I Vacationed in Italy With 18 Family Members

Here's how it all turned out.

By

Janie Emaus

 
Published October 23, 2025
photo collage of photos of italy vacation with 18 people
AARP (Courtesy Janie Emaus, 2; Getty Images, 3; Stocksy)

Pizza, pasta, wine, water park? When I envisioned our family trip to Italy, sliding down winding tubes at a water park with children was not on my itinerary. I saw myself drinking wine and toasting my sister’s 75th birthday. In reality, this vacation gave me more than I could ever have imagined: peace and reconnecting with my intergenerational family, ranging in age from four to 77.

The trip had been planned for over a year. Finding a kid-friendly villa that slept 18 people, had a pool and was in a good location took research and due diligence. After much correspondence, my sister booked a villa in Ostuni, located in the Puglia region of Italy, which is famous for its olive oil.

Although we arrived late at night, tired and hungry from 20 hours of travel, no one could deny the magic in the air.

Family members arrived from Thailand, Denver, Ohio and California. The villa had four kitchens, six bathrooms, seven bedrooms, a pool and an amazing rooftop. All this space made it easy for each family member to have some alone time, with the rooftop and pool becoming central gathering locations.

By the second morning, we fell into an easy rhythm. Several unspoken rules enhanced the peaceful, easy feeling of being in a very diverse group.

Respect Each Other’s Personal Space, Both Physical and Mental.

Morning hours were spent with people engaging in their preferred activities. We were careful not to disturb each other’s solitude. The pool was a bit short, but adequate for lap swimming. The roads winding through the olive trees made a perfect setting for walking and running. And the many quiet areas on the property provided ample room for practicing yoga.

The first person in the kitchen made several pots of coffee. Everyone was on their own for breakfast. Usually by mid-morning, the kitchen was alive with a blend of voices, from toddlers to septuagenarians, echoing off the walls.

Make Time Together & Time Apart

As much as we all love each other, it’s impossible for this number of people to travel in a pack. Arrangements were made for a few girls' nights out in which the men stayed with the kids. On several occasions, the grandparents babysat while the young couples went to dinner. When all of us went out to eat together, we sat at separate tables in the same restaurant, which made it cozier and easier for conversation. We often split into small groups and ventured out to explore in different directions, to the must-see sites.

Plan Daily Activities for Every Age

Each morning, the 40-something women, with the help of local travel guides, arranged beach outings, hands-on activities and dining options, while my sister and I were still begging the Internet to respond to our tourist questions. The kids should also have a say in the planning, but ours would have chosen the beach almost every day. Introducing them to Italian culture and way of life was an important factor in our trip.

We drove to the neighboring towns, one of them Alberobello, home of the Trulli, a small dwelling reminiscent of a Hobbit house. This village enchanted even the youngest among us. Olive oil tasting left our palates wanting more. Pasta-making came easily for my great niece, who let me know I was better at consuming the various noodles than creating them.

One of the highlights for those of us with sea legs was our boat tour through the caves of Polignano a Mare. The lights and colors inside these ancient caves captivated everyone’s attention. The cruise ended with a swim in the Adriatic Sea. And let’s not forget our afternoon Aperol Spritz, a necessary heat reliever for the adults and then gelato, an icy and delicious traditional Italian dessert.

Arrange for Gathering Together

Afternoons were spent around the pool, a relief from the blaring heat. While the kids’ giggles resounded, some of us (yes, the older ones) took much-needed siestas. After all, how can you not engage in all things Italian when in Italy?

In the evenings, we gathered on the rooftop for drinks and appetizers, family games and enjoying shows performed by the children. As the sun moved toward the horizon, spreading shades of pink across the sky, we chatted about the day’s activities and caught up with each other’s lives, leaving judgments on the doorstep.

The beauty of our surroundings and our love for each other created an atmosphere of respect. We managed to survive the days with only a few disagreements, mostly over the confusing GPS system installed in the car I shared with my sister. Meanwhile, our daughters, nieces and sons would speed off, leaving us lost among the twisting, tiny streets more suitable for a ride at Disneyland than an actual car.

But getting lost in Italy, on land that has been inhabited since the Stone Age, simply added another layer to this amazing vacation.

The days continued with amazement at the water park. Watching from my lounge chair reminded me of the joys of being a kid, the responsibilities of being a young mom, and the benefits of now being the grandmother who gets to relax and enjoy her family.

No doubt about it, this trip left all of us with memories that will last a lifetime.

Arrivederci!

Would you ever want to go on a trip to somewhere like Italy with extended family? Let us know in the comments below.

Janie Emaus is the author of the blended holiday picture books, Latkes for Santa Claus, a finalist in the 2022 International Book Awards, and Easter Eggs & Matzo Balls. Her third picture book, Mrs. Claus’s Noodle Kugel, will be released in September 2026. She is also the author of the novels The Advice Columnist and The Time Traveling Matchmaker. Her essays, stories and articles have been published in numerous magazines, anthologies and websites. To learn more about Janie, visit janieemaus.com.