Tropical beach getaway with fun margaritas topped with paper umbrellas, or snow covered mountain peaks and spiked hot cocoa? That’s usually the big question when it comes to planning a winter vacation. This year, my boyfriend and I are torn because both options sound amazing, but for totally different reasons.
Last year, we went to Costa Rica at the end of the rainy season (November) and then spent New Year’s in London and Jersey in the Channel Isles, where the temperatures were surprisingly mild. Looking back, I think for both trips we would’ve preferred to fully commit, with either us soaking up the sun somewhere warm and tropical, or embracing the cold with a beautiful snow-covered getaway where at least we choose to be freezing for the sake of the snow, lol.
I’ve been doing a little research and we are torn between a beautiful, snow-filled trip where we can fully embrace the cold and soak in that small, charming town vibe, or a super laid-back beach vacation where we can explore a little (because we both love a good adrenaline rush). So, here it is: my current 2025-2026 Winter Bucket List ✨Enjoy!
Cold Spots
Leavenworth, WA -> Shock horror! I know, I know – it’s the classic pick. With its iconic Bavarian-style Christmas village, I completely get the hype. The pros are pretty undeniable: there’s a reindeer farm nearby (hello??? Actually reindeer?!), gorgeous snowy scenery, twinkling lights, cozy cabins, and tons of festive events. It would seriously be a dream-come-true kind of vacation. However! The prices for hotels directly in or near the village are no joke and it would probably end up costing less just to fly to Europe, lol.
Jackson Hole, WY -> This is one of those places I’d love to see any time of year but there’s something extra magical about it in winter. Picture snowy dude ranches, wild elk wandering through white fields, and those stunning Grand Teton views dusted in powder – it all just feels dreamlike. This one definitely takes a little more planning from the East Coast, though. Between timing flights, snagging the right deal, and picking the perfect date, it’s not exactly a last-minute getaway…but totally worth the effort.
Stowe, VT -> Vermont is beautiful year-round, but Stowe in winter? It’s basically a snow-globe come to life. I visited in late spring in 2023 and had the best time, but even then I remember thinking, “I need to see this place covered in snow”. From cozy ski lodges and charming inns to the Ice Sculpture Festival, the gondola ride, and Après-ski vibes by the fire, it just seems like the place to sparkle a little brighter under the snow.
Park City, UT -> This one is a newer discovery for me, as I hadn’t really paid much attention to it until I learned it hosts the Sundance Film Festival every January (so soo, right?). But honestly, it looks stunning in the snow (feeling a theme here, lol). Between the world-class ski slopes, cozy après-ski lounges, it feels like the perfect mix of glam and mountain town. You can even try snow tubing, dog sledding, or take a sleigh ride under the stars.
Warm Spots
Cancun, MX -. This may be a little typical from the East Coast but I haven’t been since I was 10, and honestly, I would die for a margarita from a swim-up bar. Between the crystal-clear cenotes, colorful coral reefs for snorkeling, and ancient Mayan ruins like Tulum and Chichén Itzá nearby, there’s so much to do if (and when) we decide to venture beyond the resort. Anywho, Mexico will always rock and I stand by that.
Puerto Rico -> Either the Aguadilla side or the San Juan side would be amazing. I’ve been to San Juan twice and loved it both times – it’s got that lively city-meets-beach vibe with colorful streets, rooftop bars, and endless food spots. Aguadilla, on the other hand, is more relaxed and nature-focused, with cliffside beaches, surf towns, and hidden swimming spots like Crash Boat Beach. Either way, I know we would be able to have an amazing time.
Miami, FL -> Okay, maybe my warm sports are feeling a little basic, but if none of the others work out this winter, Miami will always have my back. A December-February Miami trip is almost guaranteed sunshine, ocean dips, and that fun mix of art, culture, and beach life. Between strolling through Wynwood Walls, hitting the vintage markets, and catching golden hour along South Beach, it’s one of those easy, no-stress getaways where you can dress cute, eat well, and just relax.
So, the verdict? Still undecided! Whether it’s snow boots or bikinis, cozy cabins or swim-up bars, I’m just excited to plan something that feels like a little winter magic. Stay tuned for where we actually end up and let me know your opinions! ✈️🏂⛱️
CZ Approved 
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