Gone are the days of being bored in the back seat whining, “Are we there yet?” Cross-generational travel is becoming more and more popular as those bored kids in the back seat grow up and want to enjoy time with their parents as adults. Vacations with parents, kids, grandparents, even great-grandparents give multiple generations a chance to spend quality time with each other, especially if they happen to live in different parts of the world. Face-to-face bonding time (and did we mention hugs?) just can’t be replicated via phone or Facetime. Convinced yet? Read on for the best destinations for cross-generational travel.


Level up beach vacations of the past and bring on the cross-generational bonding with a trip to Maui’s laid-back beaches, where everyone can take it easy with relaxing afternoons at the beach followed by shave ice. Take advantage of the many group discounts available and if you really want to go stress-free, consider booking an all-inclusive trip.


Napa-Sonoma isn’t just for wine lovers. A variety of critters from bees to bunnies live beyond the area’s many vineyards. Enjoy a day exploring Sonoma County Farm Trails, a network of local farmers, artisans, and producers around the area. Seek out petting areas and pony rides for the kids and the best locally made cheese (to pair with wine, of course) for the adults. Can’t resist spending a day at one of Napa-Sonoma’s wineries? Francis Ford Coppola Winery’s grounds are decked out with swimming pools designed with kids in mind. Book your chaise lounges in advance and you’ll be outfitted with everything you need, including a private shower and sparkling wine (for the over 21 crowd).

Hong Kong

The most important reason behind cross-generational travel is that irreplaceable quality time we keep going on about. When it’s just not possible to ship everyone off to a new destination, go visit the older generations of the family. The beauty of this type of cross-generational travel is that younger generations will be able to learn about their family’s cultures first hand. Even if your family’s roots don’t touch down in Hong Kong, Hong Kong Disneyland and Ocean Park theme parks and the Peak tram are three very solid reasons for anyone to visit. The joy of discovering a new place together is a pretty special experience, too.


Disney World is a family classic that never gets old or goes out of style. Whether it’s your first visit or your fiftieth, make family memories together “where dreams come true” in Orlando. Our advice? Do what it takes to keep the visit as stress-free as possible. Buy the FastPass sitting in your online cart, plan a loose itinerary, and have realistic expectations for what you can see and do and you’ll leave with nothing but priceless family memories.

Cabo San Lucas

The non-stop fun and sun of Cabo San Lucas is a vacation mantra everyone can get behind. Sign the whole family up for surf lessons or a kayaking trip. Cabo has had a reputation for being a spring break destination in the past, but these days the co-ed crowd has become a more family-friendly crew headed to Cabo for adventure. Be aware: Not all of Cabo’s beaches are swimmable due to strong currents. Be sure to book a hotel on a kid-friendly beach or with its own pool, so you don’t have to sacrifice beach time for safety.


It’s hard to find time to gather around the table over a delicious meal most days. In Rome, you won’t have that problem. The fresh simplicity of Roman cuisine will have you gathering around the table again and again, giving your family time to relax and just enjoy each other’s company. Who knows? Maybe you’ll return home with a new tradition. Sunday family dinner, anyone?


This quintessential summer escape conjures up images of ice cream, lazy days spent at the beach or on a sailboat, and relaxed meals of wine and fresh seafood. Planning a Nantucket getaway is great if you’d rather stay in one place spending time with extended family taking in the picturesque views.


Paris has the ability to spark magic in the young, the old, and everyone in between. Enjoy the pleasure of whiling away an hour or two at a sidewalk café, discover the winding streets and colourful artists of Montmartre, and enjoy Paris’ famous parks and plentiful playgrounds together. Jardin du Luxembourg is a favourite among families thanks to plentiful activities. Choose from pony rides, puppet shows, sailboats, and a carousel, or better, experience it all.

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