I’m a Travel Editor—These Are 6 Winter Vacations To Book Now

A Sun-Soaked Escape in Anguilla

Anguilla

Despite its small size, Anguilla boasts 33 white-sand beaches (including Rendezvous Bay and Shoal Bay) that regularly land on lists of the world's best. By choice, the island has banned large-scale cruise tourism, which keeps its shores peaceful, upscale, and luxuriously quiet. It sits just east of Puerto Rico and about 12 miles north of Saint Martin, both of which serve as the main hubs for visitors flying in.

Where to stay: Aurora Anguilla Resort & Golf Club is the kind of place where everyone in your group gets exactly what they want, whether you're traveling with your partner, your best friends, or three generations of family. Aurora sits right on Rendezvous Bay, and most rooms face the sea, so you wake up to clear, blue water and the kind of quiet island energy that makes you relax the second you arrive.

Rendezvous Beach is the resort's serene, elevated enclave, with elegant sea-front suites and multi-bedroom villas, a sweeping pool, and the Sorana Spa for a well-earned hour to yourself. Over at Merrywing Bay, book an island- or ocean-view room in the Merrywing Tower, or a junior suite with skyline views toward St. Maarten. Traveling with a big group? The private estate homes come with their own pools, dedicated butler service, and full concierge support, basically a house that runs itself so nobody has to play cruise director. (And if kids are along, there's a kids' camp too.)

Where to eat: Aurora grows much of what it serves in a 10,000-square-foot hydroponic garden, so the produce, herbs, and fruit on your plate were likely picked that morning. For a dressed-up night out, D. Richard's is the island's only steakhouse, and the steak Diane is worth building an evening around. Tokyo Bay serves modern Japanese, from sushi to teppanyaki. And C Level, the beachfront restaurant, does a lobster BBQ overlooking Rendezvous Bay that might be the best sunset dinner you have all year.

What to do: Golfers can book time at the acclaimed Aurora International Golf Academy, with sweeping Caribbean Sea views whether you're a beginner or a scratch golfer. Spend an afternoon floating the lazy river and riding the waterslides at Aurora's Entertainment Park from the comfort of a private cabana, or book a private catamaran sail along the coast with swimming, snorkeling, and a lazy lunch on deck. (Sea turtles are everywhere.) The resort's programming also includes horseback riding, fishing in the bay, rock climbing, HIIT and boot camp classes, hydroponic farm and flora-and-fauna tours, glow-in-the-dark mini golf, and s'mores on Rendezvous Bay Beach.

Why book for winter: Aurora is giving the holidays a Caribbean twist with its "Moments of Wonders: A Sun-Soaked Christmas" celebration, running December 21 through January 3. Expect Christmas Eve lobster BBQs on the beach, festive Christmas Day dining, steelpan music, and a New Year's Eve party with a live concert and fireworks. Between celebrations, there's a full calendar of golf clinics with PGA pros, pickleball tournaments, sushi masterclasses, yoga, and more. If you've always dreamed of a warm-weather Christmas, this is it.

A Mountain Getaway in Jackson Hole

Jackson Hole

For snowy-mountain magic, few places beat Jackson Hole, where the Tetons tower over cozy saloons, world-class skiing, and wildlife you'll actually spot from the road.

Where to stay: Hotel Terra Jackson Hole recently unveiled a new renovation that pairs modern amenities with cozy rustic charm. Its upgraded suites come with full kitchens, dining areas, and spacious living rooms with gas fireplaces, ideal for bachelorette trips, milestone birthday getaways, or a group ski week. Add in views of the Teton and Gros Ventre Mountains, the Chill Spa with its rooftop hot tub, and easy access to dining and shopping at Jackson Hole Mountain Resort, and you've got a stylish basecamp just one mile from Grand Teton National Park.

Also at Jackson Hole Mountain Resort, Teton Mountain Lodge & Spa offers elegant, mountain-chic rooms and suites with stone gas fireplaces, whirlpool tubs for soaking after a day on the slopes, and the full-service SpaTerre, all steps from the resort's aerial tram and a short drive from Grand Teton National Park.

Where to eat and drink: For a truly only-in-Jackson-Hole treat, ride the aerial tram up to Corbet's Cabin for "Top of the World" waffles and 360-degree views of the Tetons. Pick from classic toppings like Nutella, brown sugar, peanut butter and bacon, or fresh berries (or order a few to share). Made fresh daily at 10,450 feet, they're the ultimate high-altitude reward.

Also within the resort, grab a bite at the iconic Mangy Moose. Standouts include the house-made game chili, scratch-made shareables, and David's Chopped Salad with wild-caught salmon, named after co-owner David Yoder. Afterward, head into the legendary adjoining saloon, widely celebrated as one of the best Western bars in the U.S., with live music year-round.

At Spur Restaurant & Bar, Executive Chef Andrea Bolanos brings an international twist to the American West with meticulous, from-scratch cooking, including in-house butchery, custom sausage casings, and house-made kimchi and kombucha. Dinner ranges from delicate Ahi Tuna Tacos with avocado and soy vinaigrette to a hearty Tomahawk Pork Chop with herb-roasted fingerlings and an apple cider reduction. Seafood lovers should try the Corn Crusted Red Trout with couscous and lemon beurre blanc, or the Skuna Bay Salmon with harissa beluga lentils and charred chive oil.

Downtown, just steps from Jackson's iconic Town Square, The Bistro brings Parisian brasserie charm to the heart of Wyoming. Go for classics like French onion soup (perfect on a snowy day) and a Croque Madame, or come back for dinner and elevated bistro bites. Start your morning at Persephone Bakery with fresh coffee and a just-baked pastry, then end your night at the Million Dollar Cowboy Bar. Saddle up on one of its famous saddle-horn bar stools, order a round, and two-step your way across the dance floor.

What to do: Ski, snowboard, and ice skate at Jackson Hole Mountain Resort, then book a winter safari with Jackson Hole Wildlife Safaris to two nearby national parks. Naturalist guides track moose, bison, and bighorn sheep through Grand Teton National Park, then take you by horse-drawn sleigh into North America’s largest wintering elk herd on the National Elk Refuge. Want more? From December through March, book a private snowcoach or snowmobile day tour into Yellowstone National Park, gliding through snowy wilderness all the way to Old Faithful.

All-Inclusive Wellness One Hour From San Diego 

Tecate, Mexico

Where to stay: One of my favorite places in North America is Rancho La Puerta, a family-owned wellness retreat tucked into the mountains of Baja California, Mexico. It was was most recently named the #1 International Wellness Retreat in Travel & Leisure's 2026 World's Best Awards. After a seamless pickup at San Diego International Airport and an easy border crossing, you're transported into 4,000 acres of gardens, mountains, and total beauty.

Once you check in, everything from meals to fitness and wellness classes is included. It sounds like a small thing, but removing the constant mental math of vacation spending can feel unexpectedly freeing. No splitting checks, no deciding whether something was "worth it," no pulling out a credit card after every activity.

What to eat: Breakfast and lunch are colorful buffets filled with produce harvested from Rancho La Puerta's own Tres Estrellas Organic Farm, fresh tortillas, nourishing soups, goat cheese made from the goats on the land, and wild Alaskan salmon grilled outdoors. Every meal is built around seasonal, nutrient-rich ingredients like protein, fiber, fresh vegetables, probiotics, and whole grains. By the end of the week, you'll genuinely feel lighter and more energized.

What to do: Every morning starts with an optional guided hike on Mount Kuchumaa, where you'll wind through oak groves and wildflower meadows into the dramatic, boulder-covered foothills. My favorite is the garden hike to the Ranch's La Cocina Que Canta culinary center, where breakfast and a garden tour awaited. Whether you want an easy nature walk, a trail run, or a challenging climb, there's something for every fitness level.

There's also pickleball, restorative experiences like Feldenkrais, sound healing, and aerial yoga, and more intense workouts like Barre, HIIT, and TRX. Don't miss Disco Dance with Manuel. I honestly can't remember the last time I laughed that hard.

Classes and workshops run all day, from yoga, meditation, and salsa dancing to strength training, songwriting, and a new longevity track, so it's impossible to get bored. But you could also skip all of it and spend the afternoon stretched out by the pool with a good book. That's the beauty of an all-inclusive wellness retreat: your days are entirely yours to shape. And if relaxation is calling, the spa offers everything from Watsu and reflexology to massages and Reiki.

A Creative Girl's Trip in a European Dupe

St. Augustine, Florida

The nation's oldest city is a mild-weather winter escape packed with history, craft cocktails, and hands-on creative experiences, which makes it perfect for a girls' trip or a creatively curious solo getaway.

Where to stay: AC Hotel St. Augustine Downtown is a modern waterfront home base where European-inspired design meets St. Augustine history. It's an easy walk to the historic district, and its Riberia Street location puts you right near the distillery and Ice Plant.

Where to eat and drink: Start with a tour and tasting at St. Augustine Distillery, a craft distillery housed in a restored historic ice-plant complex. Then move next door to Ice Plant in the adjacent 1927 industrial building for farm-to-table fare and carefully made cocktails with fresh juices, house syrups, and bitters. For an afternoon sip, San Sebastian Winery offers tours and tastings seven days a week in a former Henry Flagler East Coast Railway building; stay for dinner at La Cocina at The Cellar Upstairs if timing works. Book brunch at MICHELIN-recognized Sunday, and save room for dessert from Cookiebird.

What to do: Sit for a handmade historic portrait at St. Augustine Tintype, a one-of-one keepsake from your trip. Take a slow stroll through the historic district and look beyond the standard landmarks for courtyards, wrought iron, historic storefronts, and old-world textures. Browse vintage and secondhand finds at Graet Goods, then try a hands-on pottery or screen-printing workshop at Make Space (subject to availability), a great skillcation-style experience. Finish by wandering the Abbott Tract Historic District, including a stop at Spinster Abbott's for a photo booth and tarot-card-machine moment.

A Dreamy All-Inclusive Family Getaway in Turks & Caicos

Beaches Turks & Caicos

If your winter trip includes little ones, Beaches Turks & Caicos is a dreamy five-star experience, and was named the Caribbean's Leading All-Inclusive Family Resort by the World Travel Awards. It sits on famously powdery Grace Bay, where the water is the clearest turquoise you'll ever see.

Where to stay: The resort is divided into themed "villages" with Caribbean, Italian, French, and Key West vibes, each with its own pools and suites. The newest Treasure Beach Village offers concierge and butler-level suites and villas, but you can hop around the each of the villages during your day.

What to do: You can spend your days lounging on the peaceful Grace Bay and bring the kids along to the Pirates Island Water Park, a 45,000-square-foot playground with slides for every size, a lazy river, splash pads, and a surf simulator. Little ones get Caribbean Adventures with Sesame Street, from breakfast with Elmo to character parades, and the Kids' Camp covers everyone from infants to teens. That frees up the grown-ups to sneak off for scuba diving, Hobie Cat sailing, or a spa treatment. Off-resort, hop on an Island Routes catamaran cruise to coral reefs, anchor by a secluded white-sand cay, and explore Half Moon Bay in search of rock iguanas (there are many). On the way back, plunge down the boat's 8-foot tube slide into the warm sea.

Where to eat: Graze your way across roughly 20 restaurants, from a '50s-style diner to Caribbean food trucks. Two favorites: Butch's Island Chophouse, a high-end steakhouse with an elevated kids' menu (think roasted chicken and steak frites), and Kimono's, an interactive Japanese hibachi spot where kids can help the chef while everyone sings along to '90s hits.

Why book for winter: When the holidays arrive, the resort goes all in on The Elf on the Shelf, with Scout Elf–themed parties, pajama storytimes, holiday karaoke, and Santaverse movie nights under the stars with fresh popcorn. You can even book The Elf on the Shelf Caribbean Vacation Suite, decked out in the Scout Elf's signature red and white with custom wallpaper of elves lounging among palm trees, themed bedding, a twinkling Christmas tree, and a kids' bunk room stocked with plush Scout Elves, storybooks, and holiday board games. It comes with a Jingle Shell Butler on call around the clock, who leaves turndown treats like mini milk and cookies for your family's very important elf.

A Wellness Reset in the Desert

Scottsdale, AZ

Winter is prime time in the Sonoran Desert: sunny days, crisp nights, and a holiday light show you have to see to believe. Split your stay between a laid-back wellness resort and a buzzy downtown hotel for the best of both worlds.

Where to stay: CIVANA Wellness Resort & Spa is a serene desert escape that feels both luxurious and down-to-earth. Think of it as comfort wellness, a place where you can sip a hot chocolate or a cocktail and still feel like you're doing something good for yourself. Whether you're all about yoga and hiking or just need to unplug by the pool, you can do wellness your way. Most classes are included in the price of your stay, which makes it an affordable and deeply rejuvenating option. Think chakra-balancing meditation, floating sound baths, and an Uplift Aromatherapy Massage that smells like pure joy.

For a little downtown luxury, check into The Scott Resort & Spa in Old Town Scottsdale. With its Havana-meets-California style, a sand-bottom pool, and the dreamy La Vidorra Spa, it's the perfect mix of playful and serene.

Where to eat and drink: Head to the Kierland Commons shopping district for dinner at Zinc Bistro, one of Arizona's favorite French restaurants, known for its nostalgic Parisian cafe vibes. Chef Matt Carter's menu puts an inventive twist on classic French dishes, and it was one of the best meals my travel companion and I have ever had, including in France!

In Old Town, lunch at The Herb Box is a must for seasonal, flavor-packed plates like Grapefruit and Sugar Charred Salmon or Butternut Squash and Corn Enchiladas. Wine lovers should stop by the Los Milics Vineyards tasting room for its award-winning wines; Arizona's wine scene is one of the most exciting up-and-comers in the country. Then end the night at FnB, a cozy downtown gem where James Beard Award–winning chef Charleen Badman serves some of Arizona's best farm-to-table fare alongside exceptional local wine. The menu changes daily and you honestly can't go wrong, but we devoured the roasted rutabaga with ginger crème fraîche, roasted chicken with mustard-crisped spätzle, and fresh pasta with sausage and winter squash.

What to do: Design lovers shouldn't miss Taliesin West, Frank Lloyd Wright's desert masterpiece and a UNESCO World Heritage Site; grab headphones for the self-guided audio tour. Spend a day browsing Old Town's shops, then hop on an e-bike tour with Cliff Creek Outfitters along the Indian Bend Wash Greenbelt, a multi-use path winding past golf courses, parks, and lakes. And book a session at Shanti Sound, where owner Cary Ballou leads 60-minute sound baths that feel like therapy for your nervous system. We left feeling transformed.

Why book for winter: Christmas at the Princess turns the 65-acre Fairmont Scottsdale Princess into a 17-million-light winter wonderland, and it's become one of the country's most spectacular holiday resort experiences. Highlights include:

• Two miles of lights wrapping the four-story Enchanted Plaza tree, plus twinkling desert gardens and illuminated lagoons
• A 120-foot Ferris wheel, the largest traveling wheel in the country, with panoramic views of the resort and McDowell Mountains
• A 6,000-square-foot outdoor rink with real ice beneath the desert sky
• 128 fire tables and private igloos, from Château Champagne's private holiday retreat to cozy, alpine-inspired Village Igloos
• Nightly light shows, festive dining, two Santa experiences, seven Christmas characters, and s'mores by the fire