Memories of Tuscany: 28 People, 4 Generations, Ages 1–82

May 27, 2020 Updated: May 31, 2020

Last summer, my daughter, my dad, my grandmother and I all saw olive trees for the first time. We walked through the grove next to our villa in the evening light, falling in love with the views of Tuscany, Italy, like so many had before us. “It’s the most romantic country,” I was told over and over by friends before I visited. “You are going to love the evening light against the rolling hills.”

Our villa was tucked up into the hills of Sansepolcro, Italy, at the end of a 20-minute drive on a dirt road filled with crevices that resembled craters more than potholes, past fields of sheep grazing, of sunflowers with their faces stretched to the sun. My mom had found a villa that could hold 28 of us, the number to which my extended family had grown. We stretched across four generations, ranging from my 1-year-old niece to my grandmother, now a great-grandmother of seven. Everyone came: my aunts, uncles, cousins, and their children, from all across the globe, for a week of being together and enjoying one another. 

sansepolcro street
Old historic alley in the medieval town of Sansepolcro, Tuscany. (Poludziber/Shutterstock)

It’s a little more complicated to arrange a vacation when you are trying to accommodate virtually every season of life. Within our group we had single adults, married adults without children, parents with small children, empty nesters, and my grandmother. We knew that, for many of us, experiencing the beautiful region of Tuscany would be a once-in-a-lifetime opportunity. We encouraged everyone to do their own thing and see Italy the way they wanted to see it. 

The medieval city of Siena, Italy. (JeniFoto/Shutterstock)

But, it turned out, the way we wanted to see it was together. 

We visited a few towns around us: Anghiari, a walled medieval city built into a steep hill. We admired the incredible flower displays in windows and pots, drank espresso at a cafe, and enjoyed pizza on a piazza for lunch while the toddlers ran free for a while. We drove our caravan of cars to stunning Siena. We walked through the large square where the famed horse race takes place, and a few of the more active among us hiked to the top of the Tower of Mangia, which looms 335 feet over the city. And of course we spent a few mornings in the town of Sansepolcro, where we saw the “The Resurrection,” a famous painting by Piero della Francesca. 

"The Resurrection" by Piero della Francesca
“The Resurrection” by Piero della Francesca, circa 1460. (Public domain)

As interesting and enjoyable as these outings were, the favorite part of the day for everyone came in the afternoon. After retreating indoors from the 100-degree heat for a siesta, we’d begin to come out, one by one, to the villa’s pool, in the late afternoon. There we could lounge on the lawn chairs overlooking the olive grove. My daughter used floaties for the first time in that pool, and I still remember the way she screamed with glee as my dad guided her around the water. My brother and cousin raced across the pool in inflatable tubes. My grandmother didn’t swim, but sat under a shade tree where she could read her book and watch the ruckus unfold. 

The village of Anghiari is known for “The Battle of Anghiari,” painted by Leonardo Da Vinci. (AdryPhoto1/Shutterstock)

In the evenings, when we were changed and dry and the air had cooled off, we ate at one long outdoor table, all 28 of us. A different family cooked every night, and was sure to have enough wine and cheese for everyone. We would sit around the dinner table late into the night, long after the last bite of food was gone, after the fireflies had come out and small children had finally gone to sleep. We would talk in a way that was unhurried, lingering. That week, we were given the gift of time together, experiencing a place that was new to all of us, but with people who were loved and familiar. 

I hear a lot of reasons why a certain stage of life prevents people from traveling. When you’re young, it’s expensive. When you have small children, it’s frustrating. When you’re older, it’s scary to be away from home. I don’t want to minimize any of the reasons that prevent people from traveling. I want to highlight the joy that it is when we step out of our comfort zone and make the decision to travel, even when it is inconvenient. To be in a new place with my entire family, which stretched from age 1 to age 82, was an incredible experience. Travel, I think, is beneficial for every age. All of us were brought together over one shared experience. 

Our final night together, we had a chef come in and cook us pizzas topped with truffled mushrooms, parmesan cheese, roasted vegetables, and cured meat. The food was exquisite. But afterward, we all said the thing that meant the most to us was looking down the table as everyone sat around it. All 28 of us had saved up and planned for this week tucked away at the foot of the Apennine Mountains. All of us wanted to be there, to experience this new thing together. 

The evening light was gorgeous in Tuscany. But what really made it beautiful was watching it by the stone wall, with my daughter, who sat on my grandmother’s lap.

Rachael Dymski is an author, florist, and mom to two little girls. She is currently writing a novel about the German occupation of the Channel Islands and blogs on her website,