5 Expensive Caribbean-Style Resorts To Stay At During The Winter Season

For a good portion of the U.S. — the world, in fact — it is about to get cold, really cold, and many a thought turns to sunny, warmer climates.

Clear blue waters, white sands and tropical anything are beckoning. And for those who want the best of everything, below are five suggestions — in no particular order — to ponder and potentially book.

Note prices are for the first half of 2022 and do not include taxes, gratuities or any extra services. Prices may also differ based on availability

1. Mystery Resort: Ever Hear Of Pine Cay?

If you haven’t, that’s part of its charm. Unlike St. Barth’s, the Caribbean playground of yachts this time of year and all about the flash, Pine Cay is meant to be its polar opposite. Which is probably why you haven’t heard of it.

Not to be confused with Pine Key in the Florida keys, this 800-acre private island is part of Turk and Caicos and was judiciously developed in the 1970s with an eye on quiet luxury.

It’s a short, 90-minute flight from Miami and there is only one hotel, boasting 10 beachfront rooms or two freestanding beachfront suites. There are private home rentals, as well. And of course, two miles of white sand.

Rates? A premium beachfront room starts at $1,650 at night. Not too expensive, but what price for beauty, peace and quiet?

2. So You Want the Flash, Sort Of: Hotel Le Toiny, St. Barth’s

Yes, there really is yacht gridlock right now in Gustavia, the capital of the island of Saint Barthélemy, better known as St. Barth’s.

There is no lack of luxurious resorts or homes to stay, but Hotel Le Toiny stands out as being part of the fray — St. Barth’s is a small island —  yet still apart: the resort has 22 separate villas, each with a private pool and terrace overlooking Toiny Bay. The Beach Club is a favorite spot to dine on the beach, and the quiet allows a good book to be read anywhere in the resort.

At $2,706 a night with one bedroom, the Signature Suite’s pool offers a perfect view of the setting sun, no doubt with a cocktail in hand, or try the La Villa Nureyev, which has four bedrooms and has its own private massage area — at $12,248 a night.

Stay here to luxuriate or hop in a car and head to Gustavia for shopping and nightlife.

3. Find Your Own Shaman: Rosewood Mayakoba, Playa del Carmen

Who better to know top places to go in Mexico than the readers of Travel + Leisure, who voted this resort as one of the “World’s Best” in 2021.

Located in the heart of Mexico’s Mayan Riviera, Mayakoba consists of four resorts, more than 25 restaurants, a dive and sports center, nature trails, a PGA championship golf course, tennis courts and shopping.

But what made this place stand out to T + L readers was one of the experiences: Working with a Shaman “to determine personal patterns and your goals for self-love,” creating a program to help you on a journey of self-discovery, “utilizing the elements of nature and ancient pre-Hispanic teachings as mentors.”

After a tough two years, who doesn’t need that?

The Presidential Suite, which opens up to the beach, starts at $14,715 a night.

4. The Shopping Set: The Colony Hotel, Palm Beach, Florida

Winter is high season in Palm Beach and the people — and yacht watching — are spectacular. What better perch than at the refreshed Colony Hotel? Its distinctive pink-hued exterior sets it out from the crowd and is steps away from shopping on Worth Avenue and assorted beach activities.

What has grown over the years is the avenue’s art scene, with more galleries than ever.

Book the luxurious Villa Jasmine by AERIN (that’s Aerin Lauder of Estée Lauder fame) with a price to be determined, as you have to contact the hotel to find out. A standard double room starts at $1,060.

And the hotel allows pets! (For a small fee.)

5. Welcome to the Jungle: Amanera, Dominican Republic

While Casa de Campo gets the most publicity, this resort receives the kudos. Amanera is perched in the jungle overlooking the golden sands and ocean on the Dominican Republic’s north coast.

Twenty-five freestanding villas (casitas) have beach views and 13 have private pools. The Aman Golf Course is nearby. But what excites visitors is the number of activities, including ocean kayaking to exploring the jungle, some to find botanical remedies.

A bay view pool casita starts at $3,200 per night. And if you really got to get there fast, the resort offers VIP fast-track and helicopters for airport transfers.

Photo: Top photo: Parrot Cay; all other resort photos courtesy of the resorts