20 Islands Perfect for a Winter Vacation

Island Getaways This Winter

1/21
Many people are tied to family expectations and obligations this time of year, but have you considered giving your family the ultimate Christmas present-an island vacation? Get away from the hustle and bustle and relax at one of these island retreats this season.

US Virgin Islands

2/21
Pick any of the U.S. Virgin Islands, and you'll be rewarded with warm weather, island breezes and crystal-clear water. Feel like you don't have enough time in your schedule? Opt for a long weekend. The best part-you don't even have to worry about hunting down your passport.

The Bahamas

3/21
The Bahamas are open for tourists after the horrible hurricanes that ran through the islands earlier this year. And the best thing that people can do now, is just visit. Cruise lines are expanding their ties to the islands with new private islands for Disney Cruise Lines and Royal Caribbean already in the works. The Bahamas are made up of 700 islands, with great options for every traveler.

Koh Lanta, Thailand

4/21
Wanting to experience someplace a little more exotic, half a world away? Koh Lanta is considered to have one of Thailand's best-hidden beaches. This is for the more adventurous traveler, but you'll be rewarded by getting to see authentic Thailand without the swarms of tourists.

Iceland

5/21
You don't have to go on a tropical island retreat to still have an island getaway, and winter is the perfect time of year to visit some of the colder islands like Iceland. Not only are you more likely to get to see the Northern Lights, but you'll also avoid the crowds of the tourist high season (mid-June through August). Just be sure to dress warmly or spend some time at the Blue Lagoon hot springs as temperatures in December are normally in the 30s.

Dominican Republic

6/21
Club Med just opened its newest location, Club Med Miches Playa Esmeralda, and it is the ultimate in all-inclusive relaxation. From a next-level culinary experience to just enjoying the unspoiled beauty of Miches, you won't have a worry in the world while staying here. Feeling a little unsure about traveling to the Dominican Republic right now? Get the lowdown on island safety from travel experts.

Malta

7/21
Still considered an under-the-radar destination for many Americans, Malta has so much to offer. Traveling to Europe in the winter months can help save you some money and it lets you enjoy the sites with fewer crowds, allowing a more authentic experience. And with Malta boasting 300 days of sunshine and a temperate climate, you don't even have to worry too much about bad weather.

Kauai, Hawaii

8/21
When most Americans think about visiting Hawaii, they think about Honolulu and Waikiki, the popular areas on Oahu. But since December is actually the start of Hawaii's high tourist season, it makes more sense to travel to Kauai-the Garden Island-to experience the natural beauty of Hawaii without the crowds.

Langkawi, Malaysia

9/21
Langkawi is actually a cluster of almost one hundred islands in an archipelago off the northwestern coast of Malaysia. It'll take about a three-hour ferry ride to get to the main island, but the views are worth it. Dream Cruises is even offering a stop at the island as part of one of their Southeast Asian itineraries in 2020.

Jamaica

10/21
Jamaica is an ideal island destination if you're trying to plan a multigenerational or skip-gen trip. Skip-gen trips are starting to grow in popularity as parents may not always have the time off from work to take their kids on a vacation. And Jamaica offers the ideal mixture of entertainment with easy access to accommodations for older and younger travelers alike.

Sicily

11/21
Another European island getaway, visitors are sure to get their fill by taking a culinary tour through the island. The island is also becoming widely popular with women-only tour groups. Combine the two for your own version of an 'Eat, Pray, Love" girls trip.

Puerto Rico

12/21
Puerto Rico has been making a comeback after the devastation of Hurricane Maria two years ago. Discover the history of Old San Juan, adventure through the mountainside to see waterfalls and see the bioluminescent beach at night.

Seychelles

13/21
Off the coast of Africa in the Indian Ocean lies the archipelago of 115 islands known as Seychelles. With beautiful white sandy beaches and crystal-clear water, the long flight is definitely worth the visit.

Isle of Skye, Scotland

14/21
If you're an avid adventurer and lover of the cold, the Isle of Skye is where you need to head. This offbeat destination is filled with rugged terrain and dotted with fishing villages. Weather conditions are unusual on this island-it can snow in summer but not always in winter-but with average temperatures in the 30s and 40s, you'll definitely want to bundle up.

Aruba

15/21
Aruba has a booming tourism industry and after just one visit it's easy to see why. This warm-weathered island is surrounded by clear blue seas with lots of ocean activities. Try your hand at windsurfing or snorkeling, or just spend your days relaxing on the white sandy beaches.

Ireland

16/21
It's always a great time to visit the Emerald Isle with its picture-perfect landscapes and some of the friendliest people. Spend your evenings in a local pub listening to live music and enjoying hearty dishes. Travel around the Ring of Kerry, see the Cliffs of Moher and receive the 'gift of gab' by kissing the Blarney Stone outside of Cork.

Guadeloupe

17/21
Guadeloupe is actually made up of twelve islands in the Caribbean, and it has a wide array of landscapes including beaches, mountains and rainforest. Enjoy French-Caribbean cuisine and visit one of UNESCO's top-rated bays in the world.

The Azores, Portugal

18/21
Although it may be a little colder than what you think of an island paradise-with average temperatures in the 50s and 60s-The Azores still make for a great retreat during the winter. You'll have fewer crowds but plenty of scenic hikes, delicious seafood and even some jungle hot springs.

Bonaire

19/21
Located in the Netherlands Antilles in the Caribbean, this Dutch Island off the coast of Venezuela has strong North African influences. Try your hand at windsurfing, go deep-sea diving and get your fill of delicious Caribbean dishes.

Ko Tao, Thailand

20/21
If you're looking for more of a romantic getaway, there's no better island than Ko Tao in Thailand. Less expensive than Fiji or Bora Bora, Ko Tao excels in giving couples the island vacation of their dreams.

Key West

21/21
There's something for everyone in Key West, and best of all, you don't even need a passport to visit. Take a road trip down US Hwy 1 from Miami to the southernmost point in the continental United States or include this as a port of call while sailing on a Caribbean cruise. Try authentic key lime pie-frozen and dipped in chocolate, if you'd prefer-drink from an oversized coconut, visit Hemingway's house and the cats that still roam the estate or just relax at The Waterfront Brewery as you watch yachts sail in and out of the harbor.

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Lauren Bowman

Lauren Bowman

Lauren Bowman is a travel enthusiast. She loves experiencing new cultures, trying new foods, learning about the world around her, and believe it or not, she loves hanging out in airports. Follow her on Instagram/Twitter @lbowmantravels or contact her at [email protected]

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Helping leisure selling travel agents successfully manage their at-home business.

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Agent Specialization: Group Travel

Laurence Pinckney

Laurence Pinckney

CEO of Zenbiz Travel, LLC

About Me