These Private Caribbean Hideaways Are Perfect for a Winter Escape

Editor’s Note: Travel might be complicated right now, but use our inspirational trip ideas to plan ahead for your next bucket list adventure.

Winter often calls for a beachy week or two away. But this season, the desire for personal space ranks even higher than the need for a dose of sun. “We’re seeing a trend of extended families or groups of friends who’ve spent months separated seeking a safe way to come together in a remote destination where they can feel free,” says Brooke Lavery, a New York–based travel expert at Local Foreigner. “They’ll fly privately to create a bubble, seeking out a total change of scenery from home.”

Larger Caribbean properties are capping occupancy at between 30 and 60 percent, and tours and attractions are also reducing capacity. That means small hotels and private-island resorts — where social distancing happens naturally — are proving to be the perfect fit.

“This year it’s about quality time in your own space, apart from the crowds,” agrees Susan Moynihan, of the Honeymoonist/Largay Travel in Waterbury, Connecticut. “My clients are looking at private villas or at stand-alone residences that are part of bigger resorts. Having your own swimming pool is key, so you don’t mix with other guests.”

In the Turks and Caicos, a new oceanfront villa at Sailrock Resort (villa from $2,265) fills the bill: it’s a self-contained three-bedroom unit with its own pool, two miles from the island’s other 35 suites and villas. Or opt for Ambergris Cay (doubles from $1,200), a 10-suite, six-villa private-island resort, which has its own airstrip. Last winter, Cheval Blanc St.-Barth Isle de France (villa from $15,960) added the five-bedroom Villa de France, with two infinity pools and views of Flamands Beach.

And at Bequia Beach Hotel (doubles from $300), a 58-room retreat on a seven-square-mile island in St. Vincent and the Grenadines, two spacious, stand-alone villas were unveiled in November. (The smaller of the two sleeps eight; both are available for a minimum of five nights.) The resort has also added a private nine-seater Beechcraft King Air B200 plane, so guests can avoid the connecting commercial flight to the island from Barbados.

Nearby Petit St. Vincent (doubles from $1,350) has just 22 cottages and villas on its 115-acre, palm-fringed private island. Already far removed from the U.S. — getting there typically requires at least two flights and a 30-minute boat ride — the resort is upping the ante this year. Guests can now book up to four neighboring cottages, with each “pod” getting its own beach and dining area.

If you have the means, renting an entire island is also an option. Saba Rock (buyout from $5,175), which has been closed since Hurricane Irma hit the British Virgin Islands in 2017, is slated to reopen in the first quarter of 2021. Set on a one-acre cay in the North Sound, it has seven rooms, two suites, and a dive shop for outfitting private charters around Virgin Gorda.

A version of this story first appeared in the December 2020 issue of Travel + Leisure under the headline Your Own Personal Paradise.