My 5 Unbreakable Rules for a Successful Multigenerational Family Vacation

I’m blessed with a close family. We enjoy one another’s company so much that we vacation together as often as we can. Since travel is my business, the planning often falls to me. After a host of trips, I have learned a few things and created this list of unbreakable rules.

Be Flexible on Scheduling

This is self-evident if some members of the family are school-age kids, whether that means kindergarten or college. They are slaves to the school calendar and likely will only be able to travel on school holidays. If you want them on the trip, it has to happen when they’re available.

Not being beholden to the school schedule, however, does not mean you are home-free. Chances are there will be some member of the family who has limited vacation time – a young adult who has just started a new job, for example, or an hourly worker whose work schedule is unpredictable.

I think it’s easiest to start with an online scheduling tool like this free Doodle scheduling tool. Everyone can add their own availability to at least narrow down the choices. Then you can move to a group conversation in person or via Zoom to finish the discussion.

Be Honest About the Cost

There are many ways to pay for a multi-gen trip. I’ve heard of families where Grandma and Grandpa treat everyone to the trip – one friend’s in-laws celebrated their 50th wedding anniversary by paying for their three kids, their spouses and all the grandkids to go on a Disney cruise.

And then there’s the way we do it in my family: Everyone pays their own way.

Both approaches have their benefits and drawbacks.

When the grandparents pay, it can mean they expect something in return: that everyone will show up, be happy and do what the grandparents want them to do.

When you do it the way my family does, it means some people have to compromise. We set the budget to ensure that every family can afford the trip. The wealthier families can treat themselves by booking a suite at the resort or taking themselves out to a fancy dinner one night.

Accommodate Everyone’s Needs

My mother-in-law is blind, and my father-in-law had some mobility challenges toward the end of his life, so when we decided on a family trip to an all-inclusive in Mexico, we chose the smallest one with the shortest walk to the beach and the calmest surf.

It meant that the teens had to compromise on a resort that offered fewer activities and amenities. But they got more time chilling on the beach, and we arranged for an off-property trip to swim in cenote.

Plan for Time Apart

It’s tempting to think that everyone needs to spend every minute together when you’re on a multigenerational family vacation. That’s why you’ve planned a trip together, right? Wrong! You planned the trip to spend MORE time together, but that doesn’t mean you need to spend ALL of the time together.

Everyone should be able to have the vacation they covet. While that might mean they want to spend every minute with you, never assume that is the case.

Always build time into the schedule during which each family member has the option of doing something on their own. The athletes can spend time being active. The couch potatoes can spend time lying on the beach. The youngest and oldest can spend time napping.

Having said that, remember that is supposed to be a family trip. That means it’s reasonable to require everyone to spend some structured time together – dinner each night or one excursion or activity you all agree to do together, for example.

Don’t Make One Person Do All the Work!

This is a lesson I learned the hard way. We were headed to a niece’s wedding in Dallas, so I agreed to squire around my husband’s 82-year-old mom, his 80-year-old aunt, hubby and our two teens for a 3-day tour of Dallas after the wedding.

After three days of managing six people, ranging in age from 15 to 82 – everything from getting them through airport security to managing museum entries and local transportation – I was completely exhausted. They, however, loved it. As we were waiting at the gate to board our flight home, they asked where we could go next.

I dredged up one more smile and responded, “An all-inclusive resort.”

What’s Your Experience:

Have you taken a multigenerational family vacation? What worked best for your family? What would you never do again?