How to Plan a Multi-Generational Vacation (Where Everyone Stays Happy)
We’ve traveled a lot since our kids were born. We made it a priority and traveled many ways. Between RV camping, a few long-distance roadtrips, and more than a dozen cruises, we’ve experienced a lot and built lasting memories. And through most of our travels, we’ve had my in-laws with us.
Three generations, sharing our love for travel.
The heart of our travels: bringing the generations together to explore the world.
When it comes to cruises, we identified our signature approach early on by pairing a cruise with added land days before and/or after the cruise. Through most of these trips, my in-laws and kids have been with us. And I can confidently tell you that we’ve always had the best interests of my in-laws and kids at heart while on these trips.
So, how do we keep the whole family happy when there’s such a wide age gap? Let’s be real – we all know the struggle of trying to entertain kids and grandparents at the same time.
It’s by paying attention to their interests and pace. We don’t expect three generations to be tied at the hip.
We call it the “split and reconvene” method. Let me explain.
When we were in Florence, Italy, we decided to visit Brunelleschi’s Dome. Although breathtaking, it requires you to walk up 463 steps, pass through narrow passages, and be prepared for low headroom. Knowing all of this, my in-laws decided to stay back.
So, what did they do while we climbed? They stopped at a nearby Italian coffee shop and sipped espresso while they people-watched. Perfectly peaceful and relaxing. After our climb, my in-laws felt rested and ready to explore Florence.
Another time, we were on a cruise ship with my entire extended family, and we planned an all-day off-roading excursion in Iceland. My in-laws decided to skip the bumpy terrain and stayed on the ship instead, taking advantage of everything it had to offer.
High-energy adventure for the kids, peace and quiet for the grandparents—everyone wins.
Designing an itinerary for your group, not just the destination.
Who you travel with determines how you should plan. The secret to a successful multi-generational vacation is building an itinerary around the unique dynamics of your group, rather than trying to force everyone into a rigid schedule.
By embracing the "split and reconvene" approach, you remove the guilt of staying behind and the pressure to keep up. It gives younger travelers the freedom to hunt down high-energy adventures while allowing grandparents the space to enjoy a destination's slower, richer moments at their own pace.
A vacation with multiple generations takes more coordination upfront, but the reward is entirely worth it. When everyone has the freedom to choose their own pace during the day, the time you spend reconvening around the dinner table to share stories becomes the best part of the trip. Happy planning!