The Rolling Hills of Tuscany

“That is why many of us travel: not in search of answers, but in search of better questions.” — Pico Iyer

Tuscany is one of the only places that has lived up to the expectations Jeff and I had. Every picture you see of Tuscany, I am here to tell you, is accurate. The landscapes go on forever and the villages are so quaint, they look like they haven’t been touched by time.


We stayed about 8km south of Florence in a small, blink-of-an-eye town called San Donato. In the center of the medieval village is a watchtower originally built in 1146 that has been converted into a home. Thanks to AirBNB, we had three lovely days in this villa.

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It was originally owned by the Bardi family. They dominated the region before the Medici family took over, but it was later traded, bought, and given to many people including an orphanage. But in the 1800s, the Carpi family bought it and turned it back into a personal home. During WWII, Rodolfo Carpi used the villa to throw soirees for Fascists all the while hiding allied soldiers in the tower. The Carpi lineage owns it to this day.

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As soon as you walk in, you’re steeped in history. At the entrance, there are two massive bookcases that house hundreds of tomes dating back to the 1800s and early 1900s. We both had never been so close to such history, and here we were holding it in our hands. We could not help but feel humbled in the historic walls of this home.

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While our time was short in Tuscany, we took every advantage we could to see as much as possible. Our first night in the region, we spent in Montalcino. I had been reading Vanilla Beans and Brodo by Isabella Dusi all about the small village, and I wanted to see the gorgeous city she had described so completely.

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Famous for their ancient walls that has saved them from massive wars against the Spanish, French, and fellow Italians, and their Brunello wine, Montalcino is situated on the south end of Tuscany near the city of Siena. Originally established in Etruscan times, the small village is the home of some really incredible history. The Fortress of Montalcino still stands from the 13th century and they continue to annually have archery festivals celebrating the long-loved history of the town.

We pulled in to the city and parked on the outskirts. Something to note about the small villages: most of them do not allow car traffic within the city itself. Parking can only be found along the perimeter.

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We enjoyed a late pranzo before we took a short tour of the city. While walking around, we stumbled upon San Pietro Cathedral. We walked in because we have a fascination with churches, but more to my interest, I saw people hand-restoring the frescos on the walls. I was stunned. It wasn’t done in a lab or protected environment off-site. They were standing on scaffolding and repainting the delicate images right there for us to observe. What I learned is the neighborhood of Pianello has been given the opportunity to buy their church from the diocese, but it is need of significant repair. In order to purchase it and own it out-right, they have to restore it completely. It was a lovely sentiment to see a village taking care of their own history.

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We didn’t stay long enough in Montalcino to really soak in every nook and corner. But we had a date set for the Sant’Antimo Abbey just a seven minute drive further south of Montalcino. At various times during the day, the monks of the abbey chant songs of their faith. In planning this leg, I mistakenly read their line up, so we missed the last performance by 15 minutes. It was disappointing to not see this famous concert, but the abbey itself was quite stunning.


While the exact date of construction is unknown, the foundation dates back to the times of Charlemagne. There are some rumors that Charlemagne founded the church originally, but these have never been founded. But at the very least, the abbey is documented as early as 813 in a land grant document which still exists in the archives of Siena.

Its exterior is more beautiful to the eye than the inside, yes, but the inside has a very classically plain and simple church feel. The hard stone keeps the air cool, even in the heat of August. But outside, the structure is idyllic with gardens that surround it full of olive trees and lavender bushes. The monks even sell satchels of lavender to locals and tourists alike.


We left Sant’Antimo and headed back to our tiny town. There isn’t much in San Donato except a small junk shop that also carried fruit and veggies and a small bodega where we got basic groceries for our breakfast. But another one of the small shops was the Gusto Di Vino: a small craft beer and wine shop where we picked up a lovely bottle of prosecco to enjoy with some figs, cheese, honey and the Tuscan sunset.

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* * * * *

The next morning, we piled in our tiny SmartCar (a vehicle I wouldn’t wish on my worst enemy) and headed toward Lucca. A little farther north of Pisa and Florence, Lucca is another medieval town that has gorgeous fortress walls that surround the city center. The walls are incredibly high and even have trees growing on top! I have never seen such a thing and marveled at how nature always finds a way.

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We didn’t know much about the town except for the many, many churches housed in the city. We first walked toward St. Martino Cathedral or Lucca Cathedral. Standing proudly in the city, the white-washed walls and tall tower give an imposing image. Inside the cathedral, there is a small golden cage with a crucifix known as the Shrine of the Sacred Face of Lucca or Holy Face of Lucca. Legend says it was sculpted by Nicodemus who assisted Joseph of Arimathea in burying Christ in his stone tomb. Of course, what is on display is not the original sculpture, which is why the tale is a legend. The current statue was created in the 13th century (so, no big deal…).


After St. Martino, we found ourselves inside San Michele in Forno and then St. Peter. San Michele is a much grander church and the major attraction to Lucca. We did have to pay a couple euros to go inside, but it certainly was a beautiful church with incredibly artful architecture. Originally built as early as 795 and rebuilt in 1070 by Pope Alexander II, the gorgeous church is one of the biggest “sacred destinations” in all of Tuscany. St. Peter was not nearly as impressive as the two other buildings, but being further away from the city center, it did give a sense of peace the others could not give.


* * * * *

You can’t holiday in the Tuscan region and not book a wine tour. I wrote briefly about our wine tour with Barone Ricasoli in the Grapes and Beans entry, but I did promise a little more history from this incredible castle nestled in the rolling hills.

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Castello di Brolio was originally built in the 1100s but sustained incredible damage during the 1472 war between the Florentine and Sienese armies. The Medici family rebuilt the glorious castle, but they allowed the Ricasoli family to retain the title of the land and home. The castle has been in the same family for more than 800 years with now three members in the family still residing in the walls. In the picture below, you can see the subtle difference in the color of stone. The darker stone was the original structure from the 1100s. The lighter color is what had to be rebuilt after that 1472 war.IMG_2963

The classic wine tour was from 10:30-12:30 and was only €25 per person. This was a bargain for all of the history and wine we got to taste. Our guide, Melanie, started us in a small chapel built on the grounds that houses the deceased family tree beginning in the 1800s. It was absolutely gorgeous and unnerving to see so many family members in the same place. It was also pretty amazing to be inside something so sacred and private to such a small and famous family.


Benito Ricasoli was the man responsible for creating the Chianti formula in the 1800s. To qualify for Chianti Classico, there must be 80% Sangiovese grapes. Regular Chianti must have as “little” as 70% to qualify. The tour ended with us going through their factory. They use gravity to crush their grapes using a very natural process to get their wine. They use hand-pickers only and have very specific formulas for their soil that they take much pride in.

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Aside from the glorious views from the castle, what struck me was the south facade. In the courtyard, there is a tree with a large hole in the middle. During WWII, a bomb barreled through the tree, but the tree continues to stand. The Ricasoli family never uprooted it as a symbol for survival. Also on the walls of the castle are war wounds. Deep scratches are etched into the building from shrapnel. When the Germans lost and the Fascists had to leave the castle, the General in charge was ordered to bomb it. Lucky for us, and the world, he only bombed the outside of it, preserving the structure.


To read more about the wine tasting itself, click here.

* * * * *

After buying a couple bottles of precious wine, we found ourselves in San Gimignano, a small town to the south west of Florence famous for retaining their fourteen medieval towers through the myriad of wars. They were never bombed during WWII, so finally, we can see how the town was meant to be preserved. From a distance, the town looks like a mirage of towers and stone against the lush green fields and trees. It’s quite striking to see it so isolated and untouched.

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We parked, again, on the outside of the city and stumbled along the steep inclines and declines of the village. Since it was toward the end of the day, Jeff and I decided we would amble around and strictly take in the sites. We had no agenda here which gave us the freedom to just look up. The towers were really beautiful, and while we didn’t climb any, we marveled at the landscape and the historic charm the small village retained–despite the flood of tourists and travelers buying gifts, gelato, and wine.

We walked hand in hand through the small alleyways and reflected on what these city walls must have seen all the while realizing how young America is.

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I firmly believe, out of all the destinations we have traveled, Tuscany will be one of the first we return to in our future. It’s exactly what we hoped and dreamed it would be.

On our last night, we sat on the terrace with our bottle of wine and soaked in the smell of impending rain. With thunder and lightning in the distance we huddled in our blankets and looked out on the gorgeous landscape.

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Stay tuned in the coming weeks for The Vatican and Venice!

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