Why multigenerational travel is on the rise

Erica Terry

If you’re like many parents, you’ve considered taking a multigenerational trip where kids, parents, and grandparents can spend time together, make lasting memories, and truly enjoy themselves.

This appeals to families for many reasons. A grandparent gets to watch their grandchild experience something brand new for the first time. It’s a meaningful way to celebrate milestones like birthdays or anniversaries, and a beautiful opportunity to bring together generations who may not live near one another.

Time moves quickly. Kids grow fast. Parents age. Memories, however, can last a lifetime. More families are realizing that the best gift isn’t another holiday present — it’s shared time together.

That’s where I step in. I help families plan multigenerational trips, and this style of travel is one of the fastest-growing trends in the industry. Families are often spread across different states. Schedules are busy. Retired grandparents may have more flexibility and a desire to be involved in a meaningful way. These trips aren’t just vacations; they become mini reunions. Planning them requires balancing budgets, personalities, and varying energy levels. It takes strategy to make it all work — and it starts with choosing the right destination.

There are several vacation styles I frequently recommend to my multigenerational travel clients.

First, cruises. Cruising is ideal because you unpack once and settle in. There are multiple dining options to satisfy a variety of tastes, built-in entertainment for every age, quiet adult spaces, and dedicated kids’ clubs. My personal favorite for this style of trip is Disney Cruise Line, but there are many cruise lines to consider depending on your family’s preferences. One of the greatest advantages is that everyone can enjoy the day they want — port excursions, pool time, relaxation — and then reconnect together at dinner.

Second, theme park destinations. As a Disney travel specialist, this is especially close to my heart. Walt Disney World is designed for all ages, from toddler-friendly attractions to fine dining and VIP touring options. When planned correctly, it works beautifully for multiple generations. Proper pacing, thoughtful dining reservations, strategic ride planning, and selecting the right hotel make all the difference. I help families coordinate each of these details so the experience feels seamless.

Finally, all-inclusive resorts. These are wonderful because each guest can pay upfront and relax without worrying about splitting checks throughout the trip. Grandparents can unwind, parents can unplug from work, and kids remain entertained. There are excellent family-focused all-inclusive resorts in the Bahamas and throughout the Caribbean that cater to a wide range of travel styles.

Of course, there are hidden challenges. Mobility concerns, picky eaters, dietary restrictions, differing budgets within one family, unique room configurations, travel insurance for older travelers, and coordinating arrivals from multiple airports can quickly complicate things. This is where my expertise makes a difference. I untangle the logistics so families can focus on being together.

The magic of these trips is the togetherness; the success is in the planning. Photos may fade over time, but the memories do not. There is lasting value in shared experiences, and the window for gathering everyone together is often smaller than we realize. With the right destination, the right pace, and the right structure, a vacation can become a family legacy.

Erica Terry is a Westchester-based travel advisor specializing in theme park destinations, cruises, and all-inclusive resorts. I help families design seamless, memory-filled vacations tailored to every generation. You can reach her at ericat@friendlikemetravel.com.