Tips & Guides

6 Reasons to Take a Trip This Winter

By Bri Hand | Oct 13, 2021
Couple hugging on winter vacation and looking at snow-covered mountains.

For many top destinations, the winter season is considered the “off-season,” or the less popular time to visit. But don’t be afraid to go against the grain! Traveling during the colder months has its perks, such as cheaper costs, fewer tourists, and shorter lines.

If you’re on the fence over those January plane tickets, we’re here to convince you to take the plunge for a winter getaway. Here are six reasons to take a wintertime or off-season vacation this year:

1. Lower prices

The No. 1 reason to skip town come the winter season? Low prices.

Depending on the destination, a wintertime vacation could cut your budget by half. Popular cold-weather sites include the Caribbean Islands, Florida beaches, and prime ski resort towns like Lake Tahoe or Breckenridge. There are also plenty of milder climates and medium-to-small sized cities that receive less dedicated winter traffic, such as:

  • Las Vegas
  • Dallas
  • Nashville
  • Austin
  • Chicago
  • San Francisco
  • Atlanta

Once you’ve got your winter destination, it’s time to score the deals. You can find great price deals across nearly every part of your winter vacation, including:

  • Flights: The busier the tourist season, the higher the plane ticket prices. Many airlines purposefully lower a destination’s ticket prices during the off-season to encourage sales. Mid-January through February is a relatively affordable time to fly. And as always, booking early is recommended for a winter getaway. 
  • Accommodations: You’d be surprised by the seasonal fluctuations of hotel and accommodation prices. In some cities, the difference costs more than $150 per night. By doing some research online, you’re sure to snatch up some less expensive vacancies. 
  • Food and leisure: During peak tourist seasons, everything from walking tours to lunch can cost more. By avoiding the crowds in winter, you have a much higher chance of striking deals for all activities, whether that’s ski resort passes or fishing charter excursions.

2. Fewer crowds

No one likes waiting in line. And, on a well-planned winter vacation, you don’t have to. In fact, 27% of travelers prefer winter vacations for their lack of crowds.

During the off-season, you’re practically guaranteed to face shorter lines across airports, restaurants, and leisure activities. To really maximize your time, stick with these crowd-avoiding tips for winter travel:

  • Book activities early: Don’t leave your itinerary up to chance. If you’re taking a metropolis vacation, see what museum, show, and even restaurant reservations you can make before arriving. For beach and skiing destinations, plan out any outdoor sports lessons or equipment rentals you might need. The more you can book ahead, the better.
  • Stay off the beaten path: Yes, certain attractions are can’t-miss opportunities (you don’t visit Las Vegas without seeing the Bellagio Fountain!). But to avoid crowds, step off the well-trodden trail. Choose the less popular ski slopes, parks, beaches, or restaurants to skip the lines.
  • Drive: If you’re up for a road trip, drive to your destination. A car eliminates the need to use public or group transportation, helping you avoid delays and lines. Also, driving makes it easier to build your own schedule. You can hop between sites and attractions (or even multiple cities) with ease.
  • Pick remote accommodations: The city center might have all the sites and attractions. But for some peace and quiet, book your accommodations in a perimeter neighborhood. That way, you’ll avoid tourist trap hotels and get to see more of your destination.

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3. Warming up your winter

There’s no better medicine for the winter blues than sunshine. Break up the season’s dreariness with a warm-weather vacation. You’ll come back refreshed, relaxed, and slightly more sun-kissed to take on the new year. 

You can always hit up the popular hot spots, from Cancun to Palm Beach. Soak up the sun at any of these warm destinations:

  • Fort Myers, Florida: Temperatures in the 70s and affordable accommodations make Fort Myers a hidden gem and one of the best places to visit in winter. Avoid the Daytona Beach and Orlando crowds while still enjoying the Florida ocean views. Besides swimming at Fort Myers Beach, you can also explore the historic River District, Thomas Edison estate, and Manatee Park.
  • New Orleans, Louisiana: There are more reasons to visit New Orleans than Mardi Gras. Take in this city’s beautiful architecture, delicious Cajun food, and multicultural sites during the winter months, where crowds of partiers won’t block your view. You can even catch special wintertime events like the Sugar Bowl and Celebration in the Oaks.
  • Charleston, South Carolina: The weather may not be tropical in Charleston, but during their dry winters, you can still enjoy the city’s botanical beauty and charming streets. Charleston is also one of the few cities where prices are cheaper around the holidays, rather than afterward. It’s also a popular Valentine’s Day destination!
  • Phoenix, Arizona: Winter is often considered Phoenix’s best season, with citywide festivals and dry, mild heat. Take time to hike the outer city’s breathtaking trails, from Camelback Mountain to Papago Park. Golf players and visual art lovers will also enjoy all this city has to offer. 

4. Embracing wintery wonder

Another way to handle the cold weather? Embrace it! 

Build your own Hallmark-worthy vacation with a trip to a winter wonderland. Whether you’re skiing, sleigh-riding, or simply sightseeing, a snowy vacation at one of these destinations can be just as fun as any beach getaway:

  • Boulder, Colorado: Boulder offers beautiful skiing slopes and mountain views, minus the crowds at Vail and Steamboat Springs. While prices can get expensive, the fresh powder and hundreds of ski trails are worth every penny. And for the less outdoors-inclined, Boulder also hosts its International Film Festival every February.
  • New York City, New York: Winter is New York’s most romantic season, filled with lights, music, and bustling crowds. Catch some world-class entertainment across the city’s many theaters and dance companies, or dive into a cozy bar for a cocktail. And for a picturesque winter photo, head into Central Park or Prospect Park. 
  • Milwaukee, Wisconsin: For a snowglobe scene on a budget, you can’t beat this lakeside city. Milwaukee is like Chicago’s less crowded, quirky little sister, with a robust German culture and plenty of gorgeous Tudor architecture. Take a brewery tour and explore the acclaimed art museum for an authentic experience.
  • Philadelphia, Pennsylvania: To see Philadelphia on a budget, head over during winter. You’ll get to tour historic sites like Independence Hall and the Liberty Bell under holiday lights and snow, all without waiting in line. Don’t forget to get a picture on the Museum of Art’s steps (and channel your inner Rocky!) before heading inside.

5. Authentic experiences 

When you choose an off-season vacation, you’re competing with fewer tourists. That means you have a higher chance of scoring popular bookings, from restaurant seats to tours to museums. All doors are open for you to explore—and that means a more authentic experience.

From extra attention to uncrowded hot-spots, reap all that your destination has to offer with an off-season vacation:

  • Personalized services: During peak season, members of the tourism industry—drivers, concierges, waiters, private instructors—can feel a little frazzled and overwhelmed. But during the off-season, their workload lightens to give you more attention. 
  • Perks and upgrades: That free dessert to celebrate your birthday abroad? An upgrade from economy to business class flights? All of these perks are way more available during the off-season. Don’t be afraid to ask for any potential upgrades to your services. 
  • Local spots: As travelers know, locals point the way to the best sites and stops. And with fewer tourists around, you can observe where the locals really hang out. Get to see a city or town’s real culture without other visitors crowding the view.
  • Better photographs: What’s a vacation without a few good pics? It can be tough to snap an Instagram-worthy shot when dozens of tourists are swarming around. But with fewer crowds, you can get a clear photo in front of the city’s best backdrops.

6. Flexibility

Yes, you should try to plan your vacation ahead of time. But don’t let a schedule ruin the fun. Every trip needs a little spontaneity to welcome any unseen opportunities. 

Off-season trips give you the flexibility to change plans easily. Leave room on your calendar to take advantage of open slots for:

  • Popular restaurants
  • Sightseeing tours
  • Private lessons
  • Accommodation upgrades
  • Car or bike rentals
  • Museum or entertainment tickets

Travel easy this winter with Landing

Traveling is about soaking in the culture and sights of a destination. Take the local experience by traveling during the off-season this winter. 

Inspired to start planning your winter trip? Don’t leave your accommodations for last. 

Landing makes travel easy with fully furnished apartments and flexible leases. And for a five-star experience, our buildings offer top amenities like concierge services, pools, and private gyms. 

Skip the hotel fees and travel in style this winter with Landing. 

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.