Extended Family Group Walking In Park

Expert Q&A: The Lowdown on Multi-Generational Travel

Watching a vivid sunset, romping on the beach, enjoying long, indulgent dinners—those kinds of travel experiences can be even richer and more memorable when you share them with your extended family. 

Multi-generational travel—vacationing with kids, parents, grandparents and even grandparents—has been a hot trend for several years. Now, it’s more appealing than ever. You can get away, spend time with family members you may have been separated from, and have a built-in social bubble.  

“Multi-generational travel can be magical,” says Kimberly Wilson Wetty, a mother of two and the co-president and owner of Valerie Wilson Travel in New York City. But, she says, it can also be exhausting. 

With a multi-gen trip, you’re not just planning for a larger group—you have to make sure everyone can be happy and comfortable, whether they’re seven months or 70 years old. You may be navigating sibling rivalries or other difficult family dynamics. One paying might be paying the bill, or you could be dealing with several different budgets. 

Wetty specializes in family and multi-generational travel and has curated hundreds of trips for her clients over the past 25 years. She shared her expert advice for planning the most successful—and least stressful—multi-generational trip possible. 

What’s the first thing you need to consider when planning a multi-gen trip? 

The time of year you plan to travel. Most families need to travel around school breaks, and that requires extra planning to get the reservations you want, since many people are traveling at the same time. Count on 12 to 18 months of preparation if you’re traveling at peak times.

How do you decide where to go? 

When it comes to location, there are likely to be many opinions. Too many opinions can be a problem, so I find it helpful to have one or two family members take the lead organizing and working with the travel advisor. Talk as a family in advance about where you might want to go and try to narrow down the choices. No matter how connected the family is, not everyone will want to do the same thing. 

Focus on the “Why” behind the trip and set goals. Are you looking to connect and reconnect, explore, celebrate—or something else? These are the initial questions to ask. Then, from there, you can highlight interests. I’m a big believer that  every family member gets a vote about what they want to do, from about age seven. A good travel advisor can then help you hone in on a plan with something for everyone. 

What should you keep in mind for older family members?

That greatly depends on the grandparents, great aunts and uncles, etc., and what kind of relationships they have with their children and grandchildren. Set a pace that works for everybody! As grandparents get younger in mind, body and spirit, we have moved away from “visiting grandparents” to “traveling with grandparents.” I have many groups where the grandparents have more energy than the parents, who might be time-starved and exhausted from their daily lives. 

Be as transparent as you can with your travel advisor. Realistically, not everyone gets along beautifully. Some families need more built-in “time away” from everyone on the itinerary. Others don’t. In my book, dinner is mandatory— but perhaps the entire day needn’t be spent together. 

Isn’t traveling with a big group a pain? 

Hotels, cruise lines and villa/house rentals are focused on this growing market share, catering to multi-generational travelers by creating more connecting rooms, offering meal plans and activities for everyone and even offering dedicated concierges for family travel. This niche of the market has become much more of a focus than the afterthought it once was. The hotel kids’ clubs of the 2000s have morphed into experiences that families can create and enjoy together. Families want to explore and discover together because that’s what creates lifelong memories. 

What are some great multi-gen destinations—now and in normal times? 

My go-to recommendation has always been a cruise—and it still is. Cruising takes the hassle out of planning. It eliminates travel between destinations, does away with packing and unpacking and limits the countless bills to scrutinize. 

Cruising is perfect for a large group and has the benefit of providing all-inclusive, all-day dining options (nobody has to cook or shop for groceries!), onboard activities for kids, amenities for adults, shore excursions and sports programs with cross-generational appeal. It offers a straightforward way for adults to pick up the tab, too, by pre-paying all costs and gratuities up front. Cruising is on pause now, but my prediction is it will be stronger than ever when it returns. My kids have been on more cruises than we can count, each experience is more special than the next. 

That said, not everyone is a cruiser. Other options I love for multi-generational travel (with kids that are at least 10 years old) are cultural immersion trips to places like Japan and Europe. Alaska is a fantastic multi-gen trip, and so is hiking and biking in the Dolomites. Pretty much anything is possible. 

And, when in doubt, a great beach vacation aways works, too—requests for villas and house rentals are wildly popular, especially in these times. 

Terry Ward is a Florida-based freelance journalist and travel writer.