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The Best Caribbean Destinations for This Holiday Season

The holidays are fast approaching, meaning it’s time to start thinking about your next Caribbean vacation (that is, if you haven’t already planned a Caribbean trip in the meantime).

For us, there’s nothing better than Thanksgiving, Christmas or New Year’s in the Caribbean. As those in wintry places dream of a White Christmas, why not dream of a White Sand Christmas?

Some destinations are tailor made for the holidays, thanks to that perfect combination of beaches, restaurants, nightlife and, most importantly, hotels, with an emphasis on accommodating multi-generational trips — because this time of year, it’s about spending time with family.

Here are the best holiday destinations in the Caribbean right now.

Aruba It’s as good of a family destination as there is in the Caribbean, thanks to spacious hotels, ease of getting around and a multitude of activities for travelers big and small. Whether you’re looking for a luxury getaway at the Ritz-Carlton or bringing a large group to the Aruba Marriott, there are a host of places on the island for the perfect holiday getaway. Looking for a romantic holiday season? Try the adults-only Bucuti Tara.

high above round hill.

Jamaica Spending the holidays at a classic Jamaican resort like Half Moon or Round Hill is just about the quintessential Caribbean holiday experience, as these resorts were among the pioneers of winter travel to the Caribbean more than a half century ago. But if you’re bringing your loved ones to Jamaica for the holidays, there are so many great options, from the new Jewel Grande all-inclusive to Beaches Negril.

afternoon tea curtain bluff

Antigua Another one of the Caribbean’s greatest family destinations, Antigua has carved out a niche with a beautiful collection of family-friendly resorts, from the venerable Curtain Bluff to more boutique options like the South Point hotel.

Barbados

Barbados It’s hard to think of a more “grand” destination for the holiday season than Barbados, a place where everything seems to have a bit of panache. And that’s particularly true at the island’s legendary hotels, from the Platinum Coast’s Colony Club and Tamarind to the Ocean Two on the island’s south coast.

The Cayman Islands One of the Caribbean’s most livable places, the Cayman Islands makes for a terrific holiday getaway, with a diverse hotel product emphasizing larger, condo-style rooms and one of the Caribbean’s hottest dining scenes. And there’s something for everyone, from the world-class Ritz-Carlton Grand Cayman to out-of-the-way spots like the Southern Cross Club or Little Cayman Beach Resort (above) on Little Cayman.

Greenwood Beach on Cat Island.

Cat Island Still one of the Caribbean’s best-kept secrets, the island of Cat Island in The Bahamas has long been an under-the-radar family destination, particularly its popular Fernandez Bay Village resort, a haven for multi-generational trips. It’s one of several great places to stay on the beach-filled island, from the more eclectic Greenwood Beach Resort to the boutique Shannas Cove.

Grenada The Spice Isle is increasingly finding itself on the radar of well-informed travelers, and that’s thanks to a genteel, warm feel and a lovely collection of authentic Caribbean resorts. Whether you choose the world-class Calabash or the beautiful little True Blue Bay, a Grenadian holiday is a unique experience. In many ways, Grenada is the Caribbean as it used to be — and that’s a wonderful thing.

Martinique The star of the French Caribbean, this is a diverse, rich island that will produce a sophisticated holiday getaway. Instead of jetting off to Europe for Christmas or New Year’s, why not take a short trip to Paris in the Caribbean? Try some of the island’s lovely boutique resorts like French Coco and Cap Est.

Dominican Republic There’s a reason the Dominican Republic is the most popular destination in the Caribbean by volume — and it’s in large part due to the overwhelming variety of resorts to choose from, whether all inclusives like Zoetry and Barcelo or ultra-complete resorts like Casa de Campo. Looking for a more intimate stay? Try Puerto Plata’s Casa Colonial.

Curaçao The Dutch Caribbean’s cosmopolitan center makes for a very different kind of vacation — active, energetic and focused on culture. Thanks to its marvelous historic city of Willemstad, the island offers the kind of getaway that’s very hard to find in the Caribbean region. The best way to see it? Right in the heart of downtown at properties like the Kura Hulanda and the Renaissance.

St Kitts The island’s new crown jewel, the Park Hyatt St Kitts, is already taking bookings, and there might be no better destination for a luxury holiday season in the Caribbean right now. But tiny St Kitts is full of options, from the great-value St Kitts Marriott to smaller resorts like the Ocean Terrace Inn.

The Sands

Providenciales — Provo has rebounded quickly from the hurricanes of last month, and most of its resorts are already either back up and running or ready for the winter season, from The Sands at Grace Bay to the Shore Club. Because Grace Bay Beach is just about as good as it gets.

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