16 Best Winter Family Vacations — From Ski Trips to Caribbean Escapes

Here are 16 of the best winter family vacation ideas, according to travel experts.

Family vacations are a great way to bond and create shared memories to last a lifetime, and winter provides ample opportunities to get away between holiday breaks from school and long weekends. Whether you’re trying to score a deal or ready to splurge, there are plenty of destinations that bring the fun — it’s just about picking the right place to suit your vacation interests and goals. Sun worshipers should look at flights down to the Costa Rican jungle and the Caribbean island of Antigua, while avid skiers will love the domestic slopeside hotspots of Park City and Telluride. Parents keen to experience a city break with kids in tow might want to jet off to Toronto. If it works within your schedule (and maybe you have a few extra frequent flier miles to spare), it’s worth considering a long-distance trip somewhere fascinating like Siem Reap.

Here are 16 of the best winter family vacation ideas, according to travel experts.

Related: 22 Best Family Vacations in the U.S. That Are Perfect for Everyone — From Toddlers to Teens

Rovaniemi, Finland

The gateway to Finnish Lapland, Rovaniemi is a real-life winter wonderland full of magical moments — from reindeer sledding to surreal views of the northern lights. Outdoor jacuzzis, ice plunges, and saunas are waiting for parents and older kids to unwind. For families looking for even more thrills, Carly Patane Moss, travel expert at Black Tomato, suggests booking a nighttime guided snowmobile excursion. At the end of a day full of Arctic adventures, curl up in a glass igloo surrounded by snowy terrain.

Arenal, Costa Rica

Ready to trade the cold for an action-packed family holiday somewhere warm and tropical? The epicenter of eco-adventure in Costa Rica, the area surrounding Arenal Volcano National Park is ideal for tubing, canyoning, traversing networks of hanging bridges, ziplining over forest canopies, and peeping native wildlife. “One of my absolute favorite spots for families to stay in the area, Nayara Tented Camp gives off rainforest hideaway vibes with glamping tents that have wrap-around balconies with hammocks for chilling out and sweeping views of the volcanic landscape,” says Moss.

Park City, Utah

Park City is an exceedingly family-friendly destination during ski season thanks to groomed runs and lessons with skilled instructors. Besides hitting the slopes, visitors can look forward to scenic gondola rides, dog sledding, and ice skating.  Montage Deer Valley — one of Travel + Leisure readers' favorite resorts in Utah — goes all out for younger guests with the Paintbox kids club, a snow bowl for tubing, an adorable in-room camping amenity, nightly s’mores, and a bowling alley.

Bruges, Belgium

If you’re searching for a place that’s chock-full of charm and brings history to life for kiddos, Bruges definitely ticks the boxes with its meandering canals, flake-frosted cobbled streets, and medieval architecture. A dazzling holiday destination with yuletide markets, the spirit of the season extends well past the end of December. “Regardless of what you celebrate, the city evokes that festive feeling that’s hard to replicate,” notes Moss. Without the crowds of the summer months, it’s the perfect time for families to indulge in chocolate treats and join free history walking tours.

Kaikōura, New Zealand

Admittedly, a trip to New Zealand requires a lot of hours up in the air. But if your kids are pretty good fliers and you don’t mind dealing with time zone differences, it has a ton for families in the winter (the summer in the Southern Hemisphere). Moss recommends Kaikōura, a coastal town on the South Island that’s beloved for wildlife encounters. “Family-friendly experiences range from swimming with dolphins to whale-watching boat rides to birdwatching tours to see majestic albatross and other sea birds in their natural habitat.”

Toronto, Canada

Toronto still buzzes with things for families to see and do all winter long. Since it’s quite cold, just remember to pack accordingly to keep everyone nice and toasty for walks along the waterfront, exploring the shops and restaurants in the vibrant Distillery District, and sightseeing. Ripley's Aquarium of Canada and Casa Loma, one of a handful of castles in North America, are favorites for little ones. When hunger strikes, head to St. Lawrence Market. Moss recommends venturing to the quaint neighborhood of Cabbagetown for sledding followed by hot cocoa.

Maasai Mara National Reserve, Kenya

A safari is a once-in-a-lifetime trip for parents and kids. “Kenya’s ‘secret season’ in the winter offers a terrific value for families as compared to the Great Migration months, coupled with fewer visitors, terrific weather, and ample animal sighting,” says Moss. Travelers of all ages will go wild for the chance to spot lions, elephants, buffalos, rhinos, and various species of birds at the watering holes on daily game drives. Maasai Mara National Reserve also brims with family-friendly lodges such as Angama Mara. Pro tip: Kenya Air operates direct flights between New York City and Nairobi.

Lake Geneva, Wisconsin

Summer draws the crowds to Lake Geneva, but this Wisconsin town wows families in the cold months, too. Located just an hour from Milwaukee, it’s a quick and easy Midwest weekend getaway. Convenience aside, the spate of activities for all ages and affordable rates really win over travelers and make the town a great place to escape in the winter. Between Winterfest — the free annual event with a larger-than-life snow sculpture competition.— ice skating, cross-country skiing, and snowmobiling, it overflows with frosty fun.

Siem Reap, Cambodia

Once you get over the long-haul flights, Siem Reap makes a lot of sense as a family vacation destination. It’s home to UNESCO-listed Angkor Wat as well as dozens of other ancient religious sites that date back to the Khmer Empire. A morning of temple hopping via tuk-tuk teaches kiddos about the distant past, and staying at a resort like Zannier Hotels Phum Baitang with a sparkling pool means having the perfect place to cool down in the balmy afternoons before going to watch Phare, the Cambodian Circus or a traditional Apsara dance performance.

Telluride, Colorado

A favorite of outdoor enthusiasts, Colorado is well-known for its mountain towns that come alive in the winter. From top-notch skiing and snowboarding to abundant après activities, there’s certainly no shortage of adventure for families traveling to Telluride during the frosty season. “Though a pain point for some buzzy places in the Centennial State, Telluride’s proximity to multiple airports makes it one of the more accessible options for winter sports — which means more convenient flights and less time driving in the car with kids,” says Moss.

Antigua

Home to countless beautiful beaches with soft sand and clear water, Antigua aims to please families of all sizes. “It supplies incredible snorkeling around shallow coral reefs and Stingray City as well as off-shore scuba diving for teens and older,” says Moss. More on the adventure front, helicopter tours give passengers a birds-eye view of the rainforests and sparkling ocean. A trek to Shirley Heights, a former military lookout, also delivers some superb vistas. Kid-friendly resorts include Curtain Bluff and Carlisle Bay.

London, United Kingdom

London is one of the most family-friendly cities in Europe. Melissa DaSilva, President of Trafalgar, reminds travelers that cloudy skies and some mild rain won't stop the fun in the winter. Snag tickets to a West End play, ride the London Eye, and slosh around in the many parks. “Harry Potter fans should stop by King’s Cross Station and snap a photo at Platform 9 ¾.” Traveling with tots? The Carlton Tower Jumeirah caters to the youngest guests with curated kids’ menus and family-friendly packages.

Orlando, Florida

Orlando may be an obvious pick for families, but notoriety isn’t a reason to look past somewhere wonderful. Yes, there will be crowds at the various theme parks — especially during school holidays — however, it’s worth contending with queues to watch the joy on kids’ faces while they’re zipping around coasters, posing alongside Mickey and his pals, and scarfing down tasty, only-in-Disney treats. Plus, skip-the-line passes and early entry options do help cut down on the wait times, making it a magical trip for visitors of all generations.

Related: 23 Best Things to Do in Orlando With Kids — From Theme Parks to Nature Experiences

Grand Canyon National Park, Arizona

DaSilva encourages nature and adventure lovers to plan a family vacation to Grand Canyon National Park during the peaceful off-season when it’s far less busy and your chances of snapping a frame-worthy group photo are way higher. While the North Rim remains closed, the South Rim is open with hiking trails for all skill levels and the chance to spot wildlife, from elk to ravens. “It’s particularly mesmerizing to soak in the spectacular views of snow-covered banded rock formations and the valleys below from scenic lookouts.”

Alentejo, Portugal

Alentejo might not be the first spot to spring to mind as a winter destination, but that doesn’t mean Portugal’s agrarian heartland isn’t a great place to travel with the whole crew during the quiet months of December, January, and February. Families can do cork tours, visit Badoca Safari Park, and book a farm stay. Herdade da Malhadinha Nova, a Relais & Châteaux property on a working farm, has spacious accommodations, animals — horses, cows, and pigs — and an acclaimed restaurant with a stash of coloring books and pencils for kiddos. 

Reykjavik, Iceland

An easy, affordable flight from the East Coast of the United States, Reykjavik is an awesome city for families that puts action and adventure within reach. The coastal capital is a hub of Icelandic culture that’s home to the glass-domed Perlan interactive nature museum and the concrete Hallgrimskirkja church as well as casual and fine-dining restaurants. It’s also a great jumping-off point for day trips to Gullfoss Falls and the geothermal Blue Lagoon as well as northern lights-chasing expeditions in more far-flung corners.

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