Why You Should Consider a Winter Escape

And tips to maximize your experience!

By February, the thrill of snowfall and the cozy feeling of staying inside during the cold months start to wear off. It’s normal to feel a bit weary of winter, yet for most parts of the country, the cold season is far from over.

That’s precisely why deep winter presents an ideal opportunity for a warm getaway! Organizing a trip in the middle of winter is a fantastic way to warm up and disrupt the monotonous cold weather routine.

Maddi is one such adventurer who excels at the art of the "winter getaway." We spoke with her about her latest journeys, the advantages of traveling south, and how to plan an unforgettable winter vacation. 

Where do you usually vacation during the winter and where do you typically travel from?

While living in Eugene, Oregon, I often traded the damp and dreary Pacific Northwest climate for sunnier destinations during my winter travels. I've visited places like Cabo San Lucas, Mexico, the Big Island and Maui in Hawaii, as well as some warm spots closer to home, such as San Diego and Los Angeles.

A few years ago, I relocated to New York City , and my first winter escape was to Cartagena, Colombia! Most of my winter adventures tend to happen at the end of February, as that’s when I start feeling a bit restless being cooped up inside [laughs].

How did you develop this winter travel tradition?

Some of my earliest trips were with my family. Hailing from Bend, Oregon, they frequently sought to escape the snow. With my brothers studying in different locations, my parents wanted to gather us all together and thought, why not go somewhere warm? Nowadays, I've simply continued this tradition after discovering how much I enjoy it!

What emotions do you experience upon arriving at a new, warmer destination?

Oh, stepping into a warm, humid environment after being in the cold and rain is such a blessing! From the very first moment in the sun, I feel an instant lift in my spirits. My favorite part is swapping my sneakers for flip-flops on that first day—Hawaii was especially a delightful surprise.

How do you feel when returning to winter at home?

Soaking up some vitamin D has always been beneficial. Each trip I’ve taken felt like a refreshing reboot, and I returned home energized to tackle school, work, or anything that came my way!

What were some of your favorite activities in each location?

In Hawaii, hiking was the main attraction. Maui features a breathtaking coastal drive known as “the road to Hana,” which leads to some amazing trails. One of these trails took us through a bamboo forest, where we had to lift our bags over our heads as we crossed a stream to reach a spectacular waterfall at the end!

Do you have any favorites from Cabo?

Absolutely! I really enjoyed snorkeling there. We also went on a glass-bottom boat tour around the iconic arches, which allowed us to gaze up at the rock formations while also peering down at the colorful tropical fish.

What has been your all-time favorite winter trip? 

Cartagena! It’s an amazing city to explore on foot, and I thoroughly enjoyed sampling the local cuisine—the ceviche is renowned worldwide, and the mojitos were incredibly refreshing in the warm weather.

Everyone I’ve shared my Cartagena experience with is eager to visit. You can meander through the vibrant streets, and with the lively Colombian atmosphere, there’s always something going on. It felt like there was live music on every corner every night! Plus, there’s an ancient fortress at the city's edge that was unlike anything I’d ever encountered.

It sounds like you’ve enjoyed many experiences that you wouldn’t have had at home.

Absolutely. Throughout winter, I tend to spend most of my time indoors. Being in nature is extremely important to me, which has been one of the greatest advantages of winter travel. 

Even in Los Angeles, it was a delightful experience to relax on the beach with a picnic, even if the weather wasn't warm enough for swimming.

What tips do you have for fellow travelers planning a winter getaway to escape the chill?

Be clear about what you want from your trip! I’m often attracted to destinations with lush greenery because that’s what I miss during winter at home. I also enjoy combining laid-back beach days with outdoor adventures.

While I do enjoy snow, my ideal getaway is somewhere warm, so I've learned to travel even further south than Southern California. Make a checklist and do some research to find a destination that perfectly suits your preferences!

So, where are you headed next?

I’m gearing up for a trip to Costa Rica for my next winter adventure—it has everything I’m looking for!