5 Exciting Winter Getaways

winter getways

Bundle up!

Gloves? Check. Scarf? Check. Thermals? Double check. Just because it’s winter doesn’t mean you have to stay at home. In fact, we recommend just the opposite: beat the winter blues with a quick trip (or two!).

If a chilly adventure is calling your name, check out our fave winter getaways. Whether you’re up for a city or a ski trip, we’ve got you covered!

  • Chicago, IL

    Yep, it’s c-c-c-c-cold in Chicago in the winter. But you guys, the snow-capped skyline is totally worth shivering for.

    Luckily for even the most intrepid of travelers, many of Chicago’s top attractions are located indoors. The Art Institute of Chicago is especially impressive, with thousands of jaw-dropping works that span genres, continents, and centuries of art.

    But if you really want a taste of Chicago, grab a slice of deep-dish pizza and catch a Chicago Bulls game. You don’t have to be a basketball fan to enjoy the excitement and energy of the notoriously rowdy Chicago fans!

    Best Winter Getaway: to get that big-city buzz

  • Jackson Hole, WY

    Looking for snow action? Then Jackson Hole’s your town: over 2,500 skiable acres, 500+ inches of annual snow on the mountains, and a whopping 4,139-foot vertical drop. Yikes! Not a skier? You can also go tubing, snowmobiling, ice skating, dog sledding, or even take a snow coach tour to nearby Yellowstone.

    Slopes aside, what really makes Jackson Hole one of our favorite winter getaways is its cowboy vibe. Vintage shops sell western gear from blankets to moccasins. Downtown’s historic Town Square, with its iconic antler arches, is full of options for drinking and dining.

    Best Winter Getaway: for getting your cowboy on

  • San Francisco, CA

    The City by the Bay is one of our fave spots any time of the year, but it’s hands-down one of our top winter getaways. And we can sum it up with just one word: whales. Yes, you read that right! During the winter, up to 1,000 migrating gray whales will pass through the San Francisco Bay… each day!

    As for our other favorite things to do in San Francisco… well, let’s just say we never had a bad meal there. From authentic Mexican meals to delicious dim sum to mouth-watering Thai street food, it’s a foodie paradise. And of course, the local wines are there to wash it all down.

    Best Winter Getaway: to eat, drink, and be merry

  • Telluride, CO

    With so many ski towns in Colorado, it’s almost impossible to pick just one! But Telluride is tops our list of winter getaways: gorgeous views, an “everyone’s welcome” vibe, and 148 trails for your winter sports fix. If you need a break from the cold (or the sports), head indoors to one of the many art galleries, concerts, or theatres.

    And here’s something super cool that you can only do in Telluride: eat at one of the highest restaurants in the U.S. That would be Alpino Vino, at an elevation of almost 12,000 feet. They’ll even send their heated snow coach to pick you up at the gondola and drop you off at the restaurant.

    Best Winter Getaway: for laidback snowy bliss

  • Washington, DC

    DC is notoriously gray and gloomy in the winter—the perfect blustery background for our national monuments. This time of year is considered off-season in DC, sandwiched between the holiday visitors and the cherry blossom crowds. Totally worth wearing an extra layer or two!

    For outdoor fun, check out some of the pop-up ice skating rinks along the National Mall. Want to warm up? Head indoors to some of the country’s finest museums and monuments. For the most part, they’re condensed into a pretty small area. Just a short walk from one to the next, so you guys won’t totally freeze!

    Best Winter Getaway: for an American History tour

Of course, all that bulky winter clothes means bulky, heavy suitcases. Avoid the hassle of lugging them around and having to pay extra baggage fees by shipping your stuff with LugLess. For less than the cost of the average checked bag, we’ll get your cold-weather gear to your hotel or Airbnb. No sore back, no empty wallet. Just your coziest sweaters, patiently waiting for you to land.