Why We Loved 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 50th birthday. We started in Venice, spent a week in Tuscany, and finished in Rome.

Venice was fascinating. Rome was unforgettable.

But Tuscany was my favorite.

Maybe it was the food and wine. Maybe it was the beautiful countryside and hill towns. Or maybe it was simply the pace of life.

Whatever it was, we loved it.

And after a week there, I already knew we’d want to come back.

Pick One Home Base

One of the best decisions we made was staying in Cortona for the entire week.

Instead of packing up every few days, we unpacked once and took day trips throughout the region. It made everything feel easier, and I loved coming back to the same town each evening.

Our three-story flat, tucked inside Cortona’s city walls, became our home away from home thanks to a stay my husband won through a charity auction.

If you’ve watched Under the Tuscan Sun, you’ve already seen Cortona.

It’s just as charming in person.

Narrow stone streets wind through town, small piazzas pop up around corners, and restaurants and shops spill onto the sidewalks. There were plenty of visitors during the day, but Cortona still felt like a real town rather than a tourist attraction.

That’s what we loved about it.

Don’t Overplan Your Evenings

Our mornings usually started with cappuccinos and croissants at a neighborhood café before we headed out for the day.

We’d visit a hill town, stop at a winery, explore the countryside, or make our way toward Siena.

Then we’d come back to Cortona in the evening, park the car, and walk.

Sometimes we’d stop for a glass of wine before dinner. Other nights we’d browse the shops or sit in the piazza for a while.

We didn’t need an activity planned for every hour.

Some of my favorite memories were simply those evenings in town.

So if you’re planning a trip to Tuscany, I’d leave some empty space on the calendar. You’ll be glad you did.

Some of Our Best Meals Weren’t Planned

On our first night in Cortona, we made the rookie mistake of not having dinner reservations.

After a long travel day, we were tired and hungry and quickly learned that “we’ll just find something” isn’t always the best strategy in Italy.

Eventually, we wandered into a small restaurant with a simple sign outside that said Pizzeria.

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

The food was wonderful, but Tony was the real reason we kept going back.

From the moment we sat down, he encouraged us to practice our Italian. His patience was impressive, especially considering my Southern accent wasn’t exactly helping.

Night after night, locals filled the restaurant. The priest from the nearby church had his own table and regularly stopped in for dinner and wine.

Most evenings, we were the only people who didn’t speak Italian.

By the end of our meal, Tony had us attempting an elaborate limoncello pouring ritual that looked much easier when he did it.

Naturally, we went back on our final night in Tuscany.

It’s a good reminder to make reservations when you need them, especially during busy seasons, but don’t be afraid to try a place simply because you happen to walk past it.

Sometimes those turn into the meals you talk about when you get home.

Take Some Day Trips

One of my favorite things about staying in Cortona was being able to explore several different towns without constantly changing hotels.

Montepulciano

Montepulciano quickly became one of our favorite day trips.

It’s perched high above the countryside and is filled with winding streets, wine shops, and beautiful views.

We visited De’ Ricci for a wine tasting in their centuries-old underground cellars. The combination of the history, the wine, and the setting made it one of my favorite stops.

Montalcino

Montalcino has a different feel.

The fortress overlooking the countryside is worth seeing, but we also enjoyed simply walking around town, browsing the shops, and taking in the views.

Val d’Orcia and Pienza

This is the Tuscany you probably picture when you think about the region.

Rolling hills. Cypress trees. Golden fields. Stone farmhouses.

The drive through Val d’Orcia was beautiful, and we pulled over more than once because we didn’t want to drive past a view without stopping. We also made time to walk down to the iconic photo spot, from Gladiator, where Russell Crowe walks through the field towards his family home.

Sometimes you just have to pull over. Take your time. Explore.

Make Time for the Wineries

You don’t have to be a wine expert to enjoy visiting wineries in Tuscany.

One afternoon we had a tasting near Siena, and the whole experience felt wonderfully unhurried. We talked, tasted, and stayed longer than we’d planned.

Another day, we spotted a winery while driving through the countryside and decided to turn in without a reservation.

A little while later, we were sitting outside with a glass of wine overlooking the Tuscan hills.

That afternoon ended up being one of my favorites.

Back in Cortona, we also wandered into a local wine shop owned by the Ercolani family. A quick stop turned into an evening of conversation, wine tasting, and recommendations.

We ended up having a case of wine shipped home.

I’d call that a successful shopping trip.

Give Florence a Day

If your schedule allows, I’d set aside a day for Florence.

It’s an easy train ride from Cortona and gives you a completely different experience from the smaller hill towns.

We visited the Duomo, wandered through museums, explored side streets, and ate very well.

I also loved discovering Florence’s historic wine windows tucked into buildings throughout the city. Finding them became a little treasure hunt as we walked around.

And yes, the food lived up to the hype.

Fresh pasta.

Florentine steak.

Gelato.

No complaints.

A Few Practical Notes

A few things I’d keep in mind if you’re planning a trip:

• Consider one home base. We loved unpacking once and taking day trips from Cortona.
• Rent a car. If you want to explore the countryside and smaller towns, having a car gives you much more flexibility.
• Make dinner reservations. Especially during busy travel seasons. We learned that one the hard way.
• Leave some unplanned time. Some of our favorite experiences happened when we weren’t trying to get somewhere.
• Don’t skip the smaller towns. Florence and Rome were wonderful, but the hill towns were a big part of what made Tuscany special for us.

Why We’ll Go Back

When I think about Tuscany, I remember the cappuccinos in the square, the evenings walking through Cortona, the long dinners, and the interesting people we met along the way.

It wasn’t one particular sight or experience.

It was all of it together.

We loved the food. We loved the wine. We loved the towns. And we especially loved having enough time to enjoy them without rushing from one thing to the next.

So yes, we’ll be back.

I’m already looking forward to it.