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The Caribbean's Finest

Our panel of travel experts pick their favorite destinations across the region, and the best hotels, restaurants and golf courses on each island
Larry Olmsted
From the Print Edition:
Ernie Els, November/December 2012

Spanning hundreds of islands, thousands of miles of gorgeous turquoise waters and dozens of unique cultures, the Caribbean is a perennial vacation favorite. It is also incredibly diverse: From posh tiny private island getaways to cosmopolitan urban resorts, secluded beaches to bustling casinos, world-class diving to world-class golf, there is truly something for everyone. This variety is coupled with excellence—almost every island has 5-star potential, with sumptuous accommodations, first-rate spas, and gourmet cuisine.

This makes the biggest problem in planning a Caribbean vacation deciding where to go—and the problem keeps getting more complicated as excellent new properties open. While we cannot stop progress, we can do the homework for you. By polling our experts, we have narrowed down the very best the Caribbean has to offer (we also threw in the popular Bahamas). As always in our uniquely critical travel surveys, we take a different tact than most magazine polls: we do not rely on unknown voters who may or may not have actually been where they say, or employees of the properties, and we do not cater to advertisers. Instead, we have assembled a panel of renowned travel experts, including some of the world’s best travel agents, the ones that celebrities and top executives use to plan their vacations, plus journalists, specialists and industry veterans, all of whom vote only on the places they know.

Because the Caribbean is composed of so many islands, cultures and economies, it is dynamic and always changing, and our poll reflects this. Perhaps the biggest story our experts told was the resurgence of Puerto Rico—on every front. Newer luxury resorts like the St. Regis Bahia Beach and W Retreat Vieques have proven immensely popular, while venerable properties have kept pace. Everyone in the travel business is eagerly anticipating the Ritz-Carlton Reserve at Dorado Beach (opening 12/12/12), which was called the next big thing, not just in the Caribbean but in the world, by several of our panelists.

Puerto Rico is also booming on the golf front, with Bahia Beach and Trump International joining the highest tier of Caribbean courses, while the island’s grand dame, Dorado Beach East, was just revamped and is better than ever. The brand new Links at Royal Isabela, so new almost no one has been there yet, may end up stealing the show. “This rediscovered island is getting the attention it deserves with multiple new and exciting properties and investment in the area. San Juan is becoming a Caribbean hotspot again, and Puerto Rico is a great destination with the rain forest for eco-tours, kayaking on bioluminescent bays, and so much more for the adventure seeker. I am packing my bags already!” says Anne Scully, industry legend and President of McCabe World Travel, annually ranked as one of the nation’s top 10 travel agents.

One thing that quickly becomes evident is how strong the Caribbean is with small luxury resorts and hotels. On some islands there is no line between “large and small,” and since the Caribbean has relatively few luxury properties that would be considered large in other vacation destinations, the focus here is on intimate. Nowhere was this as evident as on tiny St. Barths, where virtually every top hotel—and there are lot of them—was named in both size categories by panelists, forcing us to abandon size as a criteria for that island altogether. After all, even the “biggest” hotel on St. Barths would be a boutique anywhere else. We saw similar confusion on Anguilla, where Cap Juluca and CuisinArt, with 95 and 93 rooms respectively, both got votes for best large—and best small—hotel.

There were a few things our panelists agreed on, and when it came to unanimity, the Four Seasons Nevis could not be beat: it got the most votes of any property and every vote cast for the Federation of St. Kitts & Nevis (and yes, there are other hotels). It also swept all the votes for best golf (yes, there is another high-profile golf course). Rosewood’s Little Dix Bay, British Virgin Islands, also won “best large resort” unanimously. On Grand Cayman, the hidden gem Cotton Tree proved not so hidden in sweeping every vote in the boutique category, and Ritz-Carlton’s Blue took every vote as best restaurant. While not quite unanimous, other landslide winners that bowled over all comers included Sandy Lane on Barbados, Casa de Campo in the Dominican Republic and La Samanna on St. Martin. On other islands and in other categories, the results were much closer and harder fought, and our panelists even locked up for a couple of ties, which just shows how prolific the Caribbean is when it comes to hospitality.

Our biggest surprise came through an act of omission. Because there are so many possible destinations, we limited the poll to the most popular and developed islands, and some less-visited ones had to be left out, including Dominica, Saba and Grenada. One place left off our list was the largely undeveloped Turks & Caicos Islands. Though not technically part of the Caribbean, our panelists did not care and did not hesitate to exercise their write-in option. As Michael Holtz, a top-tier luxury travel agent and founder of SmartFlyer exclaimed, “You left out Turks! It really is a MUST with Parrot Cay & Amanyara there.” Amazingly, the archipelago made a strong showing in several categories—as a write-in. The sands of Grace Bay tied for first in the best beach category for the entire Caribbean and yoga-centric Parrott Cay, a famed celebrity haunt, showed up in best resort and best spa categories.

Our panel proved to be as opinionated as ever when it came to Caribbean travel, and this is what they loved.

Best Large Resort or Hotel, Caribbean

TIE: St. Regis, Bahia Beach, Puerto Rico
Casa de Campo, Dominican Republic
Sandy Lane, Barbados

This category was hotly fought, but these three winners have one thing in common: they are all “complete” resorts, with golf courses, lavish spas, multiple restaurants, other amenities and a wide range of lodging choices including villas. “Casa de Campo remains the Caribbean’s most complete and satisfying retreat…indulge in an incredible array of activities ranging from tennis—with ball boys—to shooting, horseback riding and even polo,” says Golf Odyssey publisher David Baum. Super-agent Scully is one of many fans of the St. Regis, “The resort is exquisite with two miles of private beach and 18-holes designed by Robert Trent Jones. Pamper yourself at the Remède Spa, dine at Fern, a signature restaurant of Jean-Georges Vongerichten.” As for Sandy Lane, “Since 1961 this Palladian-style beach resort has been setting standards in the Caribbean for elegance and grace. How does it stay fresh?  With three premium golf courses, a 7,000-square-foot pool, state-of-the-art spa and tennis facilities and museum-grade art. It’s simply Barbados’ most luxurious resort,” notes USA Today travel editor Veronica Stoddart.


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