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Best Places to Escape Winter in the Caribbean

Long before the arctic-blast blew its way into many areas of the country, I was dreaming about a tropical vacation. Somewhere warm with good food, white sand and sparkling blue water.   Nothing fancy, just a chance to escape the grey skies, bitter cold and blustery winds at home.

So with the warmth of the Caribbean calling my name, here are my top picks.

Cayman Islands

You know I’m not one to just sit on the beach, but doesn’t this cabana look wonderful right now?  The Cayman Islands are a favorite of adventure seekers, beach goers and wildlife enthusiasts.  You spend the day on Seven Mile Beach, visit the Cayman Turtle Farm or hike the interior of Grand Cayman on the Mastic Trail (2 miles).  And then there’s the scuba diving and snorkeling in a true underwater paradise.

Travel Guide


St. Kitts & Nevis

If you’ve never been to the sister islands of St. Kitts & Nevis, make sure you put a visit on your list.  The resorts here are impressive and the scenery lush and gorgeous.  While the main attraction is the beach, you’ll find some excellent adventures and history around the islands.  Visit the British colonial town of Basseterre, the Brimstone Hill Fortress and Berkeley Memorial Clock for some of the most photographed sites.  St. Kitts is a bit wilder and louder than the quieter sister of Nevis.  And you never know when you might spot a celebrity frolicking in the surf.

Lonely Planet Caribbean Guide



With strong British roots, having gained independence in 1966, the island continues to hold afternoon tea and horse races at Garrison Savannah.  When you’re tired of laying on the beach sipping your rum cocktail, take off for the Soup Bowl to watch the surfers (or do some yourself), hike the amazing shoreline of Bottom Bay (go in the morning), and visit Animal Flower Cave to swim in its rock pools and take a few hundred photos.

Fodor’s In Focus Barbados


U.S. Virgin Islands

The three islands that make up America’s Caribbean paradise have a lot to offer.  You could spend all your time on one island, but for a little more fun, plan a day or two on all three.  You’ll get a healthy dose of beaches, pampering, wildlife and colonial history.   If you are into hiking, you can explore 22 different trails within the Virgin Islands National Park (St. John) which contains Annaberg Plantation, Caneel Bay, Cinnamon Bay and Trunk Bay.  Take your camera and beach gear and spend the day at Magens Bay (St. Thomas), well-known for its photogenic coast and amazing swimming conditions.

Frommer’s Virgin Islands


Turks & Caicos

Known for its crispy conch fritters, relaxed vibe, snow-colored sand and shimmering surf, this network of 40 islands is a perfect, secluded getaway for beach lovers and snorkelers.  Make sure you spend a day at Grace Bay (Provo) which is popular for its 12 miles of beach, snorkeling at Bight Reef and some of the area’s best-liked restaurants.  For the snorkeler looking for another amazing spot to explore the underwater world of sea creatures, head over to Smith’s Reef (Provo).

Fodor’s In Focus Turks & Caicos Islands


Where is your favorite place in the Caribbean?

More from Samantha Brown:

3 Great Beaches for Treasure Hunting

Honeymoon Destinations

Best City Beaches

Best Beaches for Adventure

This Post Has 11 Comments

  1. Sam, If one was to stay in Turks and Caicos and want to snorkel and have night life and good restaurants and it all, which part of the island would you stay at?

  2. Hi Samantha! As a travel consultant out of the Boston area, I agree with your destination choices! I LOVE those places. I think Barbados is an excellent option for winter vacations and so thank you for including this lovely island in your roundup. Barbados offers the finest beaches, accommodations, restaurants and golf courses! What’s more, Bajans are quite friendly and love to share their island with visitors. In addition, I would like to suggest Aruba. The temperature is a perfect 82 degrees pretty much throughout the year. Aruba is an island gem with lots to offer, too. From beaches to restaurants to fun island tours and casinos – the island boasts a very high repeat visitor ratio. Now, both islands (different from each other in terms of topography) are away from the path of hurricanes – so good choices for Fall trips. Good job on your site and updates! Thank you so much.

  3. I thought Caneel Bay is closed until 2020 along with their sister resort Little Dix in Virgin Gorda? I love Caneel Bay but thought they were having a very difficult time rebuilding.

  4. For me it has always been Maho Bay and the wonderful memories that I have from that location. My parents and I visited St. John twice and enjoyed each time immensely! They are now gone and I have only dusty video tapes of those days. It was quite a journey from a small wintry town in New Hampshire to the beautiful, warm Caribbean aboard the grand ship QEII.

    That one trip made us all want to return to the islands and we did. A total of three times, including a stay at Cinnamon Bay campground which had glorious beaches and fantastic warm water! We did not spend all of our time sunbathing and in the water. We took tours on many islands and there was so much to see hear, eat, and drink!

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