10 Ways to Survive a Multigenerational Vacation

A few years ago, we took our first-ever multigenerational vacation. My husband and I, my parents (who hadn’t been to Europe in 40 years), and our two kids, ages 5 and 10 (at the time), jumped right in with a two-week trip to the Mediterranean. The vacation involved coordinating two international flights from two different cities, two separate hotel stays, and a cruise. Everyone told me we were nuts, and at some point during the planning phase, I began to think they might be right… but we prevailed!

The laughs and adventures we experienced on this vacation more than made up for the headache or two we suffered during the planning process; we shared the most amazing experiences together. Watching my son and his grandpa hand-in-hand winding their way through the ruins of Pompeii and my daughter and her gram giggling over gelato on the Spanish Steps in Rome—these are memories I will cherish for the rest of my life. Here are 10 tips to ensure your own extended family adventure is every bit as successful.

1. Get Everyone Involved

This point may seem like a no-brainer, but it’s critical. If someone says “I don’t care what we do, you can decide,” they don’t mean it. Or if they do, they won’t mean it once they get there. Even if some family members are more well-traveled than others—or just more outspoken—make sure you involve everyone in the planning process. Each person should contribute one thing they really want to do or see, and make sure they get to do it. Not only is this important to ensure that everyone has fun, but it also prevents one person from taking responsibility for the whole family’s good time. Kids, even young ones, will love feeling like they are a part of making the trip a success.

2. Choose Accommodations to Suit Your Style

There’s no right or wrong choice on accommodations—the key is to discuss your options with everyone in your group. Maybe you are the type of family who will enjoy one large suite or a vacation rental, ideal for fostering togetherness, or perhaps, separate hotel rooms work best for your brood. Either way, don’t leave it to chance. Talk about preferences beforehand and respect requests for privacy. A vacation rental offers the best of both worlds: separate sleeping arrangements with common living spaces. Rentals work really well for families with infants and toddlers, as there is always a quiet space for naps. In hotels and on cruises, adjoining rooms/cabins are a great idea. Be sure to ask about group rates for large families!

3. Plan Something for Everyone

Whatever time of year you’re traveling, make sure you have plenty of different activities from which to choose, as well as ones with varying degrees of “difficulty.” And don’t expect everyone to participate in every activity. If you want to plan a hike, biking adventure or boat ride, great, but be sure there’s something for those who don’t want to participate, so they aren’t stuck back at the rental or hotel with nothing to do. Also, be sure to plan a few activities that everyone in your family will enjoy doing together. For my clan, it was dinner and a show. The wider the age range in your extended family, the more options you’ll want to consider. Renting a home on a secluded beach miles from town may seem idyllic to you, but your own idea of idyllic can translate to boring pretty quickly for both the older and younger members in your extended family.

4. Be Realistic

You don’t need (or want) a month’s vacation. Unless your family members are pros who travel together all the time, a week or two is probably plenty when it comes to a multigenerational trip. In fact, two weeks is the absolute max for us; that’s right about the time when everyone says, “This has been amazing! Let’s go home.” If you stay much longer, family dynamics may start to unravel. Chances are, you won’t be able to swing more than that anyway.

5. Share Your Packing Lists

On our recent trip to Europe, my mother and I realized too late that we had packed two of everything: two hair straighteners, two tweezers, two nail clippers, two bottles of Tylenol, two boxes of Band-Aids… you get the picture. While you can’t share everything, there are a great number of items that can easily be communal property—especially among family. When you’re traveling long distances and lugging and paying for extra bags, sharing can be really useful. Make a list of the items that make sense to share and decide who will bring each. Heck, you can even share clothes in some cases. Other items that you might share: hair dryers, curling irons, laptops and toothbrushes. Just kidding.

6. Take a Break

Don’t mistakenly think this will be a relaxing vacation. It will be loads of fun, but it probably won’t be relaxing. And even the most tightly knit families will get on each others’ nerves eventually; things that never bothered you at home will bother you on the road, so be sure to schedule some time apart. Maybe the grandparents can enjoy an afternoon by themselves while others hit the beach with the kids. If you have more than one child, divide them up among the grownups, so each feels like the center of the universe for a day. Regrouping at the end of the day and sharing your stories over dinner is great fun. We made sure to end the trip together, enjoying a special dinner on our last evening away.

7. Be Clear on Finances

When planning a multigenerational vacation, consider everyone’s budget, and make sure to discuss who will pay for what. Often, these types of trips are gifts, with one party footing the bill for the whole group. But inevitably, there are additional and unexpected expenses. Regardless of who has booked and prepaid for the vacation, be sure to discuss all the possible additional expenses, not just the major and obvious ones like airfare and hotels. Are meals included? Drinks? What about activities and excursions? Who will pay for those? What about tips? And don’t forget about transportation once you get there. If you’re planning on taxis or Uber, there’s a good chance you won’t all fit into a single vehicle.

8. Don’t Overtax the Grandparents

While it’s great to have grandma and grandpa around to play babysitter, their idea of a vacation might not involve staying in with the kids every night while mom and dad go out on the town. Have this discussion beforehand. Even if they insist, be sure to fit in time for them to get out alone for dinner one night, too. Our family loves resorts with kids’ clubs, so that when all else fails (and even when it doesn’t), there is always someone around to entertain the kids.

9. When in Doubt, Ask an Expert

We find that making the arrangements on our own is part of the fun; but if you’re feeling a little unsure, or having trouble agreeing, you might prefer to have someone do the planning for you. There are tour operators that can help you plan a trip that appeals to all generations (check out the 7 Best All-Inclusive Multigenerational Tours for some of our favorites). Make sure you inquire about group rates and other discounts for large families.

10. Capture Every Moment

If your family is anything like my family, multigenerational trips are, sadly, few and far between. Busy schedules prevent us from getting away together very often. By the time the opportunity comes around again, my oldest will likely be in his teens. So, take a million pictures. Take a million videos. And then take some more. And make sure you ask a few trustworthy strangers to snap a photo of your entire crew. My all-time favorite picture from our vacation is one of all of us taken by a lovely Italian lady we stopped on the street by Trevi Fountain. When you return home, let the kids help make a scrapbook. If one person picked up the tab, this is also a great idea for a thank-you gift!

There’s no right or wrong when it comes to choosing a destination, only what works for your family. Beach vacations, ski vacations, cruises, and even dude ranches and theme parks can make great multigenerational trips, if you plan wisely. Remember, don’t underestimate your elders! My parents had at least as much stamina trekking around Europe as we did. We had such a successful trip that I’m already brainstorming ideas for our next adventure—and hoping to extend it to even more people this time around. Wish us luck!

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