Multigenerational Travel: A Q&A with Chris Chesak

Chris Chesak is the executive director of the Family Travel Association, a new coalition that aims to simplify the sometimes dizzying complexities of planning a family trip, among other goals. Chesak has more than two decades of experience in the travel industry, including stints with the Adventure Travel Trade Association, the American Hiking Society and the American Alpine Club. As the father of two school-age daughters, he has now turned his career to focus on family vacations.

IndependentTraveler.com: Many grandparents talk of wanting to spend their money with their grandchildren, rather than leaving it all to them. Is this a trend you are seeing?

Chris Chesak: There is an overall trend within our population of people starting to shift their vision of personal wealth away from the acquisition of inanimate things to more experience-based wealth. Instead of purchasing more and more “stuff,” people are valuing experiences. And as older generations are entering the wealth distribution phase of their lives, they are using their wealth to facilitate creation of deep, lasting memories rather than just a larger pile of money to leave to the kids when the grandparents pass on.

IT: Have you ever traveled with grandparents?

CC: Just this summer I had the amazing opportunity to travel to China with my wife, 8- and 10-year-old daughters, and mother-in-law. What an incredible thrill to stand on the Great Wall of China. But standing on that icon with your kids and their grandmother? Absolutely amazing! And while we were able to take a gondola to about mid-mountain, we still had to then climb 299 steps to get to the wall itself. What a great achievement for our little girls and their grandmom to be able to do that, and do it together!

IT: Which destinations would you suggest for independent travel for family groups?

CC: My wife and I are outdoors people and there is so much for families locally with state parks, Forest Service land and national parks. We recently went to Mammoth Cave National Park in Kentucky and had a brilliant (and literally “cool”) time exploring the caves. Cities like Boston and Washington D.C. are iconic destinations with a wealth of museums and history for kids and adults alike, but also great lodging and food and shopping. For the adventurous, there is always big, beautiful Alaska. Quebec is excellent and readily accessible from the U.S. but a very European experience. For the more adventurous, I’d suggest Iceland and Namibia.

IT: What tips do you have for an independent multigenerational group to ensure a successful trip?

CC: Independent travel offers the greatest amount of flexibility and spontaneity, often at the best possible price. However, it does take quite a bit more time to research and plan. I would certainly do as much research as possible, leveraging some of the great family travel blogs out there like WanderingPod.com, MyFamilyTravels.com and CiaoBambino.com. (Editor’s Note: Our sister site, Family Vacation Critic, is another useful site to check out.) Also, the destination’s own websites can be great resources. Visit Costa Rica has a good example of this, with an entire page devoted to family travel. VisitMaine.com has some great search options for family travel too.

I will say, while I love independent travel, booking family travel with a small, independent tour operator can come in very handy, while still providing a true, authentic experience for small groups. We planned a trip to the interior of Costa Rica through JourneysInternational.com, which has been running family trips for more than 30 years and is family owned. The itinerary was perfectly balanced, with just enough activities to keep us all engaged, but also with the perfect amount of down time for naps, reading books and playing in the pool.

IT: How do you balance the travel needs and interests of younger generations with older ones? In other words, how to keep peace, so that, say, the teens get their screen time yet the grandparents get real face time too?

CC: During the trip, the key thing you need to do is respect the pace of your itinerary. You can’t run your grandparents or smaller children ragged with an aggressive, “let’s see it all” itinerary. While we generally like to limit time spent on devices with our kids, when we are in transit or in a hotel room, the kids can use the devices as much as they like. I will say that for long-haul flights, devices like iPads and the seatback entertainment systems are a godsend. Teens can be a bit more of a challenge, as they tend to be more aloof and get bored more easily. But the beauty of multi-generational travel is that it naturally brings about face time, forcing it actually. When you are stuck on a train or bus, there’s so much to watch, talk about, etc. that it naturally breaks down barriers and brings people together around their shared experience.

IT: Where are you and your family planning to go next?

CC: We’re looking at Panama and starting to plan a trip to South Africa too. I can’t wait to take my girls on safari — it will blow their little minds!

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