What to Consider When Planning a Multi-Generational Trip

Maybe the grandparents want to take everyone on a cruise--but the kids think they'll be bored.

Perhaps you're thinking of a beach vacation with friends who are in different stages of life. One couple is worried about leaving their toddler, while another couple is counting how many bars they can hit the first night.

Possibly, you're considering a cross country trip with your teenagers and their eight-year-old cousins, only the teenagers think their cousins are smelly and annoying.

Planning a vacation, stay-cation, or once-in-a-lifetime trip is already hard enough. When you throw in nap schedules, moody teenagers, set-in-their-ways grandparents, and frazzled parents, that dream vacation may end up looking more like a nightmare.

Whatever the ages and life stages of your potential travel partners, I'm here to tell you that it is possible to go on a trip where everyone ends up happy. Doing so will require a bit more planning, but you may end up having the greatest time ever.

6) Survey the participants before you leave. 

Before any tickets are booked or activities are planned, it's good to have a meeting (or email chain) where everyone shares what he or she'd like out of the trip. If the grandparents think it's going to be a relaxing, poolside vacation while the kids want to get out and explore the local sites, there will be conflict at the destination. By learning about everyone's expectations ahead of time, you'll be able to plan a little bit of what everyone wants.

5) Make sure everyone understands the details. 

Once everyone is comfortable with the dates and proposed activities, you can email or mail a complete list of costs, dates, and times. This cost-based itinerary ensures that everyone going knows how much to save up in preparation--and if the initial cost is too high, those looking for a more budget-friendly hotel or activity can make plans far in advance.

This itinerary also covers arrival and departure dates and times, so Aunt Susan won't have a reason to complain when she misses the flight everyone else is on and has to book a later one. Especially if you're on a tight schedule or if you're dealing with a large group, it's important to keep reminding everyone of where they should be.

4) Know your fellow travelers' limitations.

If your brother and sister aren't getting much sleep at night because of their three-month-old's schedule, it's probably best to build in a nap time for them to rest. The same goes with older, less mobile grandparents: they'll want to be involved with what the family is doing, but they'll also need some downtime.

While you may want to take advantage of EVERY.SINGLE.MINUTE of this incredible vacation, it's okay to slow down if other members of your party require it. Or, if everyone is fine with the arrangement, plan an optional activity that's better suited for families with older kids in the middle of the day: that way, some people can nap while others continue to enjoy the location.

3) Find activities that have different levels of participation. 

Some locales, like cruises and family all-inclusive resorts, seem tailor made for a multi-generational trip: there's almost always something going on for whoever wants to participate.

But don't think that you have to choose one of those destinations if you're looking for a vacation everyone can enjoy. A waterpark offers a lazy river for the grandparents and crazy, gravity-defying rides for the teenagers. A trip overseas offers art museums for the culturally-inclined, and pub crawls for those looking to experience a city in a non-traditional way.

Not everyone has to do everything! Layer on experiences, have set meeting times or dining reservations, and everyone can explore the location in the best way for him or her.

2) Have the generations work together, rather than in opposition. 

If the grandparents, the aunts and uncles, the toddlers, and the teenagers are all heading out together, the generational gap between everyone can quickly cause conflict. Instead of emphasizing the differences of the people on your trip, highlight what each generation can offer the group.

Have your parents or grandparents share their memories of World War II and D-Day when you visit Omaha Beach. Then, have the young ones in the ground help their grandparents use their audio guides, or navigate the smartphone app connected with a particular site.

1) Be flexible. 

No matter where you're traveling or with whom you're traveling, there will be hiccups: Grandpa Martin will forget his reading glasses back home, or 4-year-old Elise will have a melt down in the middle of a tour.

It will happen, I promise. It's happened to me! After he had a fit and refused to walk with the rest of his family and me, I once drug a five-year-old through the British Museum on his rear end. His corduroys slid very well on the marble floors. (True story.)

No matter what transpires, just be flexible. And while I don't condone hauling people around museums, sometimes you've got to do what you've got to do. If you need to go back to the hotel room, take a few minutes and rest. If you think your child is overstimulated, pull him or her aside for a coloring session while everyone else finishes looking at the play.

Remember: it's your trip, but it's also everyone else's trip, too. Work together, communicate, and you're well on your way to having the trip of a lifetime!

Have you ever taken a trip with people in other life stages or from multiple generations? How did you make the trip work? What would you do differently next time?