Steve Evans

I come from a big family, and we all looked forward to our annual trip. We would begin planning these a year in advance, and some of my best childhood memories are those journeys, so I know how important multi-generational travel can be.

One of the keys to a successful trip is finding activities that will engage everyone in the family. For many, Alaska is an ideal destination, and there are many ways to enjoy it. One adventurous family asked me to rent two Winnebagos for their group. They have traveled together a lot, and everyone was quite fit, so it worked out well.

For most groups, though, a cruise is a better choice, especially when there are varied interests and ages. People can spend time together on a cruise, but they aren’t forced to be together 24/7, all doing the same things at the same time. Kid- and teen-programs can also be a plus for both the kids and the parents. I have extended families that cruise together every year.

Usually, I suggest that families leave their days unstructured so everyone can follow their own interests during the day—whether it’s shore excursions, activities, or spa treatments. Dinner should be the time everyone commits to being together, and the easiest way to do this is to reserve a table every evening at a set time. That way, there is always family time, and people can make plans to do things together the next day if they want. Most multi-generational groups love that.

Another nice thing about cruises is that they can be very cost efficient. Often I can arrange a group rate and other value-added savings. For example, on a recent Alaska cruise for a family of 18, I booked them into eight cabins. The total price was $3,000 less than they’d expected, based on their online research. 

All-inclusive resorts can also be great for families. As with cruising, family members are free to enjoy separate activities but still gather for dinner every evening and plan a few specific activities that they want to share. The Riviera Maya has some great resorts, and families can take some memorable excursions. One family still raves about exploring Chichen Itza together. 

Each group is different. For some, a stay in Paris with everyone based in the same hotel can be wonderful. For others, a ski vacation staying at a villa in Vail is perfect. In planning a multi-generational trip, it is important to consider everyone’s interests, activity levels and preferences. That is an important part of what I do as a multi-generational travel specialist. That way, I can plan a trip that everyone will remember with joy for years to come.