top of page

Winter IS coming! Ideas for your Winter Vacation

Updated: Nov 9, 2019

Labor day marks the 'unofficial' last day of summer. But summer weather is still very much upon us. As kids are heading back to school, it’s hard to think past the schedule changes and increased traffic in our day to day. But everyone knows what happens mid-way through winter... you begin to think "I'm sick of winter, will it ever end?"

So place yourself there's a cold, dreary winter night around 5pm and the sun is already down…you are wishing you could be anywhere else to escape the relentless gray weather. Aha! Like a vacation! Having a trip on the books gives you something to look forward to, some excitement to pull you through those cold weeks.

Once the first autumn weather arrives it gets much more challenging to book a winter trip.

The best lodging and flights have already been snatched up. Don’t lose sight of your much-needed winter getaway. This is where we step in!

Here are six ideas in case you need inspiration. We will take care of all the planning and crush the details that can be so challenging. Reach out to us for help using your leftover vacation days!

Escape to Warmer Weather or Embrace the Cold?


Warmer Weather

Warm temperatures, beautiful beaches, and many accessible airports mean Florida is always a popular winter destination. Lodging and airfare therefore book up much farther in advance than most destinations. But c'mon, who doesn't want to experience the Key West vibe in January?


Warmer Weather

Hawaii offers a year-round tropical climate and two extraordinary parks: Haleakala NP and Hawaii Volcanoes NP. But if relaxing on the beach is more your thing, there are plenty of getaways to be had.


Mild Temperatures

In winter Gatlinburg has fewer crowds but no loss in Smoky Mountain beauty, and Pigeon Forge puts on endless holiday activities. And the city of Asheville is just the best (read our blog about Asheville here!). Geographically speaking, choosing the right place to stay will minimize your time in the car and allow you to see more.


Mild Temperatures

For our adventure seekers out there, the national parks are still America's best idea. But in winter they can be challenging to visit, with road closures and weather-dependent activities to name a few. But these magical places reward those who've prepared:

Joshua Tree NP
Joshua Tree National Park


Embrace the Cold

Driving through Kentucky's rolling hills will reveal charming towns and fascinating bourbon history. There's a relatively tight cluster of distilleries between Lexington and Louisville that form the Kentucky Bourbon Trail that make multiple visits easy. But don’t underestimate the logistics…you don’t want to be in your car for hours after drinking bourbon all day!


Embrace the Cold

Are you someone who embraces the cold? There are countless towns in Colorado that have perfected winter entertainment, from skiing to snowmobiling, shopping to bar-hopping. Think Breckenridge, Vail, Aspen. Let us help you spend more hours on the slopes by finding places that have ski-in/ski-out accessibility.

We all deserve to be happy - even during those dreary winter months. So reach out to TripPossible for help planning the stressful details of your winter getaway, wherever it may be. Or if you need some inspiration, give us a call. We've always got some ideas.


bottom of page