Couple wears winter boots together

City Guide

Best Winter Vacations for Couples

By Bri Hand | Oct 14, 2021

Thinking about taking a trip this winter? Winter months are the coziest time of the year, complete with steaming cups of hot chocolate and toasty fireplaces perfect for curling up with your partner for a romantic escape. But, if you and your partner are looking to ditch your cozy abode for a wintertime adventure, there’s plenty to experience around the country, too. 

From snowy mountains to sunny beaches, there’s an end-of-year destination for every couple out there—whether you’re looking to immerse yourself in wintertime activities or escape the snowy blusters for somewhere a bit warmer. Cozy up with the romance of the season with Landing’s best winter vacations for couples, including:

  1. Charleston, South Carolina
  2. San Diego, California
  3. New York City, New York
  4. Miami, Florida
  5. Boulder, Colorado
  6. Tucson, Arizona

Let’s get started! 

1. Charleston, South Carolina

Craving a romantic winter getaway with warm weather, but not up for a beach trip? Travel down to Charleston, a gem of a city tucked away on the Carolina coast and one of the best places to visit in winter

Mild weather, gorgeous architecture, and refined Southern cuisine have made Charleston a winning winter escape destination, especially for couples. You and your partner will be swept away by the charm and beauty of this romantic place. During the winter, there are a few winter activities that you can’t miss:

  • Historic sites: If you and your partner are big History Channel fans, you’ll love Charleston’s ancient relics. Start with a historic walking tour, where you can learn first-hand about Fort Sumter and other Civil War landmarks. Not to mention, the city is filled with stunning pre-Civil War architecture to brighten every stroll you take.
  • Dining: A winter vacation in Charleston means one thing—oyster season. Indulge in this local delicacy by attending an oyster roast or even the Lowcountry Oyster Festival (the world’s largest oyster festival). If shellfish aren’t your thing, you can always enjoy Charleston-style grits, fried green tomatoes, and barbecue during January Restaurant Week

2. San Diego, California

Nothing says “winter getaway” quite like the white-washed beaches of San Diego, right? Located on the Pacific coast, this beachside town has plenty to offer in terms of sun-kissed outdoor activities and trendy to-dos, from cocktail kick-backs to romantic evenings on the beach. 

For couples looking for sunset-dropped photo-ops and oceanside memories, you won’t lack with San Diego as your winter-time destination:

  • Whale watching: Every winter, a cohort of gray whales migrate from the icy waters of Alaska to the glowing Californian shores. Grab your partner and trek to popular whale-watching spots like Scripps Park or Torrey Pines State Reserve to catch a glimpse of whale spouts rising from just beneath the ocean’s surface. Or, opt for a romantic sunset cruise that carries you across the sparkling waters of San Diego’s coastal waters for an experience you whale always remember.
  • Ice skating: For a beach-meets-wintertime paradise, take a walk down to Hotel del Coronado to take a spin on its shoreside ice rink. You and your partner can even reserve a private rink-side lounge that features a roaring fire pit and holiday-themed sips and snacks. The rink is open for late-night skates as well, meaning you and your partner can bear witness to San Diego’s beautiful coastal wintertime constellations.
  • See a theatrical classic: Old Globe Theatre, located within Balboa Park, is modeled after Shakespeare’s Old Globe in London. Over the years, it has hosted a number of acclaimed playwrights and productions, but during the winter months, the theater puts on its annual performance of “Dr. Suess’ How the Grinch Stole Christmas” for a cheery flight into Whoville. Snuggle up with your partner under the dimmed lights of the hall, then take a stroll through the park as a midnight treat.

3. New York City, New York

During winter, New York City transforms into a world of pure enchantment. Snow-capped skyscrapers, twinkling lights, and festive store windows all create a snow globe-worthy scene that’s sure to have you clasping to your partner’s hand more tightly than usual. 

When talking holiday trips for couples, you can’t beat the luxurious metropolitan joy that the Big Apple offers, such as:

  • Ice skating: There’s a reason every holiday movie set in New York has an ice skating scene. It really is that fun! The key, however, is to avoid the crowds. Rockefeller and Bryant Park’s rinks are lively, but Prospect Park and the William Vale rinks offer a little more room to glide with your partner in hand.
  • Live entertainment: Of course, New York City has top-tier live entertainment all year round. But during Christmas, you can see some exclusive holiday shows. Classics like the Rockettes Radio City “Christmas Spectacular” and “The Nutcracker” set a festive mood. You can also check out holiday-themed shows at the Metropolitan Opera, the New York Philharmonic, and many more of the city’s fabulous theater companies.
  • Shopping: Around the holidays, shopping in New York isn’t just an errand—it’s an experience. Catch the stunning window displays, from Herald Square to Columbus Circle (and don’t forget the Macy’s light show!). After gifting your partner with the perfect gift, take a stroll through Central Park to admire the snow-capped street lights and the sparkling city lights. 

4. Miami, Florida

Yes, the excellent beaches and vibrant nightlife scene are Miami’s calling cards. But this multicultural city has so much more to offer, from beautiful architecture to gorgeous parks to delicious pan-Latin food. If you and your partner can’t choose between a tropical or cosmopolitan getaway, this Florida destination has the best of both worlds, offering: 

  • Beaches: In Miami, winter temperatures stay in the mid-70s, aka the perfect beach weather. South Beach is the most popular and stylish scene, with thousands flocking to its white-sand shores—giving “white Christmas” a whole new meaning. More low-key options include Sunny Isles Beach, Bal Harbour Beach, and Haulover Beach.
  • Design District: Sleek buildings, contemporary art, and excellent shopping flesh out this Miami district. This neighborhood is curated for pedestrian enjoyment, with eye-catching stores and public plazas for leisure. Don’t miss the Fly’s Eye Dome for an Instagram-worthy picture. 
  • National parks: Take a breather from the bustling city and explore Miami’s natural side. Just a few miles away, you can see alligators and egrets at Everglades National Park, or watch dolphins and sea turtles swim by at Biscayne National Park.
  • Nightlife: At the end of the day, Miami is for couples who like to party. Like its shores, the South Beach neighborhood has the city’s most fashionable nightlife scene, with enough neon lights and chic clubs to rival any holiday decorations. For a quieter night, hit up the local dive bars and dance halls in Little Haiti, Little Havana, and Brickell.

5. Boulder, Colorado

Nestled within the foothills of the Rocky Mountains sits Boulder, a hippie-turned-hip mountain town known for its ample outdoor activities and luxuriously cozy eats and boutiques. 

During the winter months, you and your partner are bound to find yourselves strolling through a winterland paradise of snow-speckled trees, ice-covered brick bridges, and lamp-lined streets toward your next charming location:

  • Pearl Street: This pedestrian paradise is not for the faint of heart. Its bricked streets are bustling with vibrant street performances (yes, even in the winter months), hopping breweries, and a variety of eclectic art galleries and shops to complete your holiday shopping. Stroll the walkway hand-in-hand after sunset—when you look up, you’ll be greeted by a parade of festive holiday lights in the form of snowflakes and globes, in addition to the valley’s star-filled night sky. 
  • Eldora Ski Resort: Located less than an hour west from Boulder lies Eldora Ski Resort, a favorite among locals and beginners alike for its plushly powdered slopes and relative seclusion from the rest of the range. Rent your transportation of choice, and embark on its 680-acres of skiable terrain for a snow-studded day amid the alpines. 
  • Dushanbe Tea House: You and your companions’ hands and feet are bound to get a bit icy during your stay. Escape the cold within Boulder’s beautifully decorated creekside Dushanbe Tea House. Given to the city of Boulder as a gift from Dushanbe, Tajikistan, the tea house transports you far from the icy foothills just outside its doors. Reserve an afternoon tea reservation for two and enjoy a dining experience complete with dim sum, premium tea selections, and the soothing trickle of its in-house water feature. 

6. Tucson, Arizona

Dry heat, gorgeous trails, and 350 days of sunshine per year? Tucson is a unique warm-weather escape for couples, showcasing the Southwest’s artsy culture and desert beauty. You and your partner should take a chance on this Arizona city’s attractions for a trip that’s equal parts relaxation and inspiration (and, of course, you can’t forget the golf courses!). Check out: 

  • Golf: Whether you’re an amateur swinger or an old pro, Tucson is a prime golfing destination. Pick up a club across 40 major courses, including the acclaimed Lodge at Vatanya and Catalina Course. Your vacation will certainly be up to par!

Find a winter getaway with Landing

Every couple deserves to spend their winter together in style. With Landing, you can spend it in style and ease. Our fully furnished apartments and flexible leases make relocating for the winter months simple—and, with amenities like private gyms, pools, and concierge services, living with Landing is also pretty comfortable, too. 

Check out our housing options across these cities to kick off a wintery season of romance and travel. And, for a limited time, you can save up to $750 on your next Landing during our Fall Promotion. Visit hellolanding.com to learn more!

About the author

Bri Hand

Bri Hand is Landing's Content Marketing Manager. She currently lives in Salem, Massachusetts, with her partner and dog, Arlo, but relishes any opportunity she can to travel so she can try new foods, see gorgeous sights, and daydream about living somewhere new after visiting there for less than 24 hours.