Why You Should Take A Winter Warmup Trip

And how to make the most of it!

By February, the excitement of snow and enjoyment of being holed up indoors during the cold has faded. It’s natural to start getting tired of winter, but for most of the country, it’s far from over.

That’s what makes deep winter the perfect time to give yourself a warm break! Planning a mid-winter trip is a great way to thaw out and break up the cold weather routine.

Maddi is one such traveler that’s a pro at the “winter escape.” We caught up with her about her recent trips, the benefits of heading south, and how to plan the perfect winter vacation. 

Winter in Oregon: pretty but chilly!

Where have you vacationed during the winter and where are you usually traveling from?

I was living in Eugene, Oregon, so I was leaving behind the wet and cloudy Pacific Northwest weather for many of my winter trips. I’ve gone to Cabo San Lucas, Mexico, the Big Island and Maui in Hawaii, and some warm domestic trips, like to San Diego and Los Angeles.

I moved to New York City a few years ago and my first winter trip was to Cartagena, Columbia! Most of my winter trips have been at the end of February because that’s when I start going stir crazy being stuck inside [laughs].

How did this winter travel habit start for you?

Some of my first trips were family trips. My family is from Bend, Oregon, so they often wanted to escape the snow. My brothers went to college elsewhere, so my parents wanted to get us all together and thought, why not somewhere warm? These days, I’ve just kept up the same tradition after realizing how much I loved it!

How do you feel when you first arrive in a new, warmer destination?

Oh, stepping out into a warm, humid climate when you’re coming from cold and rain is such a relief! From the first second in the sunshine, I feel better immediately. Switching my sneakers for some flip-flops that first day is my favorite—Hawaii was especially a welcomed shock.

What about when you return back into winter at home?

Getting some vitamin D has always been helpful. All the trips I’ve taken felt like a reset and I came home ready to take on school or work or the world!

Hikes through the forest are extra satisfying when they lead to waterfalls!

What were some of your favorite activities in each destination?

In Hawaii, it was all about hiking. There’s a gorgeous coastline drive on Maui called “the road to Hana” that takes you to some incredible trails. One of them went through a bamboo forest and we needed to carry our bags over our heads as we crossed a stream to reach a massive waterfall at the end!

Any favs from Cabo?

Yes! I loved the snorkeling there. We also took a glass-bottom boat tour around the famous arches, so we were always looking up at the rock formations or staring down at tropical fish.

The old town of Cartagena Columbia has some of the most lively, colorful streets.

What has been your favorite winter trip overall? 

Cartagena! It’s an incredible, walkable city and I loved trying the new dishes—the ceviche is world famous and the mojitos were so refreshing in the hot weather.

Everyone I’ve told about Cartagena now wants to go. You can just wander the colorful streets and with the lively Colombian culture, there’s always something happening. I feel like there was a band playing on every corner, every night! There’s also an ancient fortress at the edge of the city unlike anything I’d seen.

Even if it’s not hot enough to swim, LA sunsets make the beach better.

Sounds like you’ve done plenty that you wouldn’t have been able to experience at home.

Oh, for sure. All winter, I mostly stay indoors. Being out in nature is super important to me, so that has been one of the biggest benefits of winter travel. 

Even in Los Angeles, it was such a treat to get to sit on the beach with a picnic, even if it wasn’t warm enough to go swimming.

What’s your advice for other travelers looking to plan a winter escape to get away from the cold?

Know what you’re traveling for! I’m usually drawn to the greenery of a destination because that’s what I miss at home during the winter. I also love that I can mix chill beach time with adventures out in nature.

While I do appreciate snow, my ideal place to be is somewhere hot, so I‘ve learned to go even further south than SoCal. Have your checklist and do some research to find a place that’s a perfect match!

So, where to next?

I’m planning on visiting Costa Rica for my next winter trip—it checks all the boxes!