Traveling with extended family is a delightful challenge—here’s how to make it even better

A few years ago, my parents, siblings and I decided that, instead of getting each other a bunch of holiday gifts, we would take a family vacation together. Since then, we have gone on more than one family vacation with grandparents and cousins, each one memorable in its own way. I have no doubt that these extended family vacations with grandparents and cousins will be “happiness anchors” for my kids for decades to come. They are an absolute delight. They are also a challenge—in a way that traveling with three to four other families, half a dozen kids, and multiple generations can be a challenge. But the payoff makes it worth the planning hassles and any hiccups along the way.

As a child, my grandparents joined us on almost every family vacation. Not only was it a wonderful grandparent bonding experience, but these adventures created some of my most lasting memories. These are the family vacations that stick with you. The ones that embed themselves into your memory and into your soul. Even the chaos that happens along the way (newsflash: there will be chaos) become funny stories in the end. 

Related: To the parents worrying about taking your kids on a flight—you can do this 

There are a few things you can do to make a family vacation with grandparents and cousins as enjoyable as possible:

1. Set a budget and timeframe

No one likes to talk about money, but the sooner you can get on the same page about how much to spend and who will pay for what, the better off you are. Once you’ve set a budget, stick to it. This can be difficult to do, but nothing can cause hard feelings to fester like financial disagreements.  

The same goes for timing. School calendars and work commitments can make finding a time when everyone is available tricky. Some parents might have bountiful PTO and others might have a harder time getting a few days off. Kids’ school breaks might not overlap. Because scheduling can be one of the biggest hurdles, start planning early. You may also want to consider staggering your arrivals and departures with a few days of overlapping time. 

2. Consider the vacation styles of everyone involved

Often there are different—and conflicting—vacation styles when you travel with a bigger group. For instance, maybe one family has early risers and another family likes to sleep late. Some children might want to spend the day at an amusement park; others might want to go to the beach. Some people might like to go-go-go on vacation adventures; others might like to laze and lounge about.

Be honest with yourselves about all of these vacation styles before you decide where to go and what to do. For instance, if a few people in your group have difficulty being on time, you might not want to take a vacation that requires you to be prompt for tours or dinner reservations. If some folks are active and others like to lounge, consider an all-inclusive beach resort that offers add-on adventures and activities.

3. Delegate and take turns planning

When we have gone on a family vacation with grandparents and cousins, we often take turns with planning. For instance, my family might choose the dinner plans one night, my brother’s family the next night, my sister’s the next and so on. We all agree at the outset that the choosing family pays and pledge to not complain when it’s not our night to choose. 

The same thing can be done when it comes to planning how you’ll spend your days. Depending on the ages of the children traveling in your group, you could also delegate planning responsibilities to the children for an afternoon or two—which can be a great excuse to act like a kid again.

4. Set realistic expectations

I have found that this can be one of the biggest challenges, second only perhaps to setting a budget and scheduling. As they say, family vacations aren’t really vacations at all, but trips. This sentiment is even more accurate when traveling with a larger group of cousins, grandparents, aunts and uncles. The more realistic you can be with your expectations, the less risk there is for disappointment. Some of the most enjoyable trips we’ve taken with grandparents and cousins haven’t been the bucket list-type vacations but the ones where we had no expectations other than being together.

Related: You *can* go on vacation with kids and actually relax—here’s how

5. Consider physical needs so everyone can be comfortable

When traveling with a group, especially a group that spans generations, there are often different physical needs. Does a grandparent use a walker? Does a child need an afternoon nap? Does a parent need to nurse a baby frequently? 

For instance, my dad is in a wheelchair so when we travel with my parents, we only consider those hotels or rental homes that are wheelchair accessible. If you have children who need a nap or go to bed early, you may want to consider a vacation rental that has plenty of quiet sleeping space.

6. Build in time alone

You don’t need to be an introvert to need some alone time when traveling with large groups and multiple families, so plan ahead and build in some alone time. Whether it is a morning walk on the beach by yourself, a dinner with your spouse, or an afternoon outing with your immediate family (partner and kids), having some quieter down time will make the time with the larger group more enjoyable. 

7. Be flexible

It wouldn’t be a family vacation without a little chaos. People get sick. Luggage gets lost. Plans get derailed. Having a “Plan B” in mind before traveling can be helpful, but in my experience, what is even more important is the willingness to be nimble and adjust plans quickly and easily—with minimal grumbling. 

8. Capture the memories

Hold on to the magic of a family vacation with grandparents and cousins with mementos and photos. Grandparents love to get photo gifts from these vacations too, so it really is the gift that keeps on giving.

9. Embrace the chaos

Easier said than done. Believe me, I know. But there really is beauty in the messy chaos of traveling with a big group of cousins and grandparents.

Enjoy!