Uncover America’s Secret Winter Wonderlands: 13 Destinations You’ll Fall For
Why do winter vacation planners divide into two tribes: those who chase the snow, and those who run from it faster than a snowman in July? Sharing is caring—especially when what’s being shared is a list of winter escapes so dazzling, even your snow shovel might want to pack a bag. Some of us crave toasty beaches and umbrella drinks, while others hear the call of the slopes louder than a kid spotting fresh powder outside the school window.
The real magic isn’t in the trip you take—it’s in that ritual of plotting, dreaming, and arguing (lovingly, of course) about whether hypothermia or sunburn makes the better souvenir . Kayak’s latest winter getaway rankings are about to make that debate ten times harder. From sun-drenched islands to towns so cozy you’ll want to hug a mug of cocoa and never let go, this roundup is equal parts inspiration and FOMO .
So—whether you’re yearning to ski, snorkel, or just exit the group chat about who’s cooking dinner tonight—get ready. Here are 13 U.S. destinations that promise a winter worth sharing (and, if you’re feeling generous, not just on Instagram) . LEARN MORE
Winter vacations don’t have to mean gray skies and freezing temperatures, unless that’s exactly what you’re after. The U.S. offers a fantastic mix of destinations that cater to every kind of traveler. If you’re dreaming of warm sandy beaches or snow-capped mountains, there’s a perfect spot waiting for you to escape the everyday.
Kayak recently ranked the top winter getaways in the U.S., and the list doesn’t disappoint. From tropical islands to cozy ski towns, these destinations prove that winter can be the most wonderful time of the year for travel. But, of course, every traveler’s dream escape is different, some may want adventure, while others just want to thaw out under the sun.
So, if you’re ready to break out of your routine and embrace the season, here are 13 of the best winter destinations in the U.S. These spots have earned their rankings for good reason, and we’re getting into what makes each one special.
1. Key West, Florida
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Key West is the kind of destination that feels like a world away, even though it’s just a flight (or scenic drive) from the mainland. Known for its crystal-clear waters and laid-back vibe, this tropical paradise is the ultimate escape from the winter blues.
Spend your days snorkeling in the warm ocean or exploring the vibrant streets of Old Town. Don’t miss a visit to Ernest Hemingway’s home or a sunset celebration at Mallory Square. With temperatures that rarely dip below 70°F, it’s the perfect place to leave your sweater behind.
2. Puerto Rico
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If you’re after a destination that blends history, culture, and stunning beaches, Puerto Rico should be on your list. As a U.S. territory, it’s an easy trip with no passport required, yet it offers a tropical vibe that’s hard to match.
Explore the colorful streets of Old San Juan, hike through the lush El Yunque National Forest, or relax on the pristine beaches of Isla Verde. Puerto Rico’s warm weather and lively culture make it a favorite for winter travelers.
3. Big Island, Hawaii
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The Big Island of Hawaii offers a unique mix of adventure and relaxation. With its diverse landscapes, from volcanic craters to lush rainforests, there’s something here for every type of traveler.
Take a helicopter tour over active lava flows or snorkel with manta rays in the crystal-clear waters. Don’t forget to visit Hawaii Volcanoes National Park, where you can witness the raw power of nature up close.
4. U.S. Virgin Islands
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The U.S. Virgin Islands are a slice of paradise that’s just a short flight from the mainland. If you choose St. Thomas, St. John, or St. Croix, you’ll find turquoise waters, white sandy beaches, and endless opportunities for relaxation.
Snorkeling, sailing, and exploring historic sugar plantations are just a few of the activities that await. The islands’ warm weather and laid-back atmosphere make them a winter favorite for travelers seeking a tropical retreat.
5. Nantucket, Massachusetts
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Nantucket may be best known as a summer destination, but its winter charm is undeniable. The island’s quiet beaches and quaint streets take on a magical quality during the colder months.
Holiday events and cozy inns make it an enchanting place to visit in the winter. It’s perfect for those looking for a serene escape with a touch of New England charm.
6. San Diego, California
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San Diego is the place to be if you’re chasing mild weather and endless activities. With its sunny skies and laid-back vibe, it’s a great spot for both relaxation and adventure.
Take a stroll through Balboa Park, enjoy fresh seafood along the waterfront, or soak up the sun on one of its many beaches. San Diego’s year-round pleasant weather makes it a favorite for winter getaways.
7. Orlando, Florida
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Orlando is a winter wonderland for theme park lovers. With fewer crowds during the winter months, it’s the ideal time to visit Disney World, Universal Studios, or SeaWorld.
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