There are winters when staying home feels right. And then there are winters when you wake up, look at the gray sky, and think, I could be in a swimsuit by tomorrow afternoon. If you are craving that kind of mood shift, the kind that only sunshine, saltwater, and a fruity drink can deliver, these four destinations make it surprisingly easy.
Cancún, Mexico
Cancún is the classic winter escape for a reason. Winter brings some of the best weather of the entire year here, with daytime temperatures in the high 70s to low 80s, low humidity, and water warm enough to float in for hours. The beaches unfurl in long stretches of pale sand, the Caribbean glows in turquoise layers, and everything feels relaxed in that distinctly Mexican way that instantly lowers your stress levels.
Most travelers stay in the Hotel Zone, where the resorts sit along postcard-perfect beaches with huge pools and easy access to the water. If you want something quieter, Costa Mujeres to the north offers calmer beaches and newer resorts, while Downtown Cancún is the best place for a more local, budget-friendly stay. Food is a treat no matter where you land. You can go from polished dinners along Nichupté Lagoon to simple, perfect street tacos in El Centro, where churro stands and fruit vendors linger long after sunset.
The magic of Cancún in winter is that many adventures are close by. Isla Mujeres is a quick ferry ride away and perfect for an easy beach day or scooter ride to Punta Sur. Snorkeling at Punta Nizuc offers calm seas and underwater museum sculptures. And the cenotes between Cancún and Puerto Morelos stay comfortable year-round, with clear freshwater pools that shimmer in the sun. If you book in early December or late January, you get the best prices, lighter crowds, and exactly the kind of sunshine you thought you had to fly much farther for.
What to Pack for Cancún
- Lightweight clothing you can mix and match
- Swimwear (bring more than one set)
- Reef-safe sunscreen and a wide-brimmed hat
- A rash guard or long-sleeve swim top for sun protection
- Comfortable sandals and water shoes for cenotes
- A light rain jacket for occasional passing showers
- A small daypack for ferry and beach trips
Palm Springs, California
Palm Springs feels like it was invented for people who love winter sunshine but hate sweating through a heatwave. Winter temperatures settle into the 70s during the day, which means pool time, patio dining, vintage shopping, and mountain views all within a few square miles of one another. The whole city glows in soft desert light, especially in the mornings when the mountains look painted and the palms sway just enough to remind you this is absolutely not jacket weather.
Hotels here are part of the experience. You can go full retro at The Saguaro, with its rainbow exterior and lively pool scene. The Ace Hotel draws a young, creative crowd with fire pits, music, and one of the most social pools in the valley. If you prefer something quieter and more romantic, Korakia Pensione brings Moroccan and Mediterranean influences to a setting that feels like a private hideaway.
The food scene leans casual but stylish, with brunch at Cheeky’s being almost a rite of passage and dinner at Tac/Quila offering upscale Mexican dishes that pair beautifully with the golden hour light. After dark, tiki cocktails at Bootlegger Tiki make the whole evening feel like a retro palm-frond dream.
Winter is also the best time to explore the desert beyond town. The Palm Springs Aerial Tramway whisks you from the valley floor into the mountains for sweeping views, while Joshua Tree National Park is less than an hour away and perfect for easy winter hikes among its world-famous boulders. The combination of sunshine, design, food, and nearby nature makes Palm Springs one of the easiest winter escapes in the country.
What to Pack for Palm Springs
- Swimsuits, sunglasses, and a hat for long sunny days
- A light sweater or jean jacket for cool desert nights
- Cocktail-casual outfits for dinner and drinks
- Comfortable sneakers for walking around town
- Hiking shoes or trail runners for Joshua Tree
- Sunscreen for those 300-plus days of sunshine
Madeira, Portugal
Madeira is not technically tropical, but it feels like spring every month of the year, which makes it an absolute gift for winter travelers. Winter temperatures usually sit in the mid-60s to low 70s, warm enough for cliffside walks, garden exploring, oceanfront cafés, and those dramatically carved volcanic landscapes that make Madeira feel like its own lush universe floating in the Atlantic.
Most travelers stay in Funchal, a coastal city with charming squares, palm-lined promenades, and restaurants serving everything from fresh seafood to bolo do caco, a traditional Madeiran flatbread served warm with garlic butter. Many of the island’s most beautiful hotels are converted quintas, old manor houses transformed into boutique stays with sea views and terraced gardens. If you want something more secluded, Ponta do Sol and Caniço offer cliffside hotels where balconies hover above the water and the sunsets feel cinematic.
Madeira’s attractions lean outdoors, and winter makes them even better. Levada walks, the island’s scenic trail system that follows old irrigation channels, are cool and peaceful in the winter months. Cabo Girão, one of the highest sea cliffs in Europe, offers glass-floored viewpoints that make your stomach flip in the best way. And the natural lava pools of Porto Moniz stay open year-round, though winter waves sometimes splash dramatically against the edges, adding to the atmosphere even if you stay dry.
With affordable flights from mainland Europe and a gentle climate, Madeira is one of those places you visit in winter and immediately consider returning to every year.
What to Pack for Madeira
- Breathable layers for spring-like weather
- A light waterproof jacket for occasional mountain showers
- Comfortable walking shoes (essential for levadas)
- Swimsuit and water shoes for natural lava pools
- A light sweater or cardigan for cooler evenings
- A reusable water bottle for hiking days
Key West, Florida
Key West is effortlessly warm in the winter, with sunny days in the 70s and breezy nights that feel tropical but comfortable. It is one of the easiest warm-weather escapes in the United States, and it has a personality all its own. Between the pastel houses, roaming roosters, and streets lined with independent cafés and quirky shops, the island feels playful, lively, and relaxed all at once.
Staying in Old Town puts you in the middle of the island’s best walking streets, with charming B&Bs tucked into historic homes beneath flowering trees. Waterfront resorts offer larger pools and sunset-facing balconies, while boutique inns near Duval Street are perfect if you want nightlife within a few blocks.
Food in Key West ranges from indulgent brunch at Blue Heaven, where chickens wander between the tables, to elegant dinners at Latitudes on nearby Sunset Key. If you want something casual, Garbo’s Grill serves incredible fish tacos and burritos from a simple food truck with a strong local following.
There is plenty to do besides eating, too. Key West’s version of winter involves snorkeling over the Florida Reef, wandering through the Hemingway Home alongside its famous six-toed cats, exploring state park beaches, and ending the day at Mallory Square, where the entire island gathers to watch the sky turn gold and then pink. The island is compact, walkable, and cheerful, which makes it ideal for a last-minute getaway when you want warm weather without international flights or jet lag.
What to Pack for Key West
- Light, airy clothing for warm days
- A sweater or denim jacket for breezy evenings
- Two or more swimsuits so one can dry
- Sandals for everyday and water shoes for snorkel trips
- Reef-safe sunscreen and a brimmed hat
- A crossbody bag or small backpack for biking around the island
