These Warm Weather Vacations Will Get You Stoked to Travel This Winter

Make like a bird and fly south.

a residential street on a tropical island
Wander Caye Caulker in Belize | Aleksandar Todorovic/Shutterstock
Wander Caye Caulker in Belize | Aleksandar Todorovic/Shutterstock

Inside all of us, there are two wolves. One who wants to brave harsh winters with the steadfastness of a hardy Minnesotan, and another who couldn’t give a shit about things like “steadfastness” and would much rather spend winter on a white sand beach in a place like Florida or Puerto Rico, eating fish tacos and sipping drinks garnished with a tiny pink umbrella while top 40s hits play in the backdrop. Today, we choose to feed the second wolf. These warm weather vacations—some a quick flight away, some worthy of a longer trip—will keep your spirits high and your travel itinerary full this winter.

Martin Wheeler III/Shutterstock

trip to Puerto Rico means a 3-for-1 bargain of Caribbean beaches, tropical rainforests, and splendid mountainscapes. While we’re big fans of venturing beyond the island’s capital city—where a heap of wonders await, from bioluminescent bays to damn good street food—when the weather gets cold, nothing quite beats the attractions that make San Juan so special. Not to mention that flights here are often relatively cheap. Stroll through Old San Juan and past the fortresses at Castillo San Cristobal and San Felipe del Morro; check out the beaches at Culebra, a short boat ride away; or take a sail around the island or snorkel off the coast, where the water is clear and the marine life just as brilliant and tropical as ever.

Experience Scottsdale

Scottsdale, Arizona

While most of the US is covered in snow or cloud cover during the winter months, it’s the opposite for the “world’s most Western town” where it’s sunny and 75 just about every day. Around this time of year, Arizonans and visitors alike can enjoy what makes Scottsdale great—resort-hopping, hiking, swimming, horseback riding, strolling hits like Old Town and the Desert Botanical Garden—all without the risk of overheating in the desert heat. Plus, Scottsdale boasts all the luxury of big cities like Los Angeles and New York City with designer shopping malls, high-end restaurants like Fat Ox, and scores of wintertime food festivals, music festivals, and art shows.

walkway leading to a palm-lined beach
The Florida Keys are popular for a reason. | Simon Dannhauer/Shutterstock

Sombrero Beach, Florida

They may be an oldie, but the Florida Keys—with its scuba diving and party spots—are a goodie. (As are the weird, wonderful bars that line the coast on your way down.) Those familiar with beaches in this part of the world know the Keys can sometimes be lacking in tropical sandy waterfront. But those REALLY familiar know about Sombrero Beach, near Marathon at Mile Marker 50 on the Overseas Highway. The beach is often deserted during slow seasons, with nothing but you, the white sand, and the mangroves and palm trees aside the turquoise water of the Atlantic. The beach winds on for a bit, and if you’re keen on spending the day there, you can see the sunrise from one side, then stroll to a rock formation down the beach for one of the best sunsets in the Keys at night.

In the winter, Memphis offers all the revelry with half the sweat. | Tetra Images/Getty Images

Although Memphis in winter isn't necessarily "warm," we'd argue that this still makes a great escape for those who want a high-energy city break with way milder temps than, say, those you'd find in New York or Chicago. One of the great Memphian experiences one can have is strolling down Beale Street on a brisk night and being beckoned inside by a driving blues beat and smoky barbecue. The Delta gets shirt-soaking hot during the summer, making this the finest time of year to experience one of the best music and food cities in America. Tourists aren’t packing the bars, and you can chat with the guy next to you about Memphis, a topic every local loves to discuss until the bartender kicks you out.

Who wouldn't want to winter here? | Orietta Gaspari/E+/Getty Images

Lively, colorful, relaxing Barbados has gotten many a shoutout lately, both thanks to their recent removal of Queen Elizabeth II from her Head of State position (rightly deserved) and due to the fact that they named Rihanna a national hero (also rightly deserved). Here, tourists and locals alike jam the port city, and the smell of fresh seafood and soca music fills the air. It’s a perfect beginning to a night out in Barbados—which absolutely needs to include a trip on the Reggae Bus, an island equivalent to the late-night dorm shuttles you remember from college. They’ll only run you a dollar.

Though the country has produced some renowned chefs, the food here isn’t unapproachable. Sure, you can go high-end for dinner at The Cliff, a fine-dining joint that looks straight out of a Bond film, but you can find just as great a meal from Cuz’s Fish Shack on the beach or Friday nights at Oistins. When you’re not eating, Barbados also has the best surfing in the Caribbean outside of Haiti, and the region’s best circuit racing course at Bushy Park. You can sample rum at Mount Gay, the oldest active rum distillery in the world. Or just lounge at Bathsheba or Bottom Bay, the idyllic picture of relaxing Caribbean beaches.

Luis Alvarado Alvarado/Shutterstock

Tucked away on the southern edge of Guadalajara—one of Mexico’s largest cities—you’ll find a charming community called Tlaquepaque. A bustling residential district, the primary draw is the area’s historic Centro region, which offers an array of delights for the artistically- or food-inclined. An absolute must-see for art lovers is the Galeria Sergio Bustamante, a gallery owned by the renowned Mexican surrealist that becomes increasingly whimsical and magical the further you explore it. Right next door, you’ll find Galeria Ramiro Medina, a sprawling complex where a variety of local artists and crafters offer their wares. Stroll along Calle Independencia to browse the stalls of handicraft vendors, and take a seat at El Parian for some delicious eats and mariachi performances, the state of Jalisco being the country’s capital of mariachi. There are plenty of quality Airbnbs in the area, or you can stay at the beautifully hip La Villa del Ensueno. —Nick Hilden

BlueOrange Studio

Unlike Britain itself, the British Virgin Islands is a sunny, warm paradise not just in winter, but year-round. The islands closely resemble Seychelles, with its coasts lined by giant, sea-worn boulders, its crystal blue waters, and its sand as white as snow—but unlike the far-flung gem of the Indian Ocean, these golden isles only take a few hours’ flight to reach from the mainland US. Hit The Baths in Virgin Gorda to explore the turquoise pools that lie between the park’s iconic towering granite megaliths; sail, snorkel, and stroll in Cane Garden Bay on Tortola; or explore 300+ shipwrecks on Anegada. Oh—and while you’re at it, stay for a night at the Saba Rock Resort, founded by a real-life pirate of the Caribbean.

Mardi gras or no, New Orleans comes alive in the winter. | GTS Productions/

True, there’s not a whole lot underrated about going to the Big Easy for Mardi Gras in February. However, visiting New Orleans in the non-Mardi Gras winter season is a different kind of fantastic: you can take in the culture, architecture, and culinary delights of the city with mild temps and minimal crowds. January brings with it the New Orleans Shakespeare Festival at Tulane, and from Ash Wednesday til Easter, you’ll get to experience the almost oxymoronic sensation of prowling this sensual city during Lent, a period of relative detox among New Orleanians. This is a fine time to go if you don’t need to turn the volume up to 11…or if the idea of big crowds still makes you a little uneasy.

La Paz, Mexico

La Paz, Baja California Sur

The stunning, lesser-known seaside city of La Paz, the capital of Baja California Sur, is a mixture of stark desert plains and sparkling seas. Check into the beautiful new boutique Baja Club Hotel located on the Malecón (or for something a little more rustic, try glamping at Rancho Cacachilas) before heading down to the unspoiled Balandra Beach; considered one of the most beautiful beaches in Mexico, development is forbidden here, meaning there are no buildings for miles here—only pristine white sand and turquoise water. Winter is the season for whale watching on the shores of the Baja Peninsula, the shallow lagoons off the coast of La Paz making the perfect pitstop for gray whales migrating to birth and nurse their calves. Scope out the seas before diving straight into them to swim with whale sharks or to try kite surfing with Evolution Kiteboarding in La Ventana, about 40 minutes south. —Dana Freeman

Discover Grenada

The island of Grenada—where the smell of nutmeg follows the breeze everywhere—spans just 21 by 12 miles, but there are weeks’ worth of experiences to be had: jungle hikes, loafing on silky-sand beaches, roaming past waterfalls, digging into spiced fish for breakfast, dancing to live calypso bands and upbeat soca music. You’ll enjoy the latter after a few rounds of $2 beers, which you’ll order barefoot on a sand-floored bar. Following the smell of barbecue or the call of steel drums will lead you to a buzzing outdoor marketplace near Grand Anse Beach (baptized as "Wall Street" because it’s bookended by banks). At night, vehicles blast music and peddle beverages out of ice chests in pickup beds, starting street parties where locals mingle, dance, and snack on grilled meat. Don’t leave without tasting the hometown dish, oil down, a one-pot stew of breadfruit, cabbage, callaloo, dumplings, fish, okra, and turmeric stewed in coconut milk. —Bruce Northam

You might just get Sifnos, Greece, all to yourself. | Tom Zeman/Shutterstock

Cyclades, Greece

We should start by saying that wintertime trips here aren’t for everyone—you’ll find a lot of restaurants and hotels closed for the season. But if you’re looking for a quiet, lonely stretch of beach, a fishing town where you’ll find lots of fresh octopus and zero TVs, a small but breezy white-walled hotel where you’ll wake to the sound of a donkey braying, then head to the Cyclades in the cold months. Hop on a ferry and begin on Kythnos, where you'll spend a few days before moving along to island-hop between Kea, Serifos, Sifnos… you decide. You do have to do a tiny bit of planning in advance though—meaning, be sure to call ahead to the places you want to stay to make sure you’ll find a hotel that’s open. Some towns may be more or less closed, but you’ll find something the next town over. Or, at the very least, the next island over.

You can just kayak your problems away. | Justin Lewis/DigitalVision/Getty Images

Belize: a country that is so different from most of the US (turquoise waters, private islands for rent!) and yet so similar (same language, same currency!) that we can’t help but fall in love again and again. Although this Central American nation is just a tad bigger than New Jersey, it packs in a whole lot of adventure…and, frankly, much better beaches. You’ll find dense rainforests replete with more than 600 ancient Mayan ruins, as well as with eco-friendly lodges like Sweet Songs and Copal Tree, where the sounds of the jungle will soothe you to sleep each night. Meanwhile, the 406-foot deep, 1,000-foot-wide Great Blue Hole and the Belize Barrier Reef—the world’s second-largest living coral reef—are both meccas for scuba divers. On sea, you’ll be surrounded by over 450 isles and more than 70 types of coral; on land, you can spot everything from howler monkeys to collared aracari. And still, none of it can beat the people-watching that you’ll get during a night out on Ambergris Caye.

Riviera Nayarit, Mexico

Skip Cancún, Cabo, and Tulum in favor of Riviera Nayarit on Mexico’s Pacific coast. Whether you’re at a resort in Punta de Mita, a bohemian surf town like Sayulita and San Pancho, or a laid-back village like Lo de Marcos or Chacala, the 200-mile stretch of beachy coastline really has everything you need for a winter escape. The weather is blissful, with almost no rain until June (somehow, tropical trees grow and vibrant flowers blossom without it). The seafood is so damn fresh—whether you’re tossing back a $1 ceviche tostada or cilantro cream shrimp risotto at a snazzier place like Barracuda. And the wifi is good enough for working remotely. If you need further convincing, take heed from the area’s largest winter residents: humpback whales, who spend the winter off the coast of Islas Marietas, Mexico’s rival to the Galápagos Islands. —Joel Balsam

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