Tuscany, Italy

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Our anniversary trip began in the bustling, beautiful city of Florence (click here for that post). From there, we headed to Tuscany’s rolling hills, olive groves, vineyards, castles and hilltop villages.

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Getting there:

We tried to Uber from our VRBO to the airport, but our rides kept getting canceled. THREE TIMES! So, we finally gave up, WALKED to the city center, and hailed a good old-fashioned taxi to the car rental area near the Florence airport. There, we stood in a LONG line to pick up our pre-booked rental car. Eventually, we got the keys to a pretty BEAT-UP car, piled in, and hit the road! First stop: Siena.

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Siena

Siena feels like stepping into the Middle Ages. The medieval streets wind and tilt, and then you stumble across the most magnificent cathedral with carved, intricate marble. The inside is breathtaking too. It’s hard to beleive that this “duomo” was built 1000 years ago! Simply incredible!

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From Siena, we checked into our resort that started as a monastery 1000 years ago! We had an amazing dinner in an ancient wine cellar, surrounded by beautiful stone walls and vaulted ceilings. The cheese plate was divine, the pasta – delicious, and my eggplant parmesan was melt-in-your-mouth amazing!

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In the morning, we enjoyed a leisurely breakfast and cappuccino on the patio, and then set off to discover more of what makes Tuscany so special.

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Castle Meleto: Established 1256

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We toured a castle that was built in the 1200s. It’s hard to wrap your mind around the fact that you are exploring spaces that people have lived and worked in for 800 years. Our tour guide shared with us how they make their wine, honey and olive oil, and then let us taste each one.

My favorite part of the tour was seeing inside a locked room that let to a THEATRE, with the original backdrops from the 1700s still hanging!

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Castello di Brolio

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Our next stop was Castello di Brolio, where we enjoyed lunch at Osteria di Brolio followed by a walk around the castle grounds.

The first stones of Castello di Brolio date back to the early Middle Ages, and the property has belonged to the Ricasoli family since 1141. That’s nearly 900 years of family history! The castle also has an important place in Italian wine history. Baron Bettino Ricasoli helped develop the formula for modern Chianti wine right here in the 1800s.

The castle itself is still privately owned by the Ricasoli family, and the family residence is not open to the public. We were able to explore the stunning grounds, gardens, and chapel.

One detail that really caught my attention was the bullet and artillery damage still visible on the castle walls from World War II. In July 1944, the castle suffered significant damage from the Germans. The castle was ordered to be destroyed by the German officials, but one German officer deliberately disobeyed orders in order to save this magnificent castle!

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Monteriggioni

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Monteriggioni was my favorite ancient village to discover.

It’s a beautiful, tiny village completely encircled by a medieval wall.

Naturally, I had to know how thick that wall really was. So I did what any curious traveler would do: I laid down across the top of it. And remember, this wasn’t built with cranes or machinery. Every stone was laid by hand, between 1213 and 1219, by the Sienese to defend against Florence. Lying there, I tried to imagine the labor involved and what life was like at that time.

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Tuscany: A Beautiful Change of Pace

Between the olive groves, rolling vineyards, golden hills, and centuries-old castles and villages, this part of Tuscany feels incredibly peaceful.

After the noise and busyness of Florence, it was such a lovely change of pace. I loved slowing down, taking in the scenery, exploring the historic villages, and simply enjoying the beauty around us. I’m so glad we carved out a couple of days to experience this part of Italy.

If you love rolling hills, charming historic villages, and a slower, quieter pace of travel, Tuscany belongs on your list!

Thanks for traveling with me! Next stop: the Amalfi Coast!

And in case you missed it: Click here to read all about Florence!

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If you’ve been to Italy, what do you love or not love about it? Where did you go? Leave a comment by clicking the little text box by the title of this post!