Thanksgiving Abroad 2019 – Northern Tuscany

After our stay in Florence, it was time to check out some more bucolic Italian environs. We slogged our way through driving rain back to the tram and rode to the Florence airport to pick up our rental car. As usual, we finally got into our car only to discover that although we paid for “in-car WiFi”, the car rental agency was like, “we don’t offer that”. In exchange, they gave us a GPS unit that was only Italian-language and I was mystified on how to actually program it for our destination rather than the car rental offices in Rome. Finally I gave up and just used Google Maps on my phone.

We got on the Autostradale, heading towards Siena. Our Fiat 500 got passed by pretty much every vehicle on the road, thanks to its underpowered engine. We thought it would be cute to drive an Italian car in Italy (and seeing that Ferraris were out of financial reach), we selected the Fiat. A mistake since pretty much everyone else seemed to be driving Audis. After an hour or so, Google Maps indicated we needed to exit the highway and we navigated a series of roundabouts to make our way towards our next lodging. We ascended and the road opened up to sloping farmland on either side. The sun was just breaking through the clouds and painted the landscape a golden hue. It looked exactly like the idealized images we imagine Tuscany to be. Our little Fiat strained to climb the last section into town where we were spending the next two nights – Casole d’Elsa.

Casole d’Elsa is a small Tuscan hill town that was conquered by Siena in 1241 and after centuries of warfare between Siena and Florence, was captured by Florence in 1554. It’s perched up on a hilltop, almost 2200 feet (663 meters) above the countryside. It affords sweeping views of neighboring farms, vineyards, and other hill towns in the distance. My husband booked us into the Torre Dei Serviti, a boutique hotel built into the old city walls. Our room was the Tower Suite, in the ancient tower itself. It was magical, with views of San Gimignano in the distance. The young man working in the hotel was absolutely delightful. Despite my misgivings on my husband’s ability to select hotel rooms, he knocked it out of the park with this one.

Casole d’Elsa is a tiny town. I have no idea what it’s like in the summer; but in the off-season, we were the only non-locals. The first evening, we settled in our room and then took off to explore. The weather, although no longer rainy, had turned incredibly windy. And there is no wind like the wind that whips through an Italian hill town. I was grateful for the scarf I had purchased in Florence but was severely regretting not purchasing gloves as well. The tiny streets of the old town were adorable, charming even (and I don’t use that word lightly). There were hand-painted tiles all along one alleyway that we dubbed the cutest street we had ever seen.

Most of the restaurants and shops were closed for the season but we did see one option for dinner that evening. We went back to our room to relax for a bit. Ironically, the same type of bug that bit me (twice!) in Charlottetown, Prince Edward Island last summer was in our Italian room. Remembering the incredibly itchy bite it gave me, I opted to not liberate this one. Naturally my husband was in the shower and unable to dispatch it himself, so I had to slay the creepy thing on my own. Consider it payback for the week of itchiness your species-mate gave me…

Later in the evening, we walked back to Caffe Casolani, the restaurant we had spotted previously. Of course, we were the first people to arrive for dinner and the staff seemed rather surprised to find two English-speaking tourists in their midst. We were greeted warmly and seated at a cozy table. We had wine, we had pasta, we had the quintessential Italian comfort-food meal. The dining room filled up and by the time we were paying our check, every table in the place was filled. It was a great experience and let us have a glimpse into what the village life might be like when tourists aren’t overrunning the place.

The next day, we had a rather ambitious plan to tour a few of the neighboring hill towns in the area. We set out along winding country roads towards Volterra, about a 30 minute drive away. SP27 twisted through the countryside, depositing us on SR68 to complete the journey. We passed vineyards with bright yellow autumnal leaves and small farms dotted with stone farmhouses. Towards Volterra, the road climbed in elevation. We parked near one of the old town gates set into ancient city walls and wandered. While the lower town was deserted, the upper town was mobbed with people. It was market day. Every open space in the main square was filled with tents selling every imaginable item. After the seclusion of Casole d’Elsa, the hubbub was quite an assault on the senses. We finally retreated to a terrace where we had amazing views of the surrounding countryside. I feel that I need to return to Volterra when it’s not a market day to try to get a sense of what the town is actually like. But after a couple of hours, we returned to the car and pointed the Fiat towards our next destination – San Gimignano.

The route I selected took us through the Riserva Naturale di Castelvecchio. What a gorgeous drive! As we approached San Gimignano itself, there was a spectacular view of the town and its towers. About 40 minutes after leaving Volterra, we had parked and were on our way through one of the gates in the city walls.

San Gimignano is a UNESCO World Heritage Site, famous for its medieval towers. The towers were built as a symbol of a family’s wealth and power. At the peak, there were 72 of these skyscrapers; although only 14 have survived to present times. I have to confess that San Gimignano totally charmed me. Maybe it was the blue skies. Maybe it was the total absence of crowds. Maybe it was Christmas decorations that lined the squares and main streets of the town. Whatever it was, I was under its spell. We ate pizza for the first time in Italy. We had more gelato. We wandered and took a thousand photos that couldn’t quite capture the essence of the town. I ended up dithering around in a leather shop where the sales clerk took the time to explain how to spot the differences between “hand-made by machine” and “hand-stitched” leather bags. After I agonized over spending the money on a “hand-stitched” bag that I loved but couldn’t justify, my husband sent me out into the street while he purchased the bag for me.

Thoroughly charmed by San Gimignano, I was sad to get back into the car. But we had one more town we wanted to try to see before the sun set – Monteriggioni. It was a 30 minute drive, mostly on the Autostradale. As we exited the freeway, we could see the hill top fort practically right next to the road. We drove up to a car park right outside the city gates and headed in to quickly explore before it grew dark. The town is tiny, so tiny – tinier than even Casole d’Elsa. We ended up walking a circuit on the outside of the city walls where the golden sunset light made for some amazing photos. We grabbed a spot in the small piazza and had wine and these addicting black truffle and sea salt potato chips (crisps for you English). The combination was an odd but effective pairing. Sadly the gelato shop in town was closed for the season.

We made our way back to our hotel in the dark, no small feat given the isolated location. The hubster was exhausted and I feared that he was coming down with a virus. He took a nap while I read and a few hours later, he announced that he was in no shape for dinner. I headed into the cold night air to track down some snacks instead so both of us could eat a light dinner. The next morning, I ended up eating breakfast in the hotel alone while the hubby got some more sleep before we had to pack up for our next destination. But first, we stopped off to explore Siena.

Siena and Florence have a rivalry that spawned bloody conflict throughout centuries. I’ve heard that you must take sides – either you love Siena and dislike Florence or vice versa. Honestly, both cities are lovely. I’ve also heard that in the summer, Siena can be just as overwhelmed with selfie-stick-toting tourists as Florence; but we were fortunate that our luck with the off-season crowds held.

We wandered for a few hours before finding a tiny restaurant for lunch and then plugged the coordinates for our next lodging into Google Maps. We bid northern Tuscany arrivederci and headed south on the Autostradale towards our next stop…