See You Again Soon, Tuscany

Have you ever visited a place and immediately known you’ll be back?

For us, that place is Tuscany.

A few months ago, we traveled to Italy with our adult children to celebrate my big 5-0 birthday. Spending your 50th birthday in Italy is definitely not terrible… and softened the blow a bit. In all seriousness, it was just an incredible trip.

We started in Venice (which deserves its own post someday), spent six nights and seven days in Tuscany, and then finished our trip in Rome. Since it was our first time in Italy and we’re both history lovers, Venice and Rome were the perfect bookends to the trip. But tucked right in the middle was a week in Tuscany that completely stole our hearts.

We based ourselves in Cortona, a charming hilltop town that happened to be the result of my husband winning a stay there through a charity auction. We stayed in a three-story flat just inside the city walls, and it ended up being the perfect home base.

If you’ve ever seen Under the Tuscan Sun, you’ve already seen Cortona. The movie was filmed there, and honestly, it looks just like it does on screen.

The town itself is perched high on a hill and filled with restaurants, shops, and winding streets. While there were certainly visitors around, it still felt very local. We traveled in the fall, so tourism had slowed down some, which may have helped. Either way, it never felt overly touristy.

What we loved most was the rhythm of life there.

We could spend the day exploring, then come back, park the car, and simply enjoy the evening. We’d grab a glass of wine before dinner, order an appetizer, and wander through town. In the mornings, we’d head to a local café for cappuccinos and croissants.

Most places we visited weren’t Americanized. Menus were in Italian, and we did our best to order in Italian as well. I’m sure my Southern accent didn’t do the language any favors, but we gave it our best shot.

Of course, some of our favorite memories weren’t the things we planned at all.

Our very first night in Cortona, we made the rookie mistake of not having dinner reservations. We were hungry, tired from traveling, and getting a little desperate to find somewhere to eat. We ended up walking into a small, unassuming place that simply had “Pizzeria” on the outside.

It turned out to be one of our favorite spots of the entire trip.

Yes, the pizza was fantastic, but they also served wonderful pasta and other traditional dishes. What really made the experience, though, was Tony.

From the moment we walked in, he encouraged us to practice our Italian. He would gently challenge us to order in Italian instead of English, and while I’m sure my Southern accent wasn’t helping matters, he was always patient and encouraging.

The restaurant felt incredibly local. In fact, the priest from the local Catholic church had his own table and would come in during the evenings with his jug of wine. Most nights, I felt like we were the only people in the restaurant who didn’t speak Italian.

By the end of dinner, Tony had us attempting to pour our own limoncello in a very dramatic and elaborate fashion. It was one of those experiences that you can’t plan for and probably couldn’t recreate if you tried.

We loved it so much that we returned for dinner on our last night in Tuscany.

One of our favorite day trips was to Montepulciano. If you’ve seen photos of Tuscany’s famous hill towns, chances are you’ve seen Montepulciano. The town sits high on a ridge with beautiful views of the surrounding countryside, and it’s full of winding streets, shops, and little corners that make you want to slow down and explore.

While we were there, we did a wine tasting at De’ Ricci, and it ended up being one of the highlights of our trip. The winery has underground wine cellars that date back to the 1100s, and the history alone is worth the visit. We were fortunate enough to have the owner and winemaker lead our tour, which made the experience even more memorable.

Another favorite day trip was Montalcino. Like many Tuscan towns, it’s perched high on a hill and surrounded by incredible views. We spent time exploring the massive fortress that overlooks the countryside and wandering through town. It’s easy to see why people fall in love with these medieval hill towns.

We also spent several hours at a small winery outside Siena, enjoying a long, leisurely tasting and learning more about the winemaking process. It was another reminder that Tuscany really knows how to slow you down in the best possible way.

If you’ve ever watched Gladiator, you might recognize the rolling countryside around Pienza in the Val d’Orcia region. We made a stop there as well and visited the area where Russell Crowe’s character walks through the fields toward his home. It was fun to see in person, but honestly, simply driving through that part of Tuscany was worth the trip. The scenery is every bit as beautiful as you’ve imagined.

One thing we loved about Tuscany was that you didn’t have to have every minute planned. Some of our favorite moments happened simply because we pulled off the road to explore something that looked interesting.

One afternoon while driving through the countryside, we spotted a winery and decided to stop. A little while later, we were sitting outside enjoying a glass of wine with some of the most beautiful views imaginable. No reservations. No schedule. Just one of those spontaneous moments that ended up becoming a favorite memory.

Back in Cortona, we also stumbled into a wine shop owned by the local winemaker Ercolani. We weren’t looking for anything in particular, but we ended up spending a wonderful evening there.

The woman working in the shop was absolutely delightful and kept pouring tasting after tasting while sharing stories and recommendations. Before we left, we had purchased a case of wine to ship home to the United States. It felt less like shopping and more like spending time with a friend who happened to know a lot about wine.

We also spent a day in Florence. Rather than driving, we took the train from the station at the bottom of the hill below Cortona. It was incredibly convenient and made for an easy day trip.

Florence was everything we hoped it would be. We explored museums, visited the Duomo, wandered through the city, and of course enjoyed some great food. One thing we thought was especially fun was spotting the wine windows throughout the city. These tiny windows built into centuries-old buildings were originally used to sell wine directly to customers, and some still do today. It’s such a small detail, but it’s exactly the kind of thing that makes Italy feel connected to its history in a way that few places do.

And then there was the food.

One evening in Florence, we had a traditional Florentine steak that was every bit as good as everyone says. We also enjoyed a meal where fresh pasta was prepared right at our table, which was both delicious and entertaining to watch.

But when I think back on Tuscany, it isn’t necessarily the wineries or the sightseeing that stand out the most.

It’s the feeling.

Life simply seemed slower there.

The food was fresh. The wine was fantastic. Not once did we wake up feeling bad from anything we’d eaten. And in all honesty, we had our fair share of wine. There was a simplicity to everyday life that felt refreshing.

Each morning, we’d see many of the same locals gathering for coffee in the square before heading off to work. Then in the evenings, we’d often see some of those same people enjoying a glass of wine and visiting with friends.

There was a sense of community that was hard to miss.

Between the beautiful countryside, the gardens, the food, the wine, and the slower pace of life, Tuscany felt authentic in a way that’s increasingly hard to find.

It inspired me to try to create those spaces and moments here. From my small kitchen garden to cooking my own pasta, I left inspired.

It was the perfect place to celebrate turning 50.

And if there’s one thing I know for certain, it’s that we’ll be back.