with diversity. Although within half a day’s sail of one another, these islands differ in language, customs, approach to yachting and even the daily pace. But their signature flavor is definitively Caribbean.

St. Martin also St. Maarten

You may board a plane that is headed to St. Martin, but you’ll land in Sint Maarten. The first spelling is French and the second is Dutch. Princess Juliana International Airport is on the Dutch side with its glide path over the world-famous Maho Beach, where jets graze the heads of tourists snapping photos and getting pummeled by sand. The spot is so popular that bars have grown around it, with crowds watching the air traffic for hours. The airport was seriously damaged in Hurricane Irma, but the island is recovering and it is open for business.

The French side makes up a bit over half of the island’s total 38-square-mile landmass. Superyachts dot Simpson Bay, having squeezed through the southern drawbridge that’s barely wider than their beam.

Three cultures live in harmony (Dutch, French and West Indies) with no visible borders to cross and with English as the common language. The staff of the various charter companies is a mix of Dutch and French expats and locals. They’re friendly, efficient and offer excellent chart briefings. Tips on how and where to check-in and out at various ports are especially helpful because these procedures must be taken seriously here. Once you are done with officialdom, you can sit back and take in a sunset from one of the dozens of locations.

The Sands of Anquilla

In just a couple of hours, you can sail around the western end of Anguilla and up to Road Bay on the northern side. A large and quiet anchorage is the first port of entry to the British Overseas Territory, which has a distinctly different vibe from St. Martin. The island is low-lying and dotted with mostly modest homes. The trinket boutiques are few and the cruisers are the real deal with boats that look like they’ve gone the distance. There’s very little glitter, but a lot of charm.

Anguilla is all about the natural beauty of the tropical beach. It’s the stuff of escapist postcards. Sandy Island and Prickly Pear Cays top the list of must-sees. If you want to experience Sandy Island in relative calm and without crowds, arrive early before the only bar on the island opens. The cruising guide map of the surrounding reef is a bit confusing, so don’t be surprised if you miss the dinghy pass entirely.

After lounging a bit on the powdery white sand and maybe enjoying a cocktail, sail for Prickly Pear Cays less than five miles to the north. From the southern anchorage, the cays don’t seem to have much to recommend them until you dinghy around to the northern beaches and the crystalline water.

If you arrive later in the afternoon, the day boats from the local resorts will be in the process of picking up their tourists and leaving, which means you’ll enjoy the beaches and Prickly Pear Bar in relative peace. With sturdy reef shoes, you can amble along the moonscape of dead coral that makes up the western end of Prickly Pear East and check out the ground-nesting birds. Mother boobies stand sentry over their white fluffy offspring, so unafraid that they barely register as you pass within a few feet.

St. Barthelemy (aka St. Barts or St. Barths)

Switching from a castaway paradise to the glitz of international yachting, set course for St. Barts. This is a mecca for competitive sailors with high-profile races like the St. Barts Bucket and Les Voiles de St. Barths, where superyachts gather to race and/or spectate.

Gustavia is the main port with a snug harbor that’s surrounded by historic houses topped by red-tiled roofs. In the spring, the small streets are packed with the glamorous set. Modern shops coexist with old fortifications, which is evidence of rich history when the French, British, and Swedish all made and lost fortunes here going back to the 1600s.

Chic restaurants with French haute cuisine offer views of the yachts in the harbor while boutiques with designer wear, fine jewelry, and watches lure shoppers with discriminating tastes. Spa service providers and gourmet provisioning stores cater to a superyacht clientele and advertisements for just about every kind of luxury brand meet you on every corner.

Rent a car for an up-close look at the hotels and residences that hover on the hillsides overlooking hidden beaches. St. Barts has been called the “Riviera of the Caribbean.”

If St. Martin has the most unusual airport for big jets, St. Barts wins the prize for the most demanding airstrip for commuter planes. Standing at the top of the saddle between two hills, you almost have to duck as each small aircraft drops in over your head onto the runway below. This strange thrill attracts crowds as people pull their cars over and run to the intersection to experience the whoosh of air as the planes wiggle, roar and generally butterfly their way to safe landings. When you’ve had enough of the glitz and glamour, head up to Anse Colombier to join other cruisers in a large and picturesque anchorage.

Rounding Back up To St. Martin

Word has it that checking back into St. Martin via Marigot is difficult but going via Anse Marcel, a short motor up the coast, is a breeze. The marina there is full of colorful iguanas lazing about the docks looking for a handout and posing for their close-ups.

Once checked in, slip back down to your last anchorage of the week, Marigot, with its pastry shops and Plein air market where artists hawk everything from spices to intricate tagua palm nut carvings also called “vegetable ivory."

Three islands, three languages, a dozen bays, and one boat is a St. Martin adventure by the numbers. It’s about the sunsets, the color of the sand and the smiles of carnival dancers. It’s about exploring a self-contained corner of the Caribbean where short hops lead to lots of diverse adventuring.