16 Incredible Winter Family Getaways — From Ski Adventures to Caribbean Retreats

Rovaniemi, Finland

Rovaniemi, the gateway to Finnish Lapland, is a true winter wonderland brimming with enchanting experiences — from reindeer sledding to breathtaking views of the northern lights. Families can relax in outdoor jacuzzis, take icy plunges, and enjoy saunas. For those seeking extra excitement, travel expert Carly Patane Moss from Black Tomato recommends a nighttime guided snowmobile adventure. After a day filled with Arctic fun, cozy up in a glass igloo amid the snowy landscape. 

Arenal, Costa Rica

Looking to swap the chill for an exhilarating family getaway in a warm, tropical paradise? The Arenal Volcano National Park area in Costa Rica is the heart of eco-adventure, perfect for tubing, canyoning, navigating hanging bridges, ziplining over lush canopies, and spotting local wildlife. “One of my absolute favorite spots for families in the area, Nayara Tented Camp, offers a rainforest retreat feel with glamping tents featuring wrap-around balconies and hammocks for relaxation, along with stunning views of the volcanic scenery,” says Moss. 

Park City, Utah

During ski season, Park City is an incredibly family-friendly destination thanks to its well-groomed runs and lessons from expert instructors. Beyond the slopes, guests can enjoy scenic gondola rides, dog sledding, and ice skating. Montage Deer Valley — a favorite resort among Dinogo readers — goes above and beyond for younger visitors with its Paintbox kids club, a tubing snow bowl, charming in-room camping setups, nightly s’mores, and even a bowling alley.

Bruges, Belgium

If you're looking for a destination brimming with charm and history for kids, Bruges certainly fits the bill with its winding canals, frost-kissed cobblestone streets, and medieval buildings. A stunning holiday locale featuring festive markets, the holiday spirit lingers well beyond December. “No matter your celebration, the city captures a joyful atmosphere that's hard to match,” notes Moss. With fewer crowds than during the summer, it's the ideal time for families to enjoy chocolate delights and partake in free historical walking tours.

Kaikōura, New Zealand

Sure, a trip to New Zealand involves many hours in the air. However, if your kids handle flying well and you're okay with adjusting to time zone changes, there's plenty for families to enjoy during winter (which is summer in the Southern Hemisphere). Moss suggests visiting Kaikōura, a coastal gem on the South Island famed for its wildlife. “Family-friendly activities include swimming with dolphins, whale-watching excursions, and birdwatching tours to spot majestic albatrosses and other seabirds in their natural environment.”

Toronto, Canada

Toronto remains a lively destination for families throughout the winter. Given the chilly weather, make sure to dress warmly for strolls along the waterfront, exploring the vibrant shops and eateries in the Distillery District, and sightseeing. Favorites for kids include Ripley's Aquarium of Canada and Casa Loma, one of the few castles in North America. When hunger hits, head over to St. Lawrence Market. Moss suggests visiting the charming Cabbagetown neighborhood for sledding followed by a cup of hot cocoa.

Maasai Mara National Reserve, Kenya

A safari offers an unforgettable adventure for both parents and kids. "Kenya's 'secret season' in winter presents a fantastic value for families compared to the busy Great Migration months, with fewer crowds, excellent weather, and plenty of wildlife sightings," notes Moss. Travelers of all ages will be thrilled by the opportunity to see lions, elephants, buffalo, rhinos, and a variety of birds at watering holes during daily game drives. The Maasai Mara National Reserve is also home to family-friendly lodges like Angama Mara. Pro tip: Kenya Air has direct flights from New York City to Nairobi.

Lake Geneva, Wisconsin

While summer attracts crowds to Lake Geneva, this Wisconsin gem is equally enchanting during the winter months. Just an hour's drive from Milwaukee, it's an ideal Midwest weekend getaway. Beyond its convenience, the array of activities for all ages and budget-friendly options truly captivate travelers, making it a perfect winter escape. With Winterfest—a free annual event featuring a spectacular snow sculpture competition—alongside ice skating, cross-country skiing, and snowmobiling, there's no shortage of frosty fun.

Siem Reap, Cambodia

After adjusting to the long flights, Siem Reap emerges as an excellent family vacation spot. It's home to the UNESCO World Heritage site of Angkor Wat, along with numerous other historic religious landmarks from the Khmer Empire. A morning spent temple hopping in a tuk-tuk provides children with insights into ancient history, while a stay at a resort like Zannier Hotels Phum Baitang, featuring a refreshing pool, offers the ideal retreat during warm afternoons before heading out to enjoy Phare, the Cambodian Circus or a classic Apsara dance performance.

Telluride, Colorado

A beloved destination for outdoor lovers, Colorado is famous for its mountain towns that thrive during winter. With exceptional skiing and snowboarding alongside plenty of après-ski activities, Telluride offers endless adventures for families visiting in the chilly months. “While some bustling spots in the Centennial State can be tricky to access, Telluride’s close proximity to various airports makes it one of the more accessible choices for winter sports — leading to easier flights and less time spent driving with kids,” notes Moss.

Antigua

With a multitude of stunning beaches featuring soft sands and crystal-clear waters, Antigua is designed to delight families of all shapes and sizes. “It offers amazing snorkeling opportunities around shallow coral reefs and Stingray City, along with off-shore scuba diving suitable for teens and older,” shares Moss. For those seeking adventure, helicopter tours provide breathtaking views of the rainforests and shimmering ocean. A hike to Shirley Heights, a historic military lookout, also rewards visitors with stunning panoramas. Family-friendly resorts include Curtain Bluff and Carlisle Bay.

London, United Kingdom

London ranks as one of the most family-friendly destinations in Europe. Melissa DaSilva, President of Trafalgar, reminds travelers that overcast skies and a bit of rain won’t dampen the winter fun. Grab tickets to a West End show, take a spin on the London Eye, and splash about in the numerous parks. “Harry Potter enthusiasts should definitely visit King’s Cross Station to capture a moment at Platform 9 ¾.” Traveling with little ones? The Carlton Tower Jumeirah offers special amenities for young guests, including tailored kids’ menus and family-friendly packages.

Orlando, Florida

Orlando may be a well-known choice for families, but its popularity is not a reason to overlook this fantastic destination. Yes, expect crowds at the various theme parks, especially during school vacations, but the excitement on kids’ faces as they zoom on roller coasters, snap photos with Mickey and friends, and enjoy unique Disney treats makes it all worthwhile. Additionally, skip-the-line passes and early entry options help minimize wait times, ensuring a magical experience for visitors of all ages. 

Grand Canyon National Park, Arizona

DaSilva encourages nature and adventure enthusiasts to consider a family getaway to Grand Canyon National Park during the tranquil off-season, when the crowds are thinner and the chances of capturing a perfect group photo are significantly improved. Although the North Rim is closed, the South Rim offers accessible hiking trails suitable for all skill levels and opportunities to observe wildlife, including elk and ravens. “It’s truly enchanting to take in the breathtaking sights of snow-dusted, banded rock formations and the valleys beneath from the scenic overlooks.”

Alentejo, Portugal

While Alentejo may not be the first place that comes to mind for winter travel, this rural gem in Portugal is an excellent destination for families looking to explore during the quieter months of December, January, and February. Families can enjoy cork tours, visit Badoca Safari Park, and even book a farm stay. Herdade da Malhadinha Nova, a Relais & Châteaux property on an active farm, features spacious accommodations, various animals like horses, cows, and pigs, and a renowned restaurant that provides coloring books and crayons for the little ones.

Reykjavik, Iceland

Reykjavik offers an easily accessible and budget-friendly flight from the East Coast of the United States, making it an exciting destination for families eager for action and adventure. This coastal capital is a cultural hub in Iceland, featuring the glass-domed Perlan interactive nature museum and the striking Hallgrimskirkja church, along with a variety of casual and upscale dining options. It also serves as a perfect base for day trips to attractions like Gullfoss Falls and the geothermal Blue Lagoon, as well as expeditions to chase the northern lights in more remote areas.