How to survive a multi-generational family vacation (without losing your mind)

by Greg Benchwick · Jul 30 2014

Grandma wants to go to the quilting museum, your spouse is mostly interested in romantic dinners, the kids couldn’t give two shakes about this trip of a lifetime, and the dog, well the dog just ate some chocolate from grandpa’s bag and is throwing up.

Traveling with the entire family is an enriching, challenging, exhausting and wonderful experience. And while Jerry Seinfeld was right – there really is ‘no such thing as fun for the whole family’ – these tips will help you tailor your multi-generational family vacation to keep everybody moving forward and building those scrapbook memories (and stories you’ll laugh at someday – hopefully).

Choosing a trip for all ages

Not all destinations are created equal. For your ragtag crew, you’ll need to ID a destination that meets the needs of the kids, the partner, the dog, the goldfish, your Aunt Couie and the older generation. But don’t be surprised if grandpa really wants to go waterskiing while your 25-year-old cousin is more interested in hanging out poolside.

Your best bet is to guide (but not control) the planning process. When my daughter, Violeta, was born in Rome, everybody wanted to come for a visit – not just to poke and prod the little ball of mush that we all adored, but also to see the incredible sights that make Italy a top world pick (even the Griswolds made it here in the classic comedy film European Vacation).

Europe’s got it all – churches and art for culture hounds, chic restaurants for romance seekers, and built-up infrastructure to make sure everybody won’t get lost (identify your wanderers early on – and short of GPS tagging or leashes, make a meet-up plan for later in the day).

Keeping it close to home makes it easy. I was living in Italy at the time, working as a bureaucrat for the United Nations, and had plenty of time to lay out our trip. But the destination needs to meet your family’s unique dynamics. In-fighters might choose a place with lots of guided activities, procrastinators should book everything at once, blame-placers might opt to hire a travel agent to book the trip, and perfectionists should find a place where perfection just won’t stand – say the medina in Marrakesh.

Finding a theme is also important. Some of my best experiences with the whole family have taken place in US National Parks. There’s a visitor center for grannie, easy hikes for the kids, and enough space for even the biggest of egos to roam free. You can also theme trips around museums and art, adventure and activities (try being mad at your sister when you are flying at 100mph on a zipline), or food and wine (booze of course being the universal lubricant to keep any family vacation from going kapooey).

And I try to avoid rougher destinations with the whole family, opting instead for unique takes on mainstream attractions.

To start the planning for Italy, we picked a time that worked for everybody’s vacation schedule. Then I asked each person what they’d like to see – we had a sister and brother-in-law, a new mom, dad and baby, grandma and grandpa, and a three-legged Turkish street dog in a mish-mash entourage I’d later dub ‘Generation Holy Crap’).

Half the crew had already visited the northern tourist circuit from Rome to Florence and across to Venice, but we were traveling during Christmas time. I figured a winter take on these classics would still hold plenty of interest. And just imagine Venice in the snow (enchanted, empty, everlasting and eternal).

Sometimes it pays to take control (and sometimes you got to let up). Your lodging choices largely depend on your family dynamic. I knew that mommy, baby and I needed our own room, but that our newly minted nonna (grandma) would want as much family time as possible.

Vacation rentals and small B&Bs are perfect for this. We ended up renting entire agro-turismo chalets just outside the major cities. Staying in the countryside meant more space to roam for the dog and allowed for a bit of separation if mom wanted some alone time with our precious Violeta, while the rest of the crew headed out to explore the cities.

Every dinner on our Italy trip turned into de facto planning time for the next day. Over the three or four courses, we would check the guidebooks and internet, talk about where we’d like to go and set up groups to tackle the various wants, needs and desires. I am a horrible planner – shameful admission for a professional travel writer – but my sister ‘Caraboo’ can plan out an itinerary from 6am to midnight no problem. Let your talents rise.

You don’t have to be together 24 hours a day (in fact, you’d better not if you want to make it home alive). Make sure each person has the opportunity to carve out their own personal time.

And sometimes you have to be a bit dictatorial if you are the group organizer (and in my view, each family vacation does benefit from one central shot caller, tie-breaker and munificent Protector of the Realm). This said, each family member should have a chance to plan one portion of the trip. Nonna, for instance, loves churches, so I asked her to map out our course in Padua. My sister and brother love food, making them ideal to lean on when picking a spot for dinner.

As my daughter’s gotten older, I’ve allowed her to make more plans for our trips as well, guiding her choices with smart options that work for the rest of the crew. Do you want to go to the beach or the museum today? Want to play the sign game on our drive this afternoon or just sing songs? I heard about a treasure in this museum, let’s see if we can find it.

Survival tips

‘This is no longer a vacation,’ says Clark W. Griswold in Family Vacation. ‘It’s a quest for fun. You’re gonna have fun, and I’m gonna have fun… We’re all gonna have so much fun we’re gonna need plastic surgery to remove our smiles!’ Sound familiar? Here are some ideas to break the tension, when it all gets a bit too much.

Have a safe word. It works for the S&M crowd, and it very well could work for you. If things are getting too tense, yell ‘Paparazzi!’
Let tempers cool. So Pappa is peeved that you missed the bus. Let him cool off on his own timetable. The apology will come soon enough.
Take the blame. Don’t be a martyr but dive on that grenade if it’s about to go off.
Separate and conquer. Allow people to take as much time away from the group as they need. Good things come in small quantities, especially when it comes to family.
Little pleasures. Take care of yourself, especially if you are the person in charge. If the captain is unhappy, his crew will be miserable.
Family hug. End each argument with a hug, a laugh and a kiss. You are making memories (good, bad and ugly) and when you get through this, you’ll look back on nearly every moment as one of the best times in your life.
Greg Benchwick is a Lonely Planet writer based in Colorado. He and his daughter – along with a new 100-pound Anatolian shepherd, Nonna, Abuelo and Pappa George, Tia Boo and Tio Bry, and his 30+ cousins still take trips together. They are even friends on Twitter and Instagram. Check in on their adventures on Twitter @greentravels and Instagram @lonelyplanetauthor.
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