40 Amazing Travel Destinations That Are Perfect for a Winter Vacation ❄️☀️

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Best Winter Travel Destinations

When you need to escape the winter chill, these amazing travel destinations around the world are the perfect place to warm up with sunshine!

When the temperatures drop, most travelers start dreaming of sunshine.

Winter is the perfect time to trade snow boots for sandals in the Caribbean, Southeast Asia, or the South Pacific. These regions are at their peak beauty from December through February.

You’ll find warm seas, blue skies, and plenty of ways to shake off the winter chill.

I love travelling in the winter months. In fact, my first 9 Round-the-World Trips all took place in January and February.

Note: This post may contain affiliate links. If you choose to book through these links, I receive a small commission, which I will undoubtedly blow on more flights (it’s a vicious cycle).  All of this internet voodoo takes place at no additional cost to you. 

Over those years, I quickly became an expert at choosing travel destinations that shine in the Northern Hemisphere’s winter months.

And I can tell you from experience that there’s nothing quite like relaxing on a beach in Thailand while the rest of the world is shoveling snow off their driveway.

Of course, winter also brings magic to places that embrace the cold.

From European Christmas markets to snowy ski resorts in the Alps or Colorado, there’s something special about leaning into the season, too. 

Whether you’re chasing sun or snow, this list of awesome winter travel destinations will help you add a few new places to your Travel Bucket List this winter.

Read More: I’ve Been to 175 Countries. Here are the 50 Best Places to See in Your Lifetime.

From Australia to Zanzibar, here are 40 amazing places around the world to beat the winter blues (or embrace the season, if you must!):

1. Bangkok, Thailand

Bangkok is steamy most of the year, but in winter it becomes pleasantly warm and far less overwhelming.

Winter Destinations Bangkok Thailand
Bangkok, Thailand

From golden temples and the Grand Palace to buzzing night markets and street food stalls, this energetic city is best explored when the heat and humidity are manageable.

It’s also the perfect jumping-off point for Thailand’s islands.

Read More: 3 Reasons Koh Lipe is the Best Thai Island You’ve Never Heard Of

Best Months to Visit: December–February
Where to Stay: Mandarin Oriental Bangkok or The Peninsula Bangkok

2. Maui, Hawaii 

Winter is Maui’s most magical season, when thousands of humpback whales migrate to Hawaiian waters.

Winter Travel Destinations Maui Hawaii
The Grand Wailea Resort – Maui, Hawaii

As a current Hawaii resident, Maui is hands-down my favorite place to be in January and February. Watching whales breach just offshore is a once-in-a-lifetime experience.

Add in warm beaches, waterfalls, and the scenic Road to Hana, and Maui is one of the world’s top winter escapes.

Read More: The Ultimate Guide to Maui Hawaii for First-Time Visitors🌺

Best Months to Visit: December–February
Where to Stay: The Grand Wailea Resort & Spa or Montage Kapalua Bay

3. Antarctica

The only time to visit Antarctica is during the Southern Hemisphere’s summer (December to February) and that’s why it’s the ultimate winter adventure.

Days are long, wildlife is active, and conditions are ideal for expedition cruises.

Winter Travel Neko Harbour Antarctica
Neko Harbor, Antarctica

I know what you’re thinking, isn’t it crazy cold there? Actually, it’s not that cold! In fact, when I visited, it was colder in New Jersey than Antarctica on the days we were exploring this incredible continent.

Read More: Expedition Antarctica: The Bucket List Journey that’s Worth Every Penny

From penguins and seals to dramatic icebergs, an expedition cruise to Antarctica is the closest you’ll probably ever come to visiting another planet.

Best Months to Visit: December–February
Where to Stay: No hotels here! Book an expedition cruise with Quark Expeditions or Hurtigruten

4. Patagonia (Chile & Argentina)

While it’s winter up north, Patagonia is in full summer mode. Long days, mild weather, and open hiking trails make this the best season to explore Torres del Paine, Los Glaciares, and beyond.

Winter Travel Patagonia Chile Lake Pehoe
Torres del Paine National Park, Patagonia

Whether you’re trekking among glaciers or spotting wildlife, Patagonia is spectacular in the winter months. And the all-inclusive Explora Patagonia resort is the perfect home base for exploring Torres del Paine National Park.

Read More: The Luxurious explora Patagonia is the Most Spectacular Way to Experience the Beauty of Patagonia

Best Months to Visit: December–February
Where to Stay: Explora Patagonia in Torres del Paine

5. Australia (Sydney & the Whitsundays)

Australia’s summer aligns with the Northern Hemisphere’s winter, which means it’s prime time to go. Sydney comes alive with festivals, sunny beach days, and nearby National Parks like the Blue Mountains.

Australia Hardy Reef Pontoon Great Barrier Reef
Australia’s Great Barrier Reef

While the Whitsundays offer dazzling turquoise seas and the Great Barrier Reef is at its best. It’s a trip that blends city life with paradise islands.

Read More: This Aussie Archipelago is the Perfect Home Base for the Great Barrier Reef 🦈🐠

Best Months to Visit: December–February
Where to Stay: Park Hyatt Sydney or the Intercontinental Hayman Island Resort

6. European Christmas Markets (Germany)

If you’re traveling around Christmas time, nothing beats the festive magic of European Christmas markets.

Germany Christmas Markets Christkindlesmarkt Nuremberg
Christkindlesmarkt in Nuremberg, Germany

Germany does them best, with twinkling stalls, mulled wine, and fairy-tale backdrops like Nuremberg or Rothenburg ob der Tauber. Bundle up, sip glühwein, and shop for handmade crafts in the glow of holiday lights.

Read More: With a 400 Year History, Nuremberg’s Christkindlesmarkt is One of Europe’s Most Beautiful🎄🎁

Best Months to Visit: Late November–December
Where to Stay: Hotel Drei Raben in Nuremberg or the Hotel BurgGartenpalais in Rothenburg

7. Riviera Maya, Mexico

While much of North America is cold, the Riviera Maya delivers sunshine and turquoise seas. And when it comes to a cheap winter destination with 5-star sunshine, it’s hard to beat Mexico’s Riviera Maya.

Winter Vacation Ideas Mexico Caribbean Tulum Beaches Palms
Tulum, Mexico

This stretch of Mexico’s Caribbean coast is famous for white-sand, beautiful beaches, cenotes, and Mayan ruins. Winter also avoids the peak of hurricane season, making it one of the best times to go.

Read More: Forget Cancun: Why the Riviera Maya is Mexico’s Best Destination

Best Months to Visit: December–March
Where to Stay: Trobbu Boutique Collection Tulum – All inclusive or Palafitos Overwater Bungalows

8. Punta Gorda, Florida

A quieter Gulf Coast alternative, Punta Gorda is perfect for a laid-back winter beach trip. Of course, I might be biased. Because, full disclosure, Punta Gorda is my home town!

Winter Travel Punta Gorda Florida Sunset Waterfront
Punta Gorda, Florida

This charming SW Florida waterfront town sits on Charlotte Harbor with perfect sunsets, easy access to nearby islands, and calm waters for boating or kayaking.

Winter weather here is absolutely magical. That’s why we have so many northerners “snowbird” here every year. The winter months in Southwest Florida bring warm, sunny weather, without the oppressive humidity of the summer months.

Read More: 10 Super Fun Things to Do in Punta Gorda FL (#7 is a Must!)

Best Months to Visit: December–March
Where to Stay: Wyvern Hotel Punta Gorda or the Sunseeker Resort

9. US Virgin Islands

The US Virgin Islands are at their best in winter, when trade winds bring perfect beach weather.

Winter Destinations St John USVI Trunk Bay
Trunk Bay, St John, USVI

St. Thomas, St. John, and St. Croix all shine with white sand, turquoise waters, and lively Caribbean culture. It’s one of the easiest warm-weather getaways for Americans, with no passport required.

Best Months to Visit: December–April
Where to Stay: The Ritz-Carlton, St. Thomas or Westin St. John Resort Villas

10. Singapore

Winter is one of the driest and most pleasant times to visit Singapore. The city sparkles with holiday decorations in December, and its blend of modern skyscrapers and historic neighborhoods is best enjoyed without the year-round downpours.

Winter Destinations Singapore Merlion Marina Bay Sands
Singapore’s Merlion Park

Sip a Singapore Sling at the iconic Long Bar at the Raffles Hotel or take a stroll along Merlion Park. Singapore is a terrific destination on its own or a great stopover on your way to other winter destinations in Asia.

Best Months to Visit: December–February
Where to Stay: Marina Bay Sands or Raffles Singapore

11. The Maldives

The Maldives are pure paradise in the winter months. Clear skies, calm seas, and perfect beach weather make this the best season for overwater bungalows and snorkeling with colorful marine life.

Maldives W Retreat Maldives Overwater Spa Bungalows
W Maldives Resort & Spa

It’s peak season here for a reason—everything looks like a screensaver. If you’ve always dreamed of staying in an overwater bungalow, this is the place for you!

Read More: Is Staying in an Overwater Bungalow on Your Travel Bucket List? Head to the Maldives.

Best Months to Visit: December–March
Where to Stay: W Maldives Resort & Spa or Baros Maldives

12. Zanzibar, Tanzania

Zanzibar’s beaches are postcard-perfect in winter. With dry weather and turquoise seas, this is the time to stroll Stone Town’s spice markets, swim in warm waters, and relax on palm-lined beaches.

Zanzibar Island Sandbar Africa
Nungwi Beach, Zanzibar

It’s also a great season for diving and snorkeling. The Nungwi Beach resort area is the perfect home base to explore.

Read More: Beaches, Spice & Everything Nice – How to Spend 3 Perfect Days in Zanzibar

Best Months to Visit: December–February
Where to Stay: Oasis Blu Beach Resort (Adults Only) or Dhow Beach Boutique Hotel

13. Easter Island, Chile

This remote island in the Pacific is at its best in the Southern Hemisphere’s summer. Easter Island is one of the world’s most unique places to visit.

Easter Island Moai Chile Travel
Moai on Easter Island

The moai statues stand against lush green landscapes, and the weather is perfect for exploring seemingly endless archaeological sites. Zero crowds and welcoming locals make it feel even more special.

Read More: If Easter Island Isn’t On Your Bucket List, It Should Be. Here’s Why.

Best Months to Visit: December–February
Where to Stay: Explora Rapa Nui

14. Casey Key, Florida

Casey Key is one of Florida’s best-kept secrets. This sleepy barrier island has old-school charm, quiet beaches, and family-run inns that feel worlds away from the state’s busier resort towns.

Florida Places to Visit Casey Key Nokomis Florida
Casey Key, Florida

Like the rest of Southwest Florida, the winter months bring mild weather, sunny skies, and the Gulf at its most inviting.

Read More: The Secluded Florida Barrier Island of Casey Key is Home to a Literary Legend (& You’ve Never Heard of It)

Best Months to Visit: December–March
Where to Stay: A Beach Retreat on Casey Key

15. Aspen, Colorado

Aspen is the ultimate winter ski destination in the United States. Powder snow, luxury lodges, and lively après-ski make it a favorite for both skiers and non-skiers.

Aspen Colorado Winter Travel
The St. Regis Aspen

Beyond the slopes, the town’s galleries, boutiques, and restaurants buzz with winter energy.

Read More: Aspen Colorado: Confessions of an Aspiring Ski Bunny

Best Months to Visit: December–March
Where to Stay: The Little Nell or St. Regis Aspen Resort

16. Abu Dhabi, UAE

Winter transforms Abu Dhabi into a comfortable outdoor playground.

Winter Travel Abu Dhabi UAE
Sheikh Zayed Mosque, Abu Dhabi

The scorching heat of summer is gone, replaced by mild days perfect for exploring the Sheikh Zayed Grand Mosque or lounging on Saadiyat Island’s beaches. It’s one of the best times for desert adventures.

Read More: 24 Hours in Abu Dhabi? Here are 3 Things You Can’t Miss!

Best Months to Visit: December–February
Where to Stay: Emirates Palace Mandarin Oriental or Park Hyatt Abu Dhabi Hotel & Villas

17. British Virgin Islands

The BVIs are all about sailing, snorkeling, and laid-back island vibes. In winter, the trade winds make conditions ideal for yachting between islands, and the water is crystal clear for diving.

Jost Van Dyke White Bay Soggy Dollar Bar Caribbean
Josy Van Dyke, BVI

The weather is warm, dry, and perfect for beach-hopping. My favorite spot in the BVI’s is Jost Van Dyke where you’ll find the legendary Soggy Dollar Bar. Home of the original Painkiller cocktail, there’s no better place to soak up the sun in the winter months.

Best Months to Visit: December–April
Where to Stay: Rosewood Little Dix Bay or the Saba Rock Resort on Virgin Gorda

18. Dolomites, Italy

The Dolomites are stunning year-round, but winter transforms them into a snow-draped wonderland.

Winter Travel Dolomites Italy
The Dolomites, Italy

Ski resorts are lively, trails are covered in fresh powder, and the dramatic peaks glow under winter light. It’s one of Europe’s most scenic places for a ski holiday.

Read More: Headed to Italy? Here Are 15 Amazing Places to See from the Alps to the Amalfi Coast 🏔️🍋

Best Months to Visit: December–March
Where to Stay: Forestis Dolomites or My Arbor – Dolomites

19. St. Lucia

St. Lucia is a Caribbean dream in winter, with warm, dry days perfect for lounging on beaches framed by the Pitons.

Saint Lucia Pitons and Champagne
St. Lucia

Saint Lucia is at its most beautiful in the winter months. You’ll find everything from luxury resorts and hot springs to adventurous hikes through the rainforest.

Read More: Why I’m Glad I Gave Saint Lucia a Second Chance

Best Months to Visit: December–April
Where to Stay: Jade Mountain Resort or Sugar Beach, A Viceroy Resort

20. Krabi, Thailand

Krabi’s dramatic limestone cliffs and turquoise waters shine brightest in winter. Clear skies and calm seas make it a prime season for island-hopping, beach days, and exploring caves and lagoons.

Winter Destinations Thailand Islands Maya Bay Phi Phi Islands
Maya Bay, Phi Phi Islands

With less humidity, it’s one of the most comfortable times to be in Thailand. And the resort town of Krabi is the perfect home base to explore. With easy day trips for island hopping, like the Phi Phi Islands and James Bond Island, you’ll have plenty of options for dreamy islands to spend your days.

Read More: 5 Dreamy Day Trips from Krabi that Prove Thailand is Drop Dead Gorgeous

Best Months to Visit: December–March
Where to Stay: Rayavadee on Railay Beach or The Tubkaak Krabi Boutique Resort

21. Boca Grande, Florida

Yes, more of Southwest Florida! Because it really is that perfect in the winter. The charming town of Boca Grande is a quiet slice of Old Florida charm located on Gasparilla Island.

Winter Travel Destinations Boca Grande Island Lighthouse Florida
Boca Grande, Florida

It’s the kind of place where a bicycle or golf cart is all you need to get around. Even in the popular winter months, Boca’s white-sand beaches are peaceful, and the pastel-colored town feels relaxed and uncrowded.

It’s perfect for biking, fishing, and soaking up laid-back island vibes. 

Read More: Forget Naples or Sarasota: Old Florida Still Exists on This Charming Barrier Island

Best Months to Visit: December–March
Where to Stay: The Gasparilla Inn & Club or Boca Grande Hotel

22. Lake Atitlán, Guatemala

If you’re looking for a unique destination to visit this winter, consider this lesser-known region of Guatemala. Ringed by volcanoes and dotted with colorful villages, Lake Atitlán is often referred to as the “Lake Como” of Central America.

Central America Lake Atitlan Guatemala
Lake Atitlan, Guatemala

The lake is truly breathtaking in the dry winter season. Days are sunny and clear, perfect for boat rides between towns or hikes with sweeping views. 

Read More: Go Green with Glamour in Guatemala at Lake Atitlan’s Luxurious Laguna Lodge

Best Months to Visit: December–March
Where to Stay: Laguna Lodge Eco Resort or Tzampoc Resort

23. St. Vincent and the Grenadines

This Caribbean gem shines in winter. Sailing between the islands is the best way to explore unspoiled beaches, turquoise bays, and laid-back towns.

Caribbean Sailing St Vincent Grenadines Tobago Cays
The Tobago Cays

It’s also a great place to learn how to sail if you’ve always wanted to!

Read More: A “Learn to Sail” Caribbean Vacation: From Rookie to Sailor in 7 Days ⛵

The Grenadines are far less crowded than other Caribbean destinations (like the Virgin Islands) this time of year, so a visit here is even more relaxed.

Best Months to Visit: December–April
Where to Stay: Petit St. Vincent Resort or Mandarin Oriental, Canouan

24. El Nido, Palawan, Philippines

El Nido is a tropical paradise of limestone cliffs, lagoons, and white-sand beaches.

Winter Travel Palawan El Nido Harbor Fishing Boats
El Nido, Palawan

Winter falls in the Philippines’ dry season, meaning calm seas and endless sunshine. It’s the perfect time to island-hop and soak up one of Southeast Asia’s most beautiful corners.

Whether you spend your days snorkeling secret lagoons or just lounging on picture-perfect beaches, El Nido is pure paradise in winter.

Read More: The Paradise of Palawan: How to Spend 4 Perfect Days in El Nido

Best Months to Visit: December–April
Where to Stay: Pangulasian Island Resort or El Nido Resorts Miniloc Island

25. Malta

On my winter Round-the-World trips, I always tried to include one European destination. But it’s hard to find a warm location in Europe in the winter months. On RTW #7, I chose Malta, and it was a great pick. 

Winter Travel Europe Malta
Malta’s Blue Grotto

Malta enjoys one of Europe’s mildest winters, so the winter months are a great time of year to go. Sunny days are ideal for exploring Valletta’s historic streets, medieval fortresses, and seaside villages without the summer crowds.

Not to mention Malta’s luxury hotels are a steal in the off-season.

Read More: 5 Reasons Why Malta is Marvelous in the Off-Season

Best Months to Visit: December–February
Where to Stay: The Phoenicia Malta or Iniala Harbour House

26. Cartagena, Colombia

When it comes to warm winter vacations, Cartagena is a colorful gem. The walled Old Town bursts with charm, from cobblestone streets to lively plazas.

Winter Vacation Cartagena Colombia
Old Town Cartagena

Nearby, beaches and islands offer sun and sand. For Caribbean vibes, don’t miss a day trip to the Rosario Islands. Cartagena is one of South America’s best winter vacation spots for culture and relaxation.

Read More: Colombian Charm in Cartagena & the Rosario Islands

Best Months to Visit: December–March
Where to Stay: Sofitel Legend Santa Clara Cartagena or Casa Pestagua Relais Châteaux

27. New Zealand

Winter up north is summer in New Zealand, and that means perfect conditions for exploring both the north and south islands.

New Zealand Queenstown
Queenstown, New Zealand

On the south island, Queenstown buzzes with adventure sports and natural beauty. While up north, the Bay of Islands glows under sunny skies, and Auckland is lively with festivals and outdoor dining.

Read More: How to Spend 4 Perfect Days in New Zealand’s Brilliant Bay of Islands

Best Months to Visit: December–February
Where to Stay: QT QueenstownPaihia Beach Resort & Spa, or Hilton Auckland Princes Wharf

28. Chamonix, France

Set at the foot of Mont Blanc, Chamonix is a legendary ski destination in winter.

Winter Vacation Chamonix France
Chamonix, France

Powder days, dramatic alpine scenery, and a vibrant après-ski scene make it one of Europe’s best winter playgrounds. Even non-skiers will love the Alpine atmosphere in Chamonix.

Tip: Chamonix is also fabulous in the summer months, when I last visited to run the Mont Blanc Marathon (and when this photo was taken). But I have always wanted to go back in the winter!

Read More: France for the Fearless: Chamonix & the Mont Blanc Marathon

Best Months to Visit: December–March
Where to Stay: Hôtel Mont-Blanc Chamonix or the Grand Hôtel des Alpes

29. Kuala Lumpur, Malaysia

Kuala Lumpur is warm year-round, but winter brings drier weather that makes exploring the city’s highlights much more comfortable.

Petronas Towers Kuala Lumpur Malaysia Winter Vacation
The Petronas Twin Towers

From the Petronas Twin Towers to bustling food markets and temples, the city is vibrant and easy to enjoy this season.

Best Months to Visit: December–February
Where to Stay: Mandarin Oriental Kuala Lumpur or The Majestic Hotel

30. Galapagos Islands, Ecuador

Winter is one of the best times to visit the incredible Galapagos Islands for warm seas, active wildlife, and clear skies.

Galapagos Islands Sea Lion Swim Ecuador
The Galapagos Islands

Sea turtles nest, birds court, and marine life is abundant. It’s a living natural wonder that feels especially alive this season. And contrary to popular belief, pricey eco-cruises aren’t the only way to visit the Galapagos.

Read More: How to See the Galapagos Islands on a Budget

Best Months to Visit: December–February
Where to Stay: Finch Bay Galapagos Hotel or Hotel Angermeyer Waterfront Inn

31. Nusa Lembongan, Indonesia

Bali is a world famous winter destination. But to me, nearby Nusa Lembongan island is a more tranquil alternative to Bali. And winter is one of the best times to go.

Nusa Lembongan Dream Beach Indonesia Asia Destinations
Dream Beach, Nusa Lembongan

Dry weather means perfect days for beach lounging, snorkeling, and exploring nearby Nusa Penida. The island feels relaxed and blissfully uncrowded.

Read More: 3 Reasons Nusa Lembongan is the Perfect Escape from Your Bali Vacation

Best Months to Visit: December–February
Where to Stay: Lembongan Beach Club & Resort or 353 Degrees North

32. The Bahamas

The Bahamas are at their most idyllic in winter. With hurricane season behind and sunny, dry weather ahead, the islands are all about turquoise waters and white-sand beaches.

Winter Vacation Nassau Bahamas
Nassau, Bahamas

From Nassau to the Exumas, it’s one of the Caribbean’s top escapes.

Best Months to Visit: December–April
Where to Stay: The Ocean Club, A Four Seasons Resort or Grand Isle Resort in Exuma

33. Corn Islands, Nicaragua

Far off the beaten path, the Corn Islands are a rustic Caribbean escape in winter. Little Corn and Big Corn both offer unspoiled beaches, turquoise waters, and an authentic, laid-back vibe. But Little Corn is the true gem.

Little Corn Island Caribbean Destinations to Visit Nicaragua
Little Corn Island

Flights arrive from Managua on Big Corn Island. From there, you’ll have to take a panga ride to reach Little Corn. Far removed from mass tourism, this tiny, car-free island is the Caribbean of 50 years ago.

And winter’s dry season is the ideal time to go.

​Read More: The Best Caribbean Islands You’ve Never Heard Of: Nicaragua’s Corn Islands

Best Months to Visit: December–April
Where to Stay: Little Corn Beach & Bungalows or Yemaya Reefs

34. Ha Long Bay, Vietnam

Ha Long Bay’s limestone karsts and emerald waters are breathtaking in winter. Cooler, drier weather makes it ideal for overnight cruises through the bays and islands.

Halong Bay Vietnam Winter Places to Visit Asia
Ha Long Bay, Vietnam

It’s one of Vietnam’s most iconic sights, and winter is the most comfortable time to see it.

Read More: Asia with Ease: A Cruise to Vietnam, Cambodia & Thailand

Best Months to Visit: December–February
Where to Stay: Calista Cruise or Orchid Premium Cruise

35. Victoria Falls, Zambia/Zimbabwe

Victoria Falls is awe-inspiring in any season, but winter (the Southern Hemisphere’s summer) brings warm weather and excellent viewing conditions.

Victoria Falls Zimbabwe Zambia Africa
Victoria Falls

Known as “the smoke that thunders,” this natural wonder is at its most dramatic in February, with rainbows often arcing through the mist.

You can view the falls from either the Zambia or Zimbabwe side and it’s easy to cross between the two. When I visited, I chose to stay on the Zambia side but crossed the border to view the falls from the more impressive (and organized) Zimbabwe side.

Read More: Lucky in Livingstone: An Extraordinary Visit to Victoria Falls

Best Months to Visit: January–February
Where to Stay: The Victoria Falls Hotel or Palm River Hotel

36. Roatán, Honduras

Roatán is a diver’s dream, and winter is when its coral reefs are at their most inviting. Warm, clear seas surround this laid-back Caribbean island, which also boasts relaxed beaches and friendly small-town charm.

Roatan RIMS Institue for Dolphins Anthonys Key Resort
Anthony’s Key Resort, Roatan

If you’re a diver or love dolphins, be sure to stay at Anthony’s Key Resort. I did their Dolphin Trainer for a Day program a few years ago, and it’s still one of my all-time favorite travel experiences. 

This Central American island destination is the perfect mix of adventure and relaxation.

Read More: I Visited The Caribbean Island of Roatan to Live Out My Dream as a “Dolphin Trainer for a Day”🐬

Best Months to Visit: December–April
Where to Stay: Anthony’s Key Resort or Grand Roatán Resort

37. Key West, Florida

Key West is lively year-round, but winter brings its best weather. The island’s colorful streets, quirky culture, and sunset celebrations are all more enjoyable under sunny skies and mild temperatures.

Winter Vacations Key West Florida USA
Key West, Florida

Don’t miss a climb up the charming lighthouse or a visit to the Hemingway House to visit Hemingway’s famous six-toed felines. Key West is the ultimate U.S. winter escape for small-town island vibes.

Read More: One Day in Key West, Florida? Here are 7 Things You Can’t Miss

Best Months to Visit: December–March
Where to Stay: Douglas House or Santa Maria Suites Resort

38. ABC Islands (Aruba, Bonaire & Curaçao)

The Caribbean’s ABC Islands are a great place for a winter trip. Like the rest of the Caribbean, winter is peak season here, and the hotel rates reflect that.

Aruba Beaches Beautiful Tropical Places
Flamingo Beach, Aruba

But if you’re trying to escape the winter chill, there’s no better place. Aruba has convenient flight connections from the US and world-class beaches (including one known for a few pink feathered friends!).

Bonaire is a diver’s paradise, and Curaçao shines with colorful Dutch colonial charm. Together, they’re a perfect trio for a Caribbean winter escape.

Read More: Why the Caribbean’s ABC Islands are the Perfect Hurricane-Free Summer Escape

Best Months to Visit: December–March
Where to Stay: Renaissance Wind Creek Aruba Resort (Aruba), Boutique Hotel Bougainvillea (Bonaire), Avila Beach Hotel (Curaçao)

39. Dubrovnik, Croatia

Dubrovnik in winter feels like a secret. The crowds are gone, the weather is mild, and the medieval Old Town glows in peace. This is another European destination I added to my winter Round-the-World #2 itinerary, and it turned out to be the perfect time to visit.

Croatia Dubrovnik Stradun Old Town in Winter
Dubrovnik’s Stradun

Since then, I’ve visited Dubrovnik three more times in the summer months. But the January visit will always be my favorite. 

In the winter months, you can wander the city walls, explore fortresses, and soak up Adriatic views without the summer bustle. Fewer crowds make winter the perfect time to check southern Croatia off your Travel Bucket List.

Read More: In Dubrovnik Summer Sizzles but Winter is Wiser

Best Months to Visit: December–February
Where to Stay: Hilton Imperial Dubrovnik or The Pucic Palace

40. Boracay, Philippines

Boracay’s powdery White Beach is one of Asia’s most beautiful places, and it’s perfection in winter. The skies are clear, the water is calm, and the island buzzes with energy.

Winter Vacation Boracay Philippines
White Beach, Boracay

It’s the ultimate Southeast Asian beach getaway, whether you’re looking for pure relaxation or a little nightlife.

Best Months to Visit: December–April
Where to Stay: Shangri-La Boracay or Discovery Shores Boracay

So book that winter trip now!

Winter doesn’t have to mean cold weather and staying indoors.

Whether you’re chasing sunshine in the Caribbean or Southeast Asia, or leaning into snowy adventures in Europe and North America, this often overlooked season opens up a world of incredible options.

From whale watching in Maui to skiing in the Dolomites or diving in the Maldives, the best winter vacations deliver sunshine, adventure, and a break from the short days of the season.

So instead of hibernating this year, grab your passport and book that dream trip.

Need more travel inspiration? Start here:

20 Dreamy Destinations for a Christmas Holiday Vacation This Season🎄🎁🎅

The Ultimate Guide to Planning the Round the World Trip of a Lifetime

Around the World in 30 Extraordinary Travel Experiences

40 Incredible Fall Travel Destinations to Visit Right Now 🍂

Winter Vacation Ideas
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