St Martin
St Martin

A Triple Dose of Caribbean Heaven

Renowned resorts, cuisine, and beaches abound in the elite island cluster of St. Martin/Sint Maarten, Anguilla, and St. Barts.

The islands of the Caribbean are complex, in terms of positioning and nationality. When you want to go island-hopping in Spain, you can easily pick out the Balearic islands on a map; likewise, Greece’s various clusters (Cyclades, Ionian, Dodecanese) are easy to discern, as are French Polynesia’s. But most of the 700 or so islands (including around two dozen major ones), isles, and cays of the Caribbean Sea aren’t laid out in tight little geographic and national groupings.

Though the Caribbean archipelago is divided between the Leeward, Windward, and isolated islands of the Lesser Antilles (as well as the Leeward Antilles off the Venezuelan coast), from above, the semicircular chain looks barely interrupted. And these sun-blessed dots on a map represent a spate of independent countries and dependent territories, making things even more complicated. 

To simplify matters, you’d do well to zero in on St. Martin/Sint Maarten, Anguilla, and St. Barts, which lie near the middle of the string of islands. They are so close together—and share such an elevated reputation for fine gastronomy and stunning sandy beaches—that it would be worthwhile to organize a trip around the three. 

With all three islands falling within the hurricane belt (storm season is June through November), the high season runs from December to April, with various peaks and slight lulls in tourism. During the Christmas holidays, the most revered hotels are so in demand that some people make reservations a year in advance, with certain well-heeled families maintaining standing reservations through the years—or even decades. (The holiday popularity means that you may be able to snap up a reservation at a top hotel or villa earlier in December and during the immediate post–New Year’s period.) That said, summers are popular with European travelers and can be lively, with the sea breezes offsetting the humidity. Many hotels shut down in September or October to avoid weather issues and to freshen up for the high season. 

French St. Martin shares a hilly, verdant, and comparatively developed island with Dutch Sint Maarten, which occupies the smaller southern part. The island, which has a population of around 70,000, rests between Anguilla (which is nine miles to the north) and St. Barts (17 miles to the south). Anguilla and St. Barts are smaller and quieter; the former is home to around 15,000 residents, while the latter has around 10,000. 

St. Martin Boasts Extraordinary Beaches

Though Anguilla and St. Barts enjoy a more upscale ambiance overall, what makes St. Martin/Sint Maarten enjoyable are its 37 beaches, which account for a range of tropical experiences; at least one top-tier luxury resort; and its fine cuisine. The beaches are extraordinary thanks to their powdery white sands and arresting shades of cyan water; there are both action-packed and serene beach options, long crescents, and cunning coves. 

A perfect sandy arc, at a bit less than two miles long, Orient Bay Beach is the island’s most illustrious site, for good reason. Located in the northeast on the French side, it is long enough, with enough diversions, to keep you occupied for days. It has a French, somewhat risqué flavor, as it becomes increasingly clothing-optional as you meander south. Along the way, you’ll find many restaurants and beach clubs where charming servers offer up bottles of rosé in Champagne buckets delivered to your beach lounger or to a wooden table set up right on the sand. Among the beach bars where you can enjoy lunch are Kontiki, Wai Beach, and Bikini Beach. Compared with the atmosphere at many other Caribbean islands, the Saint-Tropez-inspired Orient Bay feels sophisticated, and the beach clubs are well-designed.

Orient beach in St Martin
Orient beach in St Martin

Kontiki, with music supplied by a DJ, has been around since 1989, and its brilliant red umbrellas and chairs telegraph the place as something of a casual landmark. Kontiki was the first restaurant on Orient Bay; others followed, including Wai Beach, which serves up a fine lobster millefeuille with mango, avocado, and wonton chips. The handful of clubs are well-distributed, so the ample beach never feels overcrowded. Even with the jet-skiers, this enviable spot retains an air of exclusivity, but without attitude. 

Orient Bay is one of the most pleasurable beaches in the world, but 36 more great ones are nearby. If you’re driving, you can hug the coastal road—in an hour, without stopping, you can see most of the island—and pull to the side wherever you spot a stretch of sand. Locals are especially fond of Friar’s Bay, a smallish cove with lovely foliage and a castaway feeling; it’s also admired for its ring of good restaurants. Red Bay, also on the French side, is undeveloped and offers some of the island’s best swimming spots. 

The Dutch side boasts pristine Mullet Bay, which once fronted a popular resort. Though a hurricane destroyed its hotel in 1995 and the adjacent golf course doesn’t garner rave reviews, the beach is long, calm, and beautiful. Nearby Maho Beach rests under the path of incoming airplanes, so it’s the site of countless Instagram photos; the rollicking scene is not for everyone, even though the water is gorgeous. In the same vicinity is the island’s most uncharacteristic beach, Cupecoy, a series of small, secluded coves backed by dramatic limestone cliffs.

Charming Marigot is the capital of the French side, and with many of its bistros set around a marina, it’s a fine place to stroll around and pick up a pair of sunglasses, a glace (ice cream) cone, or a baguette or croissant (you can’t go wrong at La Suciere, which is part pâtisserie, part boulangerie). Foodies favor the cozy strip of two dozen restaurants at Grand Case, which is right on the sea. There’s not much sand, but you can enjoy a dip.

Shoal Bay West, Anguilla Island
Shoal Bay West, Anguilla Island

Golden Sands in Aguilla, Stars in St. Barts

In contrast to hilly, green St. Martin, Anguilla is flat, dry, and low-lying. Skinny, at 16 miles long, this British Overseas Territory exudes bonhomie and a sense of safety. It is more manicured than St. Martin, featuring a handful of unforgettable resorts and stunning beaches. Savvy travelers know to spend at least a day on Maundays Bay, even if they’re not staying at the revered Cap Juluca, which sits on this flawless crescent. 

From there, you can easily beach hop on the southwestern part of the island; Rendezvous Bay, Shoal Bay West, and Cove Bay are nearby. Across the tip of the island, Meads Bay, in Anguilla’s northwest, draws a spirited crowd to its gorgeous golden sands and wave action; the beach sits beneath Blanchards restaurant, as well as several hotels, including Malliouhana, an island institution for 40 years that the Auberge brand now operates.

Gustavia, St Barts
Gustavia, St Barts

Finally, St. Barts, an overseas collectivity of France, is associated with glamour and exclusivity for good reason. Gustavia, its portside main town and capital, is widely regarded as the loveliest town in the entire Caribbean, characterized by its red-roofed buildings topping stylish boutiques and cafes. Located in the middle of the island’s east coast, Gustavia’s marina is regularly lined with the pleasure craft of the elite, and celebrities are often spotted. Though the island hosts several luxury hotels, many visitors prefer to rent a villa.

Exploring is simple, given St. Barts’s diminutive size. The closest beach to Gustavia—a five-minute walk—is Shell Beach, named as such because the “sand” is composed of crushed shells. This small cove is a favorite spot to admire the sunset. It takes less than 20 minutes to cross the island from Gustavia to the Rosewood Le Guanahani hotel, on the east coast. On the way is popular, palm-lined St. Jean Bay (adjacent to the famed Eden Rock hotel), which is rightly praised for its pulchritude; the swimming and sailing opportunities are excellent here.

If you don’t spy music and film stars in Gustavia or on St. Jean Bay, you might spot them on Nikki Beach, St. Barts’s most iconic beach club. Be that as it may, St. Barts is a place where anyone can live like a star.

Traveler Fast Facts


St. Martin/Sint Maarten, Anguilla, and St. Barts—part of the Leeward Islands of the Lesser Antilles chain—dot the northeastern Caribbean Sea. The islands are known for their sandy beaches; clear, swimmable turquoise waters; and refined cuisine. Some of the Caribbean’s most renowned hotels sit on the beachfronts of these three islands. 


The islands enjoy a tropical climate, with temperatures that average 80 degrees Fahrenheit and rarely drop below 68 or surpass 89. The dry, high season runs from December to April; the rainy season is from May to November, but barring any extreme storms, rains are typically scattered. Hurricanes and tropical depressions, if they occur at all, happen during the rainy season. 


All three islands accommodate private jets. Sint Maarten’s Princess Juliana International Airport is a busy Caribbean hub; other options include Anguilla’s Clayton J. Lloyd International Airport and St. Barts’s small Gustaf III Airport. Commercial flights to the islands are available on American Airlines, which dominates the Caribbean, and on Delta, JetBlue, and other carriers.


It’s best to take the Caribbean’s strong sun in increments, even during the cooler winter months when humidity is low and you might not feel the heat. Stay hydrated and pack light clothing no matter what the season. If you choose to go during the rainy months, watch weather reports for disturbances that may delay flights. Some hotels close during the low season—September and/or October—for freshening up. English is widely spoken, and taxis and car rentals are plentiful. 

Traveler Report Card


In St. Martin, La Samanna (A), which is part of the premier global Belmond chain, is the only game in town, luxury-wise. Its beach on Long Bay is top-notch and feels private, with few visitors from other resorts, and once you emerge from the sea, you have the choice of an infinity pool beside the alfresco restaurant (Laplaj, for lunch, which turns into La Spiaggia for dinner), or a lovely Mediterranean-style pool that hovers above the coast and just below Corail, the venue that offers tasty, bountiful breakfast.

With no town to speak of, Anguilla reflects a scene dominated by resorts—some of the finest in the Caribbean. Cap Juluca (A+), featuring whitewashed Moorish-style villas on the beach, is legendary for the warmth of its service and its position on perfect Maunday’s Bay. Aurora Anguilla (A), newly refashioned from the former CuisinArt, has retained the signature Cycladic look of its villas and boasts nine- and 18-hole Greg Norman–designed golf courses. The resort just announced private charters, with white-glove service, from airports in Fort Lauderdale, Florida, and Westchester, New York.

St. Barts’s Rosewood Le Guanahani (A+) represents the essence of privacy, located on its own peninsula between two beaches. There are two swimming pools, and the spa offers a “sense journey” that encompasses a hike followed by a body wrap, leg massage, and acupressure treatment. The Ocean Bay Pool Room boasts a private pool overlooking Marigot Bay.


Kontiki (A), on St. Martin’s Orient Bay, offers a French and Asian-fusion lunch menu that includes local Dover sole and mahi-mahi, lobster club sandwiches, tuna tartare, and quinoa poke bowls. You can also reserve beach loungers on its website. Also on St. Martin, Grand Case’s award-winning Le Pressoir (A) delivers fine Provencal cuisine; standouts include roasted lobster medallions with urchin cream and the house bouillabaisse. Anguilla’s Blanchards (A) is a beloved institution, serving red curry mussels and jerk chicken with sweet potato puree; the restaurant’s Beach Shack offers a popular happy hour with casual fare. For grilled steaks, octopus, and sea bass, Beach House St. Barts at the Rosewood Le Guanahani (A+) is the ticket. For dessert, save room for the “brookie”: a blend of a brownie and a cookie, served with vanilla ice cream.