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02/21/2024: The Pilots of the Caribbean

A true island-hoping insider explains the ins and outs of the the best the region has to offer; and we round up the best new hotels with water views from around the globe.

February 22, 2024 By MAURA EGAN
The Rosewood Little Dix Bay. Photo: Courtesy Rosewood

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From left: Tradewind Aviation aircraft. Photo: Christian Oth; The Rosewood Little Dix Bay. Photo: Courtesy Rosewood

The Pilots of the Caribbean

Tradewind Aviation, founded by brothers David and Eric Zipkin in 2001 to combat the inconvenience, stress, and long lines at the airport, is an aviation company that offers private charters as well as scheduled flights around North America and the Caribbean. Each of their 29 planes is equipped with two pilots and excellent snacks for a smooth ride, which is not always the case on those island puddle jumpers.

I joined Zipkin on a recent flight from San Juan (where they have their own private lounge, as well as staffers who can expedite you through security and boarding) to Virgin Gorda where they have recently started service. Zipkin is a trained pilot (which was comforting when a rainstorm rapidly blew through our flight path) and an excellent resource for the more hidden spots in the Caribbean. “We like to fly to hard-to-reach destinations so our customers can really experience something different,” he says. While St. Barts is not off the beaten path, Zipkin spends a lot of time there and offers us his hidden spots. “It’s not all popping champagne corks and yachts.” —Maura Egan

Go for the Nature
“You need a car in St. Barts because there are not that many taxis, and they usually get rented out like a fleet by the super wealthy when they come to town. Hike along the Colombier Beach trail, which takes about 25 minutes each way. The upper trail is more difficult because it’s steep. The beach is one of the most secluded beaches on the island. I do it about four times a week when I am there. The Anse de Toiny is a wild coastline and has some great hikes as well. Saline Beach is untouched. It’s about a 10-minute walk from the parking lot. You go over the bluffs to get to the beach and it’s totally pristine. There are no hotels or restaurants here.”

Get in the Water
“The island might be known for its yacht scene, but it’s a great place for actual water sports. The Grand Cul de Sac Beach is a shallow lagoon, so you can paddleboard or kayak. I do a lot of kiteboarding here. You can also scuba dive in St Barts. It’s not the Great Barrier Reef, but it’s good. There’s also lots of sea turtles. You can also just rent a catamaran and sail around.”

Eat at the Local Spots
Fish Corner in Gustavia serves excellent seafood. The owner is a local fisherman. There’s not a view, and it’s not a party spot, but the food—like the ceviche and the tuna tacos—is delicious. Eddy’s right in town is a really beautiful spot and serves Creole and Caribbean food (goat curry, papaya salad), as well as some French stalwarts (beef tenderloin). There’s a new place called the Beefbar, which is an outpost of the international restaurant group that recently opened at the Hôtel Barrière Le Carl Gustaf. The views are excellent, so go for a sunset cocktail.”

Avoid the High Season
“After Easter, it clears out and it’s a nice time to come. There are less crowds and everything is still open. July and August are a great time to come . . . fewer folks and a great vibe. September and October are hurricane season so I’d say the other great times are early November and early December before the mad rush for Christmas and New Years.”

Zipkin’s Picks Beyond St. Barts

Anguilla: “It’s really relaxed and slow going. The beaches are incredible and it’s a flat island with this pink sand, which sounds like a cliché. The food is surprisingly good. It’s not just the usual conch fritters. I recently had an amazing meal at Belmond Cap Juluca.”

Barbuda: “There’s very little development here because it was destroyed during Hurricane Irma. The Discovery Land Company—the people behind ultra luxe private clubs like Baker’s Bay in the Bahamas and the Yellowstone Club in Wyoming—recently opened a resort here in 2020.”

St. Eustatius: “This Dutch island, otherwise known as Statia by locals, was really probably best known for having an oil transfer site. Now there’s the new Golden Rock Resort, a 32-room eco-friendly property which opened up in 2021. It’s the island’s first luxury hotel.”

Virgin Gorda: “The sailing is great in the BVI. It’s not as rough as other parts of the region, so amateur sailors can do it without a captain. You can rent a 40-foot-long catamaran which can sleep up to six people and cruise around. The Rosewood Little Dix Bay, which used to be the old Rockefeller estate, is great.”

Necker Island: “Richard Branson’s private island has become the natural breeding ground for some of the world’s most endangered species including Madagascar lemurs and giant tortoises. The resort is also very committed to sustainability, powering most of the island with wind and solar energy. The resort had previously only been available to guests who could reserve the entire island, but now during certain times of the year people can book individual stays.”

From left: Boca de Agua. Photo: Courtesy Boca de Agua; Romazzino, A Belmond Hotel. Photo: Courtesy Belmond

Six Senses La Sagesse​​
Set on 38 acres in the southern part of Grenada, this low slung property (no building will be higher than a palm tree) opening in April will follow the brand’s sustainable ethos. Ingredients for the restaurant and spa will come from the on-site gardens, the seafood will be sourced from the local fisherman, and the property will be plastic-free. The spa will be one of the best in the Caribbean with a holistic anti-aging center.

Pensione America
Once a private villa (and before that a hospital for American soldiers during WW1) Pensione America will be an elegant spot in Forte dei Marmi, which is often called the Hamptons of Italy. The owners behind intimate properties like the new Hotel Violino d’Oro in Venice and the Grand Hotel Minerva in Florence will transform this into a chic retreat for adults only.

Our Habitas Santa Teresa
The cool kids of the Our Habitas hotel group, who made their name originally in Latin America, are putting down roots in Costa Rica this spring. Located on the southernmost tip of Nicoya Peninsula in the surf town of Santa Teresa, the hotel will feature 45 earth-inspired rooms and 10 luxury tents. Expect communal style experiences like sunset bonfires, horseback rides on the beach, meditation classes, and waterfall excursions.

Boca de Agua
Located in up-and-coming Bacalar, Mexico (the Habitas folks have a place here as well), this property which will open later this year was designed by Mexico City–based architect Frida Escobedo. The resort is made up of 22 treehouse style villas, two restaurants, a petanque court and a spa set among mangroves.

Romazzino, A Belmond Hotel
The brainchild of Aga Khan back in the 1960s, this resort, located on Sardinia’s famed Costa Smeralda, is being revamped by the Belmond group. This whitewashed resort will feature 100 retro-style rooms, suites and villas, all with private pools.

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