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Trip Ideas

11 Warm-Weather Vacations to Take This Winter

Already dreading the seasonal slump? Here, 11 incredible warm-weather winter vacations to plan for when you need to get out of Dodge fast.

P.S. Check out What to Pack for a Beach Vacation before your next seaside getaway!

A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.

See recent posts by Chelsea Stuart

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Cabo San Lucas, Mexico

Just a 2.5-hour flight from Los Angeles, Cabo San Lucas rocks an easy commute and exotic appeal during America’s winter months. While the 20-mile stretch between Cabo San Lucas and San Jose del Cabo is dripping in luxurious hotels that have entertained the likes of Jennifer Lopez, Cameron Diaz, and George Clooney, our favorite sleep is the ultra-romantic Esperanza Resort. Set between bluffs on the Baja peninsula, the secluded casitas, suites, and villas are done up in airy, traditional Baja-style decor with handcrafted Mexican furniture and beds draped with soft linen canopies. If you’re in need of a break from lounging on the beach, Wild Canyon ATVing is certain to get your blood pumping. With a personal guide and your own ATV, you’ll follow routes that whip you between barren desert vistas and beaches stretched along the Sea of Cortez. In town, grab dinner at Los Tres Gallos, an authentic Mexican spot off the beaten path of Cabo’s strip that serves killer pozole, mole enchiladas, and tamarind margaritas in an outdoor courtyard.

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Key West, Florida

Florida as a destination is one of the best winter vacations in America for a reason; with both Atlantic and Gulf of Mexico coastlines, the state is all about the beaches. Skip over Fort Lauderdale and South Beach, however, and hole up at the Ocean Key Resort & Spa, where tasteful island-themed decor and a convenient locale—near Old Town, Mallory Square, and Key West Harbor—set you up for an exceedingly relaxed stay. Right out the hotel’s front door, you’ll want to hit Duval Street, a 1.25-mile stretch through downtown Key West that serves as the epicenter for all things eating, shopping, and drinking. When hunger hits, head for Louie’s Backyard, a cafe-style Caribbean-American restaurant that resides in a Victorian home right on the ocean. No surprise, all of their top-billed plates are seafood, including cracked conch with mango chutney and sautéed gulf shrimp.

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Havana, Cuba

Once you arrive in Cuba, you’ll be in need of a welcome drink. Do so like Hemingway, and head for his favorite bar, Floridita, on the corner of Obispo and Monserrate, and order a daiquiri. For dinner, there’s La Cocina de Lilliam, a lush family-run patio restaurant that has served Cuban favorites—like arroz con pollo, fried green plantains, and tres leches cake—to guests as distinguished as President Jimmy Carter. Not far from Plaza de Armas, Havana’s oldest square, check into the Hotel Florida, an impressive Colonial boutique with 25 rooms surrounding an airy ground-floor courtyard with a retractable glass roof.

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Tenerife, Canary Islands, Spain

Beach bums listen up; Tenerife, the largest of Spain’s Canary Islands, has 42 miles of supreme sand (in black pebble and blonde varieties). RedLevel at Gran Melia Palacio de Isora – Tenerife puts you right near two of the island’s best: Alcala and Los Gigantes Beaches. It also makes a great basecamp for day trips to the crater-, volcano- and petrified lava-filled landscape of Teide National Park. Between refreshing dips in the North Atlantic and driving through the snow-capped peaks of Mount Teide, sneak in a meal at Haydée, where you’ll be served up unique dishes like beet creamy rice, olive octopus risotto, or spicy tuna tartare with cherry sorbet.

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If your idea of an amazing warm weather holiday includes fantastic eats and white sand beaches, set your sights on the French Caribbean isle of Martinique. The enchanting island combines the food, customs, and flair of the French with the Caribbean’s abundance of beautiful landscapes. Explore Martinique’s bustling, postcard-perfect capital, Fort-de-France, stopping to snap photos of its palm-fringed pathways, seafront restaurants, and multicolored homes with balconies overflowing with flowers. After browsing the stalls of fruit and homemade rum at Chez Carole, the cavernous covered market, bring your appetite to the market’s eponymous eatery, where you can dig into the country’s signature codfish fritters, coconut chicken, and succulent stewed octopus. Your digs are the ultra-luxe villas at Le Cap Est Lagoon Resort & Spa, Martinique’s most exclusive resort with a serene oceanfront setting and a extensive roster of water activities (think snorkeling, scuba diving, private boat rides, windsurfing, and paddle boarding).

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Kauai, Hawaii

A warm-weather escape doesn’t necessarily imply lazing on the beach or vegging out around the pool. If you’d rather take to the outdoors and get moving, consider Kauai. The greenest and oldest of the islands, Kauai has towering cliffs, plunging valleys, gushing waterfalls, and verdant hills, making it a destination ripe for outdoor enthusiasts. Start your adventures with a bird’s-eye view of the gorgeous island on a Blue Hawaiian helicopter tour of the Waimea Canyon, then, for an up-close perspective, hike the rugged cliff tops of the 11-mile Kalalau Trail. Want to feel the wind in your hair instead? Opt for a thrilling sailboat ride around the Na Pali Coastline—a majestic series of valleys, fluted walls, and sheer ridges rising thousands of feet from the Pacific. Lay your head at the Lodge at Kukui’ula, a collection of two- and three-bedroom cottages on a 1,000-acre South Shore resort community.

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Palm Springs, California

For years, Palm Springs has been a trendy weekend getaway for harried Los Angelenos in need of sun-soaked R&R. But the stylish desert oasis offers pleasures beyond its sublime weather—specifically, its stunning scenery, kitsch-is-cool architecture, flourishing culinary scene, and boutique hotels. A time capsule of midcentury design, the William F. Cody-designed L’Horizon hotel was once a playground for golden-era Hollywood elite like Marilyn Monroe and Betty Grable. Mix a cocktail in your spacious guest room—a clean-lined space with bespoke and upscale vintage furnishings—then catch some rays around the hotel’s glimmering infinity edge pool. The nearby Aerial Tramway, an 11-minute cable car ride that takes guests a half thousand feet up the sheer face up Mount San Jacinto, is a great way to get a lay of the land, and if that leaves your stomach queasy, we’d recommend strong drinks and nouvelle Mediterranean fare at the Purple Palm.

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Negril, Jamaica

Postcard-perfect sands, a soulful vibe, and easy access make Jamaica the ideal weekend getaway. Ditch the touristy cruise ship ports of Kingston and Ocho Rios for Negril, a quiet beachside town on the island’s secluded western tip. If you’re looking to splurge, go all out with the five-star cliffside pads at The Caves or Rockhouse Hotel (trust us, they’re worth it). And when hunger strikes, tuck into open-fire jerk chicken or lobster with a side of live reggae at the chill, local-favorite spot 3 Dives. Then while away your afternoons next to the turquoise water at Seven Mile Beach with a Red Stripe in hand.

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Panama City

Panama City is a cosmopolitan hub combining 18th-century architecture, world-class art, tropical rainforests, and a diverse foodie scene. Visit the striking Frank Gehry-designed Biomuseo or the popular Miraflores Locks, where you’ll get a behind-the-scenes look at the fascinating workings of the Panama Canal, or hike to the summit of Cerro Ancon, a 654-foot hill overlooking the city. The American Trade Hotel—a collaboration between the Ace Hotel group and the Panama city-based Conservatorio—is set in a 1917 neoclassical building in the historic, rapidly-gentrifying neighborhood of Casco Viejo, putting you steps from some of the city’s best bars and restaurants. But if you’d rather stay close to home, the hotel’s amenities include a louche jazz club, a rooftop pool, and a trendy bar popular among well-heeled expats.

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Hamilton, Bermuda

With its pink-sand beaches, colorful colonial towns, and crystal caves, Bermuda is like a quick trip to the Caribbean. The average fall temps hover in the 70s, the prices drop significantly in the shoulder season and, bonus: it’s only a two-hour flight from the East Coast. Fresh off a $100 million top-to-toe renovation, the Hamilton Princess & Beach Club is the place to check into, with a brand new spa, the island’s only celeb-chef restaurant, Marcus’, plus an impressive art tour of 60-plus on-site contemporary works from the likes of Andy Warhol, Jeff Koons, and Nelson Mandela. But save time to explore the quaint hub of Hamilton by stopping for fresh fish sandwiches (with coleslaw, hot sauce, and raisin bread) at Art Mel’s and a spiked Rum Swizzle ice cream cone at Meltdown. Then, browse the neighborhood boutiques where you can pick up authentic Bermuda shorts at TABS or a hand-carved surfboard at Isolated Surfboards.

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Cartagena, Colombia

South America has its fair share of gems, and Cartagena is definitely one of the prized few. The sultry coastal city is home to kick-ass ceviche, eye-popping architecture, cool art galleries and more. Make Hotel Casa San Agustin your base; inside the 24-room mansion, you’ll find traditional lime-washed stucco with terracotta tiles, bougainvillea, swinging daybeds, and 17th-century frescoes (tip: book suite 102, which has a private terrace and plunge pool). Spend your days ‘gramming Cartagena’s colorful buildings, cobblestone streets, and grand plazas, as well as shopping for bright handwoven bags from the streetside vendors, emerald trinkets at Lucy Jewelry, and high-end clothes, art, and interior design at St. Dom, a concept store for upscale Colombian brands. Whatever you do, don’t leave without tasting some ceviche at either the hidden El Boliche Cebichería or the sleek La Perla (try the sea bass ceviche, Peruvian lomo saltado stir-fry, and suckling pig with polenta). For traditional Colombian lunch, La Mulata dishes up crowd pleasers like grilled shrimp with rice and carne asada with patacones (savory fried plantains). Swallow it down with refreshing coconut water from the street fruit stands, a killer mojito at the old-school Cuban-style La Vitrola, or a lychee spritz from El Baron, which overlooks Plaza San Pedro.

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