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

From ski destinations in Finland to safaris in Kenya, here are 16 of the best winter family vacation ideas, according to travel experts.

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By Lindsay Cohn Published on Oct 29, 2023, 10:00 AM

16 Best Winter Family Vacations — From Ski Trips To Caribbean Escapes
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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 to the Costa Rican jungle and the Caribbean island of Antigua, while avid skiers will love the 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 destinations for the best winter family vacations

Rovaniemi, Finland

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The gateway to Finnish Lapland, Rovaniemi is a real-life winter wonderland full of magical moments — from reindeer sledging 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.

Book your stay at HAAWE Boutique Apart Hotel via Booking.com

Book your stay at HAAWE Boutique Apart Hotel via Agoda.com

Arenal, Costa Rica

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Ready to trade the cold for an action-packed family holiday somewhere warm and tropical? The epicentre 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 favourite 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.

Book your stay at The Springs Resort & Spa at Arenal via Booking.com

Book your stay at The Springs Resort & Spa at Arenal via Agoda.com

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Park City, Utah

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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 sledging, and ice skating.  Montage Deer Valley — one of Travel + Leisure readers’ favourite 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.

Book your stay at Montage Deer Valley via Booking.com

Book your stay at Montage Deer Valley via Agoda.com

Bruges, Belgium

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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 option for winter family vacations 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.

Book your stay at Dukes' Palace Brugge via Booking.com

Book your stay at Hotel Dukes' Palace Brugge via Agoda.com

Kaikōura, New Zealand

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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.”

Book your stay at Hapuku Lodge & Tree Houses via Booking.com

Book your stay at Hapuku Lodge and Tree Houses via Agoda.com

Toronto, Canada

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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 favourites for little ones. When hunger strikes, head to St. Lawrence Market. Moss recommends venturing to the quaint neighbourhood of Cabbagetown for sledging followed by hot cocoa.

Book your stay at The Ritz-Carlton, Toronto via Booking.com

Book your stay at The Ritz-Carlton, Toronto via Agoda.com

Maasai Mara National Reserve, Kenya

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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. Travellers 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.

Book your stay at Fairmont Mara Safari Club via Booking.com

Book your stay at Fairmont Mara Safari Club via Agoda.com

Lake Geneva, Wisconsin

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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 travellers 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.

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Siem Reap, Cambodia

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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.

Book your stay at Zannier Hotels Phum Baitang via Booking.com

Book your stay at Zannier Hotels Phum Baitang via Agoda.com

Telluride, Colorado

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A favourite 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 travelling 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.

Book your stay at The Hotel Telluride via Booking.com

Book your stay at The Hotel Telluride via Agoda.com

Antigua

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Home to countless beautiful beaches with soft sand and clear water, Antigua aims to please families of all sizes. “It supplies incredible snorkelling 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.

Book your stay at Carlisle Bay via Booking.com

Book your stay at Carlisle Bay via Agoda.com

London, United Kingdom

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London is one of the most family-friendly cities in Europe. Melissa DaSilva, President of Trafalgar, reminds travellers 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.

Book your stay at The Carlton Tower Jumeirah via Booking.com

Book your stay at The Carlton Tower - Jumeirah via Agoda.com

Orlando, Florida

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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.

Book your stay at The Ritz-Carlton Orlando, Grande Lakes via Booking.com

Book your stay at The Ritz-Carlton Orlando, Grande Lakes via Agoda.com

Grand Canyon National Park, Arizona

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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 mesmerising to soak in the spectacular views of snow-covered banded rock formations and the valleys below from scenic lookouts.”

Book your stay at Squire Resort at the Grand Canyon, BW Signature Collection via Booking.com

Book your stay at Squire Resort at the Grand Canyon, BW Signature Collection via Agoda.com

Alentejo, Portugal

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Alentejo might not be the first spot to spring to mind as a winter destination for a family vacation, 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 colouring books and pencils for kiddos.

Book your stay at Herdade da Malhadinha Nova - Relais & Châteaux via Booking.com

Book your stay at Herdade da Malhadinha Nova - Relais & Chateaux via Agoda.com

Reykjavik, Iceland

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Reykjavik is an awesome city for a  family vacation 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.

Book your stay at The Reykjavik EDITION via Booking.com

Book your stay at The Reykjavik EDITION via Agoda.com

(Hero and feature image credit: Jedamus_Lichtbilder/Getty Images)

This story first appeared on travelandleisure.com

Related: Bookmark This: 20 Ideas For A Wholesome Family Vacation

Written By

Lindsay Cohn

Lindsay Cohn

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