Destinations, Family Travel, Travel Inspiration, Travel Planning

February 28, 2025

Where to Go for Winter Break

Yes, the spring buds are just barely coming into bloom on the trees—but it’s already time to think about your winter travels. If you want to make the most of your kids’ winter break from school, it pays to start planning soon. Jumpstarting the planning process now means you’ll be able to take advantage of the best flight availability, and the widest range of accommodation options.

The only question is: where to go? I’ve put together some family-friendly destination ideas for you, depending on what kind of escape your family is craving once the temperatures drop.

If you want to embrace the cold weather

There’s something simply magical about snow—so if your family wants to make the most of this special season, then nothing beats a ski trip! As a bonus, there are many amazing ski spots in the U.S., so you don’t have to spend your precious winter break time flying somewhere international. For family-friendly skiing, I’d recommend:

Steamboat Springs, Colorado

Steamboat Springs is ringed by several mountain peaks, which means your family has lots of choices for digging into some pristine powder. If you all are beginner skiers, you can easily stick to gentle slopes that match your skill level. If you’re practically old pros, there’s plenty of more challenging runs to keep you entertained. The town of Steamboat Springs itself is charming to explore, and your family can also enjoy a soak in mineral hot springs, soaring gondola rides, and ice skating.

Deer Valley, Utah

This Park City skiing hotspot is very welcoming to families. You’ll find plenty of shorter, beginner-friendly slopes to try, plus an award-winning ski school for lessons. The slopes are meticulously groomed and the atmosphere is elegant yet welcoming. This is the spot to come for a more upscale, seamless ski experience for the family.

If you want to escape the cold weather

You and your family view winter break as an opportunity to take a break from the cold. So, where should warm weather fans escape to? Here are two ideas:

Costa Rica

The land of pura vida is an excellent choice for families who want to stay active on vacation, while staying warm. December is Costa Rica’s dry season, so it’s a great time of year to visit. Explore wildlife-rich jungles where you can spot sloths and monkeys, take surfing lessons on Costa Rica’s golden coastline, hike around volcanoes, or zipline through the treetops for incredible aerial views. Because of all of the activity options, I would recommend Costa Rica as a perfect destination for families with older children.

The Bahamas

If all you truly want to do during winter break is get away from it all with your family, the Bahamas is a top choice. It’s an easy-to-get-to Caribbean destination, and its proximity to the U.S.—the islands lay not far off the coast of Florida—means you won’t have to endure a long plane ride before you can start your vacation. The Bahamas are known for powdery white-sand beaches and shallow turquoise waters, making it an ideal island escape for families with young children. There are a number of family-friendly resort options that will ensure your stay is safe and seamless.

Ready to start planning your family’s winter break escape? I’d love to help—you can learn more about my travel design services right here, or complete your trip inquiry form now to get started!

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