Winter Family Travel Guide: Awesome Destinations In America & Beyond

Stowe Mountain Resort, VT

Got the travel bug? Here’s our wanderlustful winter destination guide to suit every family’s interests (and climate preferences). For resort-loving fams, don’t forget to also check out New York Family editor Eric Messinger’s personal picks to learn all about his family’s fave warm and cold weather options.


Where Ice Cream & Snow Adventures Meet
Stowe, VT
This artsy, hip New England city is blanketed with beautiful bright snow during the winter. But just because it’s cold doesn’t mean a visit to the Ben & Jerry’s Factory isn’t still in order. Kids under 12 enter for free to enjoy the tour and tastings. For legendary ice skating, snowshoeing, and shelter building fun, check out Appletree Learning Center. And, parents, don’t forget to sample one of the area’s fine microbrews while your kids enjoy steaming mugs of cocoa and marshmallows.

The Ultimate Snowbound Escape
Vancouver, Canada
Vancouver is not just about the slopes, though there’s plenty of terrain to satisfy both novice and veteran skiers in western Canada—not to mention sled rides and rinks perfect for backward ice skating. Off the runs, Vancouver’s toy store mecca, Kids Market Granville Island, features good eats, cool clothing, and unique crafts. Warm up with a hot chocolate and pastry from Bleu Door Bakery before taking in one of the city’s six kid-friendly (and adult-worthy) museums.

A Not-Too-Far-From-Home Respite
Saugerties, NY
For a destination easily reached by car, Saugerties in upstate NY makes an idyllic escape from the city. Stay at the family-friendly Smythe House B&B, where owners Justine and David cook a mouth-watering breakfast of each family member’s choosing. In town, indulge in some quiet time at the Inquiring Minds Bookstore, then fuel up at reputable restaurants like Miss Lucy’s Kitchen for seasonal dishes and must-have desserts (plus a separate kids’ menu), Slices for gourmet pizza (delicious even by tough NYC standards!), and the Main Street Restaurant for comfort classics.


A Nature & Wildlife Haven
Montego Bay, Jamaica
Families are more than welcome in Jamaica, where the number of kid-friendly hotels is growing at a rapid pace. Choose from the all-inclusive Half Moon, where kids under 16 eat and sleep for free, or Beaches Negril Resort and Spa, where there’s a club, buffet, and entertainment exclusive for kids. Of course, a slew of cool activities also await off-site—YS Falls boasts cascading waterfalls, wading pools with underground springs, and tube rides, while Island Route Swamp Safari will make a birdwatcher out of someone in your family.

The Beach Vacation Of Family Dreams
When the chill bites in the city, better head south where the breeze is moderate and accompanied by the slick sweet smell of ocean saltwater. In Bermuda, lounge on the beach and dive in water sports, then join one of the daily Crystal Cave tours for a sparkling adventure. Animal lovers will find endless delight at the Aquarium/Museum/Zoo, a gargantuan complex with more than 200 species of fish and 300 species of mammals, birds, and reptiles. Stay at the Pompano Beach Club for more pool fun and water activities galore.

Fantasy Crystal Cave in Bermuda; photo by Craig Stanfill

Florida’s Exotic Getaway
Key West, FL
In Key West, a calmer alternative to busy Orlando, not only will your family eat well—think fresh fish, Cuban fare, key lime pie, and ice cream galore—but you’ll also keep busy with a flurry of under-the-radar activities. From snorkeling at the Nature Preserve and Marine Park to getting active at the Astro City Playground before a full day of testing the waves at Higgs Beach, no one will ever complain of boredom. (Psst—Hyatt Key West is an excellent accommodation for families.)


Filling Up On Food & History
Montreal, Canada
It’s easy for visitors to get caught up in Montreal’s diverse food offerings, from poutine to smoked meats, but adventure-seeking and history-loving fams have plenty to do, too. Work off your meals at the Allez Up indoor sports facility, where even beginners can get a taste of rock climbing. Transport yourself to an era past along Old Montreal’s cobblestones, then find shelter from the cold at the part museum, part zoo Biodome. Bonus: Quebec City’s famed Winter Carnival—full of snow baths, ice slides, larger-than-life foosball, and more—makes for a great day trip in the first two weeks of February.

Mole & Magnificent Ruins
Oaxaca, Mexico
Oaxaca, a far cry from the rowdy Cancun of spring break lore, is an excellent option for a family vacation with culture and creativity south of the border. Enjoy a mole lunch at the city’s main market and taste Oaxaca’s famed chocolate in raw or beverage form. Archaeological sites like Monte Alban, Mitla, and Lambityeco imbue families with a feel for the city’s immense history, and for ultimate immersion, stay at a unique bed and breakfast, like the Casa de las Bugambilias, serving up authentic Oaxacan breakfasts complete with fresh juice and buttery pastries.

In Great Southwest
Tucson, AZ
It’s all about fun with a dose of learning in Tuscon. Get started with horseback riding, cave tours, and picnicking in the historic district of Colossal Cave Mountain Park, then hit up the Arizona-Sonora Desert Museum for unbeatable desert animal sightings. For the best way to experience Tucson’s natural beauty, rent bikes for the whole family. The city is known for it’s Mexican cuisine; get a taste at Sir Veza’s Taco Garage, which makes more than twenty taco varieties.


Making chocolate in Oaxaca, Mexico; photo by Janet Lackey

Family-Friendly Partying
Circus Circus, NV
Think Vegas is only for high-rollers and all-night partiers? Think again. There’s room for the whole family at the Circus Circus resort, which houses an amusement park encompassing a new backward-launching coaster coming this December, bumper car track, 4D theater, and Ferris wheel. Every half hour also brings live circus acts with jugglers, trapeze artists, and acrobats, not to mention Pride Family Bingo on Wednesdays. Should you choose to venture offsite, the Las Vegas Springs Preserve boast a number of museums, garden workshops, train rides, and bike rentals.

Roller Coasters With A Side Of Pie
Knott’s Berry Farm, CA
Perhaps Disney (Land and World) will always produce nostalgic memories, but for a unique alternative, try Knott’s Berry Farm, a 160-acre Snoopy-themed amusement park. At this former berry farm, you can treat the family to the park’s famous boysenberry pie after you finish off a yummy chicken dinner. But first, hop on the wooden Ghost Rider for a classic rickety ride, Woodstock’s Airmail for a pint-sized vertical plunge, and the Timber Mountain log ride for a modest splash.


An Exotic Mash-Up Of Urban Living & Beach Bumming
Yes, it’s far away, but Thailand is an unparalleled cultural experience for families who love to really get away. Spend a night or two getting acquainted in dizzying Bangkok, brimming with street vendors selling staples like betel leaf wraps and Thai tea. Take a day to explore the landmarks and ruins that make up the Ancient City, then retire to the coast—but not without first indulging in a tuk-tuk rickshaw ride. Once beachside, delight in hidden waterfalls, coconut ice cream, and, at night, a sky full of stars. Hospitable accommodations abound (we like the Buri Rasa on Koh-Phangan), and their local staff can help arrange a kayak ride or even charter a speedboat for the family.