Caribbean Queens: Timeless Luxury Resorts

These grand dame resorts consistently offer must-see, must-do and must-taste experiences in the most beautiful island settings.

The Caribbean is filled with every type of resort that caters to every type of traveler and every taste. But a regal few never fail to capture the attention of all. on nearly every island you’ll find that one timeless resort that continues to wow guests with its storied history or unique architecture, top-notch service or glamorous clientele — or all of the above. Whatever the magic formula, it works, drawing generations of visitors. But these classic resorts are not resting on their laurels. They constantly update their decor and expand their amenities, and a stay at one of these enduring gems makes for a majestic Caribbean honeymoon.

The Buccaneer, St. Croix

The Buccaneer, a pink-hued resort on St. Croix, the largest of the three U.S. Virgin Islands, opened in 1947 on the site of a 17th-century plantation and its old stone sugar mill is a great photo opp. Set on 340 manicured acres, the 138-room resort is a magical spot for lovebirds with not one, but three gently curving beaches. This is the place to try stand-up paddleboarding or indulge in his-and-her massages. After a few rounds on the golf course, dine alfresco at the Terrace Restaurant for a well-deserved feast. Room rates start at $397 a night.

old buccaneer st croix
Photo Credit: Lindsay Zammerkelt

Hotel El Convento, San Juan

On a charming cobblestone street in the heart of Old San Juan, the Spanish colonial Hotel El Convento is a 17th-century Carmelite convent turned luxury boutique hotel. Opened in 1962, its 58 rooms feature wood-beamed ceilings, terracotta-tiled floors, wrought-iron chandeliers and Andalusian tiles. Join fellow guests for a complimentary glass of wine on the rooftop terrace, then head to El Picoteo, the hotel’s fab tapas restaurant, to share spicy chorizo, patatas bravas and a pitcher of chilled sangria. Room rates start at $195 a night.

el convento san juan
Photo courtesy of Hotel El Convento

Round Hill Hotel and Villas, Jamaica

This posh hideaway on a former sugarcane and pineapple plantation near Montego Bay is an intimate and discreet escape, complete with a very private beach. Round Hill Hotel and Villas, with its 36 Ralph Lauren-designed rooms, 27 luxury villas and serene spa, has long attracted a who’s who list of privacy-seeking celebrities from Grace Kelly to Paul McCartney. Enjoy grilled lobster at the resort’s romantic waterfront restaurant and the jerk chicken at nearby Scotchie’s, a rustic roadside eatery — both are musts. Room rates start at $479 a night.

jamaica round hill hotel
Photo courtesy of Round Hill Hotel and Villas

Caneel Bay, St. John

Opened in 1965 by Laurance Rockefeller, you’ll be seduced by the understated luxury of Caneel Bay. The 166-room retreat is set in the Virgin Islands National Park on one of the Caribbean’s most eco-friendly islands. Hike along lush rainforest trails or snorkel pristine beaches like Trunk Bay, or never leave the resort and its blissfully phone- and TV-free rooms. Wriggle your toes on one or all of the seven sugar-soft strands (including Honeymoon Beach) and savor delicious West Indian fare in the candlelit restaurants. Room rates start at $489 a night.

caneel bay st john
Photo courtesy of Caneel Bay Resort

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