Arranging private travel for multiple generations is a wonderful way for families and friends to connect, but requires an extra layer of planning to ensure everything goes as smoothly as possible—and that’s true now more than ever. We’ve gathered some tips on how to plan a vacation that appeals to every age group. 

Set some ground rules

Assessing everyone's risk tolerance is a good starting point, especially if your group includes travelers who are immunocompromised or unable to be vaccinated. Consider what precautions should be taken to put everyone at ease. Will you all agree to take COVID tests before traveling (even if your destination doesn't require it)? Will you wear masks in crowded spaces? Plan meals and activities that are mostly outside? By discussing concerns and solutions ahead of time, you can set some ground rules that everyone agrees to follow, ensuring all the members of your group are safe and feel comfortable.

Find shared interests

Large age gaps can seem like quite a barrier when deciding where to plan a trip, but don’t let that stop you. Whether a parent and teenager both enjoy outdoor activities, or a grandparent and grandchild both want to learn more about the history of a new place, there’s always something that can tie two people together. For example, a great connection between familial generations is a family’s heritage. What better way to draw multiple generations together than to learn about your family’s roots?

Plan something for everyone

This tip is especially important on trips that include more people. Although it’s important to find something in common, there will always be discrepancies between generations. It’s a good idea to plan a few different optional activities for each generation to choose from. There will be plenty of time to spend together throughout your trip, so why not let adults do what they want while grandparents get some time alone with grandkids? It’s good to have a balance between spending too much time together and spending no time together at all. This is especially important to remember if not everyone in your group is at the same fitness level. If you booked an intense mountain hike, have a backup option for grandparents or anyone who’s not quite up for something so strenuous.

Discuss finances ahead of time

This rule is especially important for large multigenerational family trips, since money lines can often be blurred. Who pays for which activity? What if someone wants to pick up the group’s dinner tab? It’s natural for grandparents to want to spoil their grandkids or for one member of the family to be more generous than others, but money should be talked about before the trip. It’s inevitable that some members of the party will be on a different budget than others, but that doesn’t mean you can’t be open about money. Additional and unexpected costs always come up during vacations, especially with larger parties, so it’s smart to be prepared ahead of time.

Be flexible

It’s only natural that members of your intergenerational party may disagree. It’s often easy for each person to have a “my way or the highway” attitude, but that will just cause stress and annoyance. Do your best to plan ahead and include everyone in the planning, even younger kids. If everyone is having trouble agreeing, try giving each person a day to plan the group’s itinerary, or have members rotate daily responsibilities: where to go, what to do, what to eat, etc. That way, everyone gets a chance to make decisions and try something new and unexpected.

Originally published November 2017; last updated September 2022