top of page

7 Steps to Planning the Perfect Multi-Generational Trip

A multi-generational trip can be a fantastic time of bonding and making special memories together. This type of trip helps us see each other in a new light. Johnny may realize Grandma is a lot of fun to be around, and Grandpa may realize the “sullen” teen in the family is an intelligent young man who is great with people.

The last several weeks I have been planning multi-generational trips for groups of more than 10 people, one to Hawaii and another to Alaska. Over the years I have planned these kind of trips for my extended family as well to New England and Canada. If you are wanting to plan your own getaway with the kids and grandkids, here are some key tips:

Set a Budget to Help Make Decisions

While a world of possibilities will exist at first, a budget for the trip will help you narrow things down. A beach trip to Florida or to the mountains of Colorado are both drivable and thus keep expenses down. Hawaii or Alaska are more ambitious, but still in the USA. Bigger budgets could include the Caribbean or even Europe.

Gather Input from All Generations

This is key as sometimes the teen grandkids or smaller kids are left out of the planning process and then we wonder why they’re not having a good time. Each family member may not have strong opinions about where to go or what to do, but asking their opinion ahead of time goes a long way towards their buy-in and enjoyment of the trip.

Decide on the Format that Suits the Group Best

As you can already see, there are a lot of moving parts here and choosing the right format for

the trip is key to overall satisfaction. Some families like cruises or all-inclusive resorts because you only have to unpack once and meals are already taken care of. Other families rent a big house in a resort area and love the flexibility that it provides.

Schedule Some Downtime

If the planner of the trip is Type A and schedules back to back activities, the group will quickly become exhausted and then the meltdowns begin. Not just for the little ones, but for the older family members as well. It’s smart to design a mix of morning and afternoon activities, leaving the other part of the day open.

Moms Are on Vacation Too

If a man is the primary trip planner, he may not think it is any big deal that the ladies do the cooking in a rental house. But that format is no vacation for the ladies, just another day of work. Consider bringing in a private chef to your rental house for some of the meals. A common format is breakfast in the cabin/house, lunch out at a restaurant before or after activities and then a chef prepares dinner for the whole group. There is no waiting an hour for a table for 10 and the cleanup is taken care of as well.

Everyone Doesn’t Have to Do the Same Thing All Day Long

There is this long-held view that if a family goes on a trip together, then they should be together all day every day. That view has wrecked many trips as family members feel constricted and frustrated. Choosing a location with multiple activities gives family members options. The guys can go play golf while the ladies head into town for shopping. The kids can play outside with the Dads while the ladies get spa treatments. Choosing a rental home close to a resort town and considering two rental vehicles goes a long way towards more flexibility.

Start Planning Early

2022 will be the great return to travel and things are already starting to fill up. Don’t wait until spring break to start planning that multi-generational trip for next summer. The earlier you start, the more choices you will have and less stress choosing between available options.

9 views0 comments

Recent Posts

See All


bottom of page