The Ultimate Guide to Multi-Generational Travel

My family traveled a lot while I was growing up, and it wasn’t unusual for my grandmother to join us. In fact, I traveled several times alone with her. While I was in grade school, we took our first trip to Greece. Not long after that, we went on a Caribbean cruise. Some of my best memories are from the times we spent exploring new destinations together.

Even after I had kids of my own and began taking them on vacations, I continued to travel with my grandmother until she was well into her nineties. The older she got, the more challenging it became to arrange the logistics of our trips. But it never deterred us from visiting far-away places. On her 96th birthday, my children, my husband and I sailed out of Venice on a cruise with her to celebrate.

I learned a lot during my travels with my grandmother — including how to ensure everyone has a wonderful time even when you’re dealing with an entourage covering several age brackets. It can be done! It just takes a little thoughtful planning, conscientious communication and shared dedication to making spectacular memories together.

Choose Where to Stay

Where you stay can make or break a multi-gen trip. Your best bets? Resorts, vacation homes and cruises. My family and I have stayed in large resorts that offer villa- or suite-type accommodations. These properties also feature many activities and amenities that are suitable for all ages. And renting vacation homes — with plenty of room to spread out and relax — can be perfect for large groups.

But cruising is my favorite way to vacation with extended family. It allows you to see multiple destinations in a short amount of time and, because your hotel room moves with you, you and your family will only need to unpack once. Another plus? A cruise does much of the planning for you. We always knew where we were eating dinner and what port was the next stop on our itinerary. On top of that, our kids had the freedom to explore, but were never able to wander too far from us.

Adjust Activity Levels

On a multi-generational trip, you want everyone to be able to keep up, but not at the expense of having a good time. When traveling with my grandmother in her later years, we frequently modified our sightseeing plans to accommodate her inability to walk long distances. Instead of walking several miles in one day, we would opt instead for a bus or a trolley tour. Once, my husband even arranged for a motorized rickshaw to take us around the tricky cobblestone streets of Malaga, Spain.

Quick Tip:

If you’re traveling with an elderly relative who has limited mobility, look into the possibility of renting a wheelchair or an electric scooter when you arrive at your destination.

Create Options

You don’t want to over-pack your itinerary — it’s a vacation after all! But you should plan at least a few activities in advance. Choose a destination that offers something for everyone: small children won’t likely want to tour an art museum, and elderly grandparents might not want to spend a day at a theme park. We usually compromise, allowing the youngest in our group to pick one activity, like the zoo, and letting the older kids take snorkeling or surfing lessons while the adults relax.

Give Downtime Some Due

Plan to take a break from each other! Too much togetherness can ruin even the most epic family trips. One of our most successful multi-gen getaways involved renting an oceanfront home on the Outer Banks, in North Carolina. It afforded us the opportunity to spend time together making meals, playing games and swimming in the ocean. It also meant we didn’t all have to get up at the same time to go out to breakfast, which was great for the early risers and my teenagers who prefer to sleep in. We often broke off into smaller groups for walks on the beach, bike rides into town and sailing on the bay.

Quick Tip:

If the kids need a nap, grandparents are usually happy to stay behind and rest, too. This is a great opportunity for parents to slip away and spend quality time alone.

Make Memories

I bought a “grandparent’s book” for my grandmother to take on one of our trips. The journal had a place for her to record her personal thoughts and memories. To help spark interesting discussions, it also contained questions like: what are the most important things you learned from your mother? Or, what did your childhood home look like? My children enjoyed interviewing my grandmother, and we each took turns writing down her responses. Documenting her stories gave us a unique glimpse into her life and helped to focus the trip on what mattered most: spending time with loved ones and weaving memories that will never be forgotten.

Quick Tip:

Preserve your vacation memories. Create photo books and save them for holiday gifts. Your family will love these treasured keepsakes.

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Dana F. is a travel journalist living in Vermont.