These Caribbean Islands Make For The Perfect Winter Escapes

Beat the winter blues.

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best caribbean islands for winter

Nothing stomps out the winter blues faster than trading big, heavy coats for skimpy bikinis. When the thermometer starts to dip, it’s prime time to plan a warm-weather trip to the Caribbean for days filled with swimming, catching rays, and sipping rum punch. While the region provides plenty of incredible destinations, not all are so easy to reach. Some places require hopping on connecting flights, an air shuttle, or a ferry. There’s no denying that St. Barts and Anguilla warrant the additional transport hurdle. With that said, if you’re short on time or just don’t want to deal with the hassle, other islands cut out the extra time in the sky and make travel days much shorter — thanks to direct flights from major East Coast hubs, including Atlanta, Boston, Miami, and New York. That means fewer hours waiting for vacation to start and actually getting to enjoy each and every second of PTO.

From Aruba to Turks & Caicos, these sun-drenched Caribbean islands are the perfect easy winter escape.

Grand Cayman


American Airlines, Delta, JetBlue, and Southwest all operate non-stop flights to Grand Cayman. The largest and most accessible of the Cayman Islands makes trading the cold for warm weather and sunshine a breeze. Spanning 76 square miles, it’s packed with an abundance of attractions. Impossibly photogenic Seven Mile Beach steals the show. Other can’t-miss experiences include swimming with stingrays at Stingray City and seeing rare blue iguanas at Queen Elizabeth II Botanic Park.

Where to stay: The coolest spot to hang up your sun hat and sarong in Grand Cayman (and quite possibly the Caribbean), Palm Heights attracts a stylish crowd who flock to this glamorous slice of paradise on Seven Mile Beach to laze under yellow beach umbrellas, prioritize well-being at the spa, and snooze in ocean-view suites.

The Bahamas

The Bahamas ranks among the top holiday hotspots for U.S. travelers. Certainly the fact that Nassau sits just 185 miles from Miami, is serviced by direct flights on numerous airlines, and enjoys year-round warm weather bolsters the appeal for visitors. Far more than just a popular cruise stop and springboard for exploring the rest of the archipelago, the capital supplies stunning beaches and off-shore coral reefs, plus it’s a short drive to resort wonderland Paradise Island.

Where to stay: Part of the sprawling Baha Mar complex, the luxurious Rosewood Baha Mar sits right on Cable Beach. Guests can pack days building sandcastles, swimming in the ocean, hitting the links at the Jack Nicklaus-designed golf course, and splashing around the waterpark or just chill by the pool and maybe book an afternoon spa session.

Dominican Republic


Unlike some of the smaller Caribbean nations, the Dominican Republic actually has a few airports that welcome international direct flights, which gives U.S.-based travelers ample options. Check into an all-inclusive in Punta Cana and spend the week flashing your yellow wristband for food, drinks, and watersports or head to the capital city of Santo Domingo to explore historic landmarks and more local beaches.

Where to stay: Located less than 20 minutes from Punta Cana International Airport (PUJ), Eden Roc Cap Cana, the only Relais & Châteaux property on the island, oozes luxury in a laid-back, leisure-ready way and possesses a spate of five-star perks — notably a private beach club, an award-winning spa, delicious food, and elegant villas.

Turks and Caicos

Turks and Caicos is arguably best known for Grace Bay — a pristine stretch of white sand and translucent turquoise water that continually tops lists of the most beautiful beaches in the world. Besides its postcard-perfect claim to fame, the gateway island of Providenciales also boasts many oceanfront resorts and lively restaurants as well as superb snorkeling and diving along the 14-mile barrier reef.

Where to stay: Keen to stay somewhere intimate and serene? Point Grace, a boutique retreat and member of Small Luxury Hotels of the World right on the shores of Grace Bay, gives off tranquil vacation vibes. Highlights include an ocean-view spa for marine algae wraps and aloe facials, al-fresco dining, a sparkling pool, and charming cottages.

St. Martin


Friendly and endlessly captivating with personality in spades, St. Martin is a really interesting Caribbean destination in that it’s split into two separate countries: the northern French side, called Saint-Martin, and the southern Dutch part, known as Sint Maarten. So it’s basically a two-for-the-price-of-one-direct-plane-ticket type of situation. Regardless of where you decide to hunker down, sandy beaches, lively nightlife, cocktails made with guavaberry liqueur, and duty-free shopping await.

Where to stay: Upon landing at Princess Juliana International Airport (SXM), travelers are only about 15 minutes from La Samanna, A Belmond Hotel. The longtime crown jewel of St. Martin luxury continues to wow guests with its grand sea-view lobby, spa, and the largest private wine cellar in the Caribbean, plus new pool villas.


Barbados is perhaps best known as the birthplace of Rihanna. Of course, that’s just one of the many cool things about the island country in the Lesser Antilles of the West Indies. West African and British influence permeate local culture, as evidenced by the cuisine and traditions like afternoon tea. There are many idyllic beaches and botanical gardens. Cruise ships dock in the colorful capital of Bridgetown, which also happens to be an ideal place to taste your way through the thriving culinary scene. Be sure to try Cou Cou and Flying Fish, the national dish.

Where to stay: Sandy Lane, part of the Leading Hotels of the World portfolio, draws a steady stream of five-star aficionados. With a spectacular setting on a crescent of white sand and perks like an exclusive spa, tennis courts, and championship golf, it’s not hard to see why it’s such a hit with discerning travelers.

Saint Lucia


Because Saint Lucia exudes this unspoiled, off-the-beaten-path charm, some travelers might be surprised to learn that it’s linked to the United States by a number of non-stop flights. Defined by the dramatic beauty of its UNESCO-listed Pitons, the Eastern Caribbean island nation also offers volcanic beaches, coral reefs, hot springs, waterfalls, and lush rainforest. While it’s definitely a place that’s prime for unwinding, thrillseekers will have a blast scuba diving, snorkeling, kitesurfing, hiking, and zip lining.

Where to stay: Perfect for honeymoons and couples getaways, Jade Mountain is a design-forward, adults-only cliffside hideaway that’s designed to inspire romance. Guest sanctuaries are constructed without a fourth wall to take advantage of the soul-stirring panoramas and flaunt prismatic tiled infinity pools.

St. Thomas

The largest and easiest to reach of the U.S. Virgin Islands, St. Thomas is home to an international airport and a busy cruise ship port. Once you arrive at this popular vacation spot, it’s all sunbathing on the sand, snorkeling with marine life, and frolicking in the crystalline tides. Want to do more than just hang on the beach? It’s quite a cosmopolitan destination with Danish architecture, duty-free shopping, and cultural attractions like the 1680-built Fort Christian in the capital of Charlotte Amalie.

Where to stay: A welcome addition to the island’s clutch of accommodations, The Pink Palm Hotel, a boutique adults-only getaway, has quickly become a hit among aesthetically oriented vacationers with a penchant for the finer things. It’s an oh-so Instagrammable oasis with scenic harbor views, retro-chic tropical decor, and an emerald-tiled infinity pool.



Aruba is one of those places that people return to year after year. Devotees tout the gorgeous weather, equally blissful beaches, and rich local culture as some of the most appealing aspects of a vacation to the 70-square-mile Dutch island. Looking for nightlife? Unlike some sleepier Caribbean destinations, Aruba has casinos, lively bars, and dance clubs. And the ease of travel, translates to a stress-free, fun-filled trip that’s a cinch to plan.

Where to stay: The ultimate getaway for relaxation seekers, Bucuti & Tara Beach Resort is a serene, adults-only oasis on a pretty stretch of shoreline. A departure from the many large-scale properties on the island, it feels small and boutique with thoughtful amenities like seaside yoga, oceanfront movies, and a breezy beach bar.

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