Valerie Sacksworth

Valerie from Los Angeles asked November 20, 2014

What are your favorite staycation spots in the winter?

For those who look forward to getting away from the cold, gloomy weather, sometimes a tropical vacation isn't in the cards. If this is the case, what are the best cities around you to have a nice, little winter staycation and why?

General Travel

11 Answers

  • Scott Mahaffy

    Top Answer by Scott M. from Fort Collins

    Several of my favorite staycations are going to The Broadmoor in Colorado Springs, or staying in downtown Denver, going to a sporting event, or the theater, and having a nice dinner and an overnight.

  • Billy Cassano

    Billy C. from Chicago answered

    Last winter I left Chicago on Jan. 4th and went to Peru and hopped around South America until I arrived back in Chicago on April 7th. I have a feeling this is a bit more extreme than what you are looking for.

    I would recommend, San Francisco, San Diego, or Denver. I have never been to Miami or Austin (Texas) but I have heard good things about both cities. I know they are very different cities but could be ideal during winter time.

  • Tania Cypriano

    Tania C. from New York City answered

    MontaukI'm originally from Brazil but I have been living in NY for quite a few years. I have been here for so long that I not only learned to love the local beaches (being a spoiled Brazilian), but to enjoy them even in the winter. This past weekend I was in Montauk and it was beautiful. No crowds, beautiful light in the sky, clean air all around, perfect for hikes. If you don't know about Montauk, please check out for a season we filmed there. Located at the end of Long Island, Montauk has beautiful beaches, fun waves for surfing, amazing seafood, and the best sunsets near NYC- anytime of the year.

  • Thomas Dorsey

    Thomas D. from Los Angeles answered

    I always like a walk along San Francisco Embarcadero, Baltimore Inner Harbor and Chicago Magnificent Mile - never a dull moment.

  • claus andersen

    claus a. from Los Angeles answered

    i love staying long term in Penang because of the variety of high quality cheap food, a good international crowd and a lot of locals who have the same interests as me such as cycling and hiking.

    Love to be in a palce where I mostly hang out with locals that have the same interests as me.

    Recife is another place hwere I love to be because of food, football and a great local music scene.

  • Jacey & Scott Mahaffy

    Trippy Ambassadors are elite members of the community, hand picked to help you travel better!

    Jacey & Scott M. from Fort Collins answered

    I adore Steamboat Springs. It's a much more laid-back mountain/ski town that is set in just a beautiful valley. The town itself is nestled next to a river and has a vibrant, quaint downtown with great restaurants and shops. Add a roaring fire to my staycation with a glass of red wine and I'm happy!

  • Claire Wood

    Claire W. from Los Angeles answered

    San Antonio for a nice 'staycation'; five hours from Fort Worth, and warmer in the winter. There is a lot to see and do there; SA is much more than the Alamo. The Riverwalk, Zoo, Museum of Art, Botanic Gardens; balmy weather, wonderful food. There is even a big amusement park similar to Six Flags

  • Morgan Tidwell

    Morgan T. from Los Angeles answered

    Barbados or any island in the Grenadines

  • Robert Fernandez

    Robert F. from Las Vegas answered

    Favorite sports, I have several of them for several reasons. When I travel I like to feel at home because I love to cook. Of course, I do visit several restaurants, but sometimes i just don't want to leave the Hotel/Resort and I BBQ there, or make a fast meal. My Favorite spots Lake Tahoe and Brian Head because I like to snowboard.

    Of Course, California (SoCal) is another great escape during winter time. I escape to Capistrano Beach . If it's not the beach, it is hiking in Arizona, for example Sedona or Scottsdale

    Sometimes I like to be a tourist in my own City, Las Vegas I like to stay at the strip, close to everything.

    Florida is another great escape from the cold. Especially if I want to visit Theme Parks.

    St Maarten is awesome! my favorite spot when it comes to the Carribean.

    I have so many favorite destinations, I could give you a huge list. but these are my favorites within and close to the United States.

  • Joanna Lai

    Joanna L. from Oakland answered

    If you're in California and like the outdoors, I'd chose a place along the coastal Highway 1. Big Sur and Monterey are beautiful. Near Monterey are Carmel and Pacific Grove, which have local shops, places to walk around, etc. There's lots of state parks in the area. It's a great place to unwind.

  • Roxanne Cormier

    Roxanne C. from Montreal answered

    Anywhere carabean. But I prefer Martinique. A french overseas department, it is, for me, the best island. The people are friendly and willing to teach you about theire customs. They are aslo eager to learn about your's.