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How to Enjoy a Three-Generation Family Vacation

Travel Team | Apr 18, 2022

Woman with a baby in a backpack overlooks a scenic bay.

There is nothing I can think of that comes close to the thrill I had one year, way back in 2005, when I finally got to pay my parents back by taking them on a trip to Italy. They had been very helpful in my earliest days as a web publisher and helped me buy the site that I still run today. My girlfriend and I wanted to come up with a way to pay them back that they would never forget. We gave them a memory that they also never forgot.

Travel Italy with La Famiglia

As a result, I got a chance to travel to my favorite place, the Italian countryside, with two of my favorite people and my girlfriend, Cindy. That week in Le Marche, on the Adriatic side of Italy, remains one of my best trips ever.

Why? I wanted to cook with Mom after buying our tomatoes, basil and pasta from a vendor, who only spoke Italian, at the town market. My parents loved hearing Cindy speak in her perfect Italian, explaining things and helping smooth the way in this part of the country with few English speakers.

I wanted to walk ancient streets and talk about Roman history with Dad. I wanted to simply experience a foreign country with another generation and see how they reacted to the surroundings and the thrill of being in Europe that I feel every time I go there. I did that and more, and the time we spent just hanging out in the shady loggia, or attached porch, in the back of the lovely old house in Le Marche was as much fun as I hoped it would be.

Brown church stands atop a hillside village.

Looking back, I still get a thrill recalling the evening village fair we attended, that went long into the night and that my parents stuck through even though they were tired. And the long lunch with that hard-to-describe taste you only get from an old chef working in an Italian country restaurant in a forgotten old village. And laughing as I sped in our new rental car down the slippery curves of the parking garage, with my dad yelling ‘Enzo, Enzo!’ as I drove.

Mom and dad were the perfect traveling companions. They let us go out when they wanted to stay in, and they were never needy; they enjoyed the place as much as we did. The house was surrounded by farm fields with chattering birds, and it was the kind of view you drink in and savor.

One day I remember coming home from the market and seeing both of them kneeling on the ground studying a column of ants in the dirt. They took the time to simply enjoy the sight; my girlfriend Cindy and I laughed.

Give Time with the Grandkids

Another memorable moment with my parents was when they got to enjoy the company of their granddaughter and grandson when we rented a big country house in the mountaintop town of Eagles Mere, Pennsylvania. The house had more than eight bedrooms, and we found the very best and largest for Mom and Dad.

At this time, they were getting older. This was a few decades after our Italian trip, so they puttered around the house, and dad spent a lot of time stretched out on a divan in the large, shady back porch.  He read his books and held court as the grandchildren quizzed him on his opinions of their modern things, and he laughed at their jokes and enjoyed having the little ones sit close to him.

Make Family Vacation Stress-Free

Part of the way a three-generation vacation works is that no one makes anyone do anything they don’t want to, so if Uncle John wants to decline a trip down to the beach and sit on the porch, he does it. If young Sofie wants to walk down to the little store for the fourth time in one day, hey, you give her more dollar bills and say ok. Nobody is allowed to be the bossy one, and everyone can do only what they really want to do without judgment or shame.

Mealtime is a special tradition on these multi-generation trips. Each night a different squad of people is tasked with everything — buying enough food for 21 people, creating the dinner, and doing all of the cleanup. During cleanup, the rest of the family can stay at the table for the sobremesa, lingering long after the dishes are cleared when the great conversations take place and the candles flicker.

Only the designated squad has to get up, and on the subsequent nights, other teams will take the job, so each person only has to work hard for one night. It’s a tradition that provides the most enjoyment and the least amount of hassle for everyone.

Following these rules and traditions can make a large group renting a big old house a cohesive group, and it’s worked again and again in the many years we’ve returned to Eagles Mere.

Whether it’s a vacation for a family of three or a reunion of three generations, travel insurance can help protect your time together. Seven Corners offers trip protection so you can focus on your time at the market with Mom, quality time at the rental house, and all the great conversations that come with your travels. Contact Seven Corners before your next family vacation.


About the Author

Max Hartshorne has been the editor and publisher of GoNOMAD Travel since 2002. He travels regularly, enjoys publishing new writers, and is proud to be able to truly do exactly what he wanted to do all his life.

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