Maui coastline

Sometimes it’s just more fun when everyone’s there. Family travel not only creates lasting memories, but it also offers the kind of flexibility that lets everyone have a great trip. When mom and dad need some alone time, grandma and grandpa can step in. And when little ones are having fun at a kids’ club, the grown-ups can bond over shared passions such as golf, museum- and gallery-hopping, or dining on local cuisine. Here are 10 places in the U.S., Canada, Mexico, and Caribbean that the whole group will love.


Why it’s perfect: It’s hard to beat Maui for sunny weather, family-friendly resorts, and activities for all ages. “The Magic Isle” has lots of tricks up its sleeve — from some of Hawaii’s best beaches and golf courses to back-to-nature adventure, farm-to-table dining, and fun foods (colorful shave ice, Portuguese malasada doughnuts, and sweet tropical fruits) that kids love.

For kids: Dolphin and whale-watching tours, hiking volcanic Mt. Haleakala, outrigger canoe and Atlantis submarine rides, surf school, hula lessons, and snorkeling galore.

For grown-ups: Golf (on 10 courses), scenic drives (through Upcountry and the Road to Hana), scuba diving, sunset catamaran cruises, fine dining on Hawaiian regional cuisine, and stress-zapping spa treatments.

Helpful tip: You don’t have to fly via Honolulu; there are non-stops to Maui from more than a dozen cities, including Los Angeles, San Francisco, Salt Lake City, Chicago, Denver, Dallas, and Phoenix.

Montreal and Québec

Why it’s perfect: French-speaking Montreal and Québec City, located about 2.5 hours apart by car, are close to home but feel far away (and are a bargain at current exchange rates). While Montreal blends old and new, Québec City celebrates its 410-year history with tons of charm. Both offer activities for all ages that evolve with the seasons — festivals in summer, foliage in fall, ice carnivals in winter, and maple syrup season in spring. Say, “Oui!” to fun.

For kids: The Montreal Science Center, La Ronde amusement park, Montreal Zipline, the Aquarium du Québec, iSaute trampoline center, and Winter Carnival — plus the favorite local fast food: poutine (French fries with gravy and cheese).  

For grown-ups: Summer-long music and comedy festivals, Montreal Museum of Fine Arts, Montreal Botanical Gardens and galleries, shops, and excellent dining in both cities.

Helpful tip: If your kids don’t have passports you can still go: Children under age 16 can travel to Canada with a birth certificate.

Washington, D.C.

Why it’s perfect: From the free stuff — museums, famous monuments, and a zoo — to the innovative dining scene that’s emerged over the past decade, our nation’s capital and its neighboring cities offer so much to see and do it’s almost impossible to enjoy everything in a single trip. Visit during cherry blossom season (early April) for a visual treat.

For kids: All the Smithsonian Museums (American History, Natural History, and Air & Space) are especially fun, the National Zoo (home to three giant pandas), the International Spy Museum (ideal for junior sleuths), the U.S. Mint (see real money being made), the White House (advance reservations required for a tour), and, of course, the Lincoln Memorial.

For grown-ups: All the stuff kids love you will, too — plus visit the National Gallery and the National Museum of African American History & Culture, and stroll around the Tidal Basin.

Helpful tip: If you love the charm of Georgetown, try neighboring Alexandria, VA (15 minutes by Metro), where historic 18th- and 19th-century architecture, a seasonal waterfront beer garden, and the free National Inventors Hall of Fame offer fun for all ages.  

Alaska Cruise

Why it’s perfect: Cruises are ideal for family travel because they’re convenient (many sail round-trip from Seattle or Vancouver) and offer great value. But what makes an Alaska cruise, available from late May to mid-September, especially appealing is that it allows all ages to easily see some of Mother Nature’s most remote wonders — from glaciers to grizzly bears. Plus, there’s tons of fun onboard our favorite ships cruising Alaska.

For kids: Excursions include zip-lining, dogsledding (and meeting adorable husky puppies), hiking, wilderness safaris, whale watching, and eagle and grizzly spotting, while onboard activities vary by ship but include kids’ clubs, pools and waterslides, movies, and arcades.

For grown-ups: While ashore there’s salmon fishing, kayaking or snorkeling adventures, scenic train rides, gallery tours, and shopping; onboard many ships offer musical and Broadway-style entertainment, wine tasting, spa treatments, and cooking or mixology classes.

Helpful tips: Alaska cruises are very popular so book six to nine months out. For the best deals, sign up for alerts from several cruise lines and watch for a sale.


Why it’s perfect: It’s inevitable: Your kids will harass you until you take them to this place where theme parks collide — so why not make it a “the more, the merrier” vacation? Whether your little ones are Disney Princess or Harry Potter wannabes, they’ll be entranced by Orlando’s make-believe magic. And if you believe, you’ll have a blast, too. Plus, the nearby Kennedy Space Center educates and delights all ages.

For kids: Between Disney’s four parks (Magic Kingdom, Animal Kingdom, Hollywood Studios, and Epcot), Universal Studios and Universal Islands of Adventure (home to the Wizarding World of Harry Potter), and SeaWorld, there’s just too much fun to count.

For grown-ups: Explore charming Winter Park, home to the Morse Museum (with its astounding Tiffany glass collection) and local restaurants, wine bars, and brew pubs. Outlet shopping is plentiful in Orlando, too.

Helpful tips: As appealing as on-site Disney or Universal resorts might seem, you may find better value in a condo-style resort (some offer free shuttles to nearby parks), which allows for affordable meal prep and downtime. Also, given exorbitant park ticket prices, check out deals on multi-day passes (buy ahead online to save) and read up on time-saving tips (such as FastPass at Disney).  


Why it’s perfect: Soft white sand, endless sun, and calm turquoise water by day and the ka-ching of casinos by night (many resorts have them on property) make this arid Dutch island in the Southern Caribbean a favorite. Plus, all-inclusive resorts as well as walkable dining options along Palm Beach make Aruba an easy, breezy escape.

For kids: Pools galore (many with fun slides and waterfalls), off-road Jeep tours, visits to a butterfly or ostrich farm or a donkey sanctuary, and stand-up paddleboard lessons.

For grown-ups: Scenic off-road adventures, golfing, gaming (casinos open at noon), wreck diving, deep-sea fishing, wind and kite surfing, Segway tours, spa visits, and duty-free shopping in the colorful capital, Oranjestad.

Helpful tips: Aruba’s location below the hurricane belt makes June to October (Atlantic hurricane season, also low season in the Caribbean), a great time to vacation here and save.

California's Northern and Central Coast

Why it’s perfect: Road trip, anyone? From San Francisco to Monterey Bay to Hearst Castle, there are plenty of attractions and activities for the entire family. With big city culture and scenic Pacific coast panoramas, this journey has something for everyone.

For kids: The ups and downs of San Francisco’s legendary cable cars, the sea lions and seafood treats of Pier 39 and Fisherman’s Wharf, the prison cells of Alcatraz, and the cool exhibits of the Exploratorium, the Walt Disney Family Museum, and the California Academy of Sciences. Further south, there’s the amusement pier in Santa Cruz and the Monterey Bay Aquarium.

For grown-ups: Walk across the Golden Gate Bridge or a stroll through the Palace of Fine Arts or Ferry Building Marketplace (all free) — plus an amazing restaurant scene. Along the coast, golfing at Pebble Beach (or at least the 17-mile scenic drive), the retro-glam architecture of Hearst Castle in San Simeon and wining, dining, and gallery-hopping in Carmel.

Helpful tips: Ride the Powell-Hyde cable car downhill from Union Square for the biggest thrill, book popular Alcatraz visits in advance, and enjoy a family-style dim sum meal in Chinatown.

Jackson Hole

Why it’s perfect: Old West ambience meets amazing wildlife at the gateway to both Yellowstone and Grand Teton national parks. Jackson Hole, with its outdoor-adventure vibe, is a place that’s not only postcard-perfect, but also offers cool things most kids (and kids at heart) don’t typically get to do.  

For kids: Yellowstone, America’s oldest national park, has geysers galore, along with wildlife safaris and eco adventures to spot herds of buffalo, resident bears, and elk. Other activities: action-packed dude ranches and covered-wagon cookouts.

For grown-ups: Fly fishing, horseback riding, soaking in the thermal waters of Granite Hot Springs, sipping whiskey at a craft distillery (or cabernet at a winery or beer at a brewery) or visiting the National Museum of Wildlife Art.

Helpful tips: Summer and winter are peak seasons (with correspondingly high hotel rates), so consider a visit in late May or early September if school schedules allow.

Riviera Maya, Mexico

Why it’s perfect: Affordable and easy to get to, this coast south of Cancún is lined with family-friendly all-inclusive resorts and authentic Mayan cultural sites (including Tulum, Coba, and Chichen Itza) that will spark the imaginations of budding archeologists. You’ll soak up the Caribbean sun while enjoying eco-adventure.

For kids: Swimming and snorkeling at resorts or at Mayan-themed aqua parks (Xcaret or Xel-Ha), kids’ club activities that range from scavenger hunts to handicrafts classes, zip-line adventures, and excursions to Mayan ruins.

For grown-ups: Watersports (from diving to kiteboarding), cave swimming in grotto-like cenotes, discovering flavorful of Yucatecan cuisine, and shopping Fifth Ave. in Playa del Carmen.

Helpful tips: For the best value, consider a visit right after Thanksgiving or during the first two weeks of December, when room rates are still low.


Why it’s perfect: History charms and entertains in this distinctively American city with its walkable neighborhoods and fun-yet-educational attractions. Boston also offers easy access to other top Massachusetts destinations, including the beaches of Cape Cod, the historic settlement at Plymouth, and the historically witchy Salem.

For kids: The Freedom Trail (where the American Revolution comes alive at Paul Revere’s house, the Old North Church, and more), the USS Constitution (America’s oldest commissioned warship), the New England Aquarium (to ogle thousands of colorful inhabitants), and 106-year-old Fenway Park (home of the Red Sox from April to September).

For grown-ups: The Museum of Fine Arts and Institute of Contemporary Art, the John F Kennedy Presidential Library and Museum, and the food scene (from fresh seafood to contemporary offerings from some of New England’s top chefs).

Helpful tips: Early May and late September tend to be ideal for a visit — comfortable weather, fewer crowds, and good hotel rates.

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