Hill Towns of Tuscany

See our gallery of photos tagged with “tuscany”.

I’m sure I’m not the only one who read Under the Tuscan Sun by Frances Mayes and decided that I must visit Tuscany one day. But I have clear memories of reading that book during my first or second year in DC and dreaming of sitting at a table in the hills of Tuscany with fresh tomatoes, olives and wine. Now, almost ten years later, I am lucky enough to find myself exploring the hill towns with Dan in our little rented Fiat. Although we didn’t make it to Cortona, the town that Frances Mayes made her home, we covered a lot of ground and got a great taste of the good life in Tuscany.

We picked up the rental car in Siena on Wednesday, along with a detailed road map, and we headed for the hills. The road map did not end up being necessary, however, thanks to Dan’s trusty Nokia N810, which he enabled with a one-week free trial of GPS-based navigational software right before we left Siena. The GPS proved to be hugely helpful in finding our way between the many small towns and helping to determine driving time, etc. We’d definitely recommend it. Our car was great also. It was a Fiat that handled really well and was shockingly fuel efficient. It took diesel gas and we only used three-quarters of a tank throughout three full days of driving.

Our first stop was San Gimignano, which is a very picturesque town that is dominated by its many medieval towers. It was fairly crowded here with other sightseers, but we thoroughly enjoyed our lunch in the main square, as well as some fabulous gelato from a place that won the 2006 World Gelato Championship (or something like that). On our way out of town, we drove up a gravel road that provided us with postcard-perfect views of San Gimignano — one of the many examples of why it is great to have your own wheels in this region. Next we headed for Volterra, which shares a name with one of our favorite restaurants in Seattle that was also the scene of our third date. Volterra would be our home for our first night in Tuscany and we quickly fell in love with its beautiful views and authentic charm. As with all of these towns, you drive uphill to get there and are rewarded with sweeping views of the surrounding countryside. One of the highlights of our stay in Volterra was a pre-dinner visit to a wine bar called La Vena di Vino, where we shared a wine tasting sampler that included Chianti, Brunello di Montalcino and a Super Tuscan. They were all great wines, but the experience was made more memorable by our very charismatic hosts Bruno and Lucio. They were extremely friendly and welcoming and Lucio — apparently famous in Volterra for his karaoke singing — treated us to an a capella rendition of Frank Sinatra’s ‘My Way.’ (This wine bar is also the proud home of the karaoke dentist chair featured in Round III of What Is It??)


After one night in Volterra, we made our way to the town of Castelnuovo Berardenga. This town was not featured in any of our guidebooks, but it was close in proximity to a restaurant that we were targeting for Friday night, so we decided to visit for lunch and see if there were any rooms available. This place definitely felt a bit off of the beaten track, in a very welcome way. We had to use our limited Italian vocabulary to communicate and the population featured more locals than tourists. We ate some lunch in the main square and then walked down to a bed & breakfast that we had passed earlier. At Il Pozzo della Citerna, we met Rosa, a delightful elderly woman who spoke not a word of English. Although we couldn’t communicate with each other, she helped us call her daughter, who said that all of their rooms were full but she could help us find a room elsewhere if we would just call back a bit later in the afternoon. That was our first introduction to Sara, who would end up being a huge help to us and an inspirational example of the “kindness of strangers.”


Following our visit to Castelnuovo, we drove south through a region called Crete-Senesi. This is a very hilly area that provides some striking views of Tuscany — the kind that look like what you see on postcards or calendars with a line of pointy cypress trees heading uphill to a lone farmhouse. This was a very beautiful area. Our destination that afternoon was Montalcino, where we would spend our second night in Tuscany. This is yet another lovely hill town that is surrounded by vineyards, with all of the stores offering its famous Brunello di Montalcino wines. We quickly found a place to stay in the main town that was situated above a bakery that smelled absolutely amazing. One thing that we loved about Montalcino was how authentic it felt and how easy it was for us to feel a part of the community. We went out for a walk in the evening and were impressed by how many locals were out strolling together. And they all said Buena Sera to us as we crossed paths. This is one thing that I love about Italy. You see these groups of older women or men walking together arm-in-arm or sitting on benches together in the evenings just chatting. We both love the feeling of community that this provides and wish that we had a bit more of this back in the States. Anyway, we had a simple (but delicious as always in Italy) pasta dinner, sat out in the main square to read the paper, and then went to bed pretty early.

On our final full day of driving, we headed for Pienza in the morning. This town is famous for its Pecorino cheese (which is one of Dan’s favorites) and all of the shops are chock full of wheels of different types of Pecorino. We bought “a taste” of Pecorino from one of the shops, which was quite delicious, before hopping back in the car to drive south to Civita di Bagnoregio. This is the place that Rick Steves calls “the ultimate” Tuscan hill town. Although it was a bit of a drive, we are so glad that we made the trek. Civita and Bagnoregio are two different towns that were historically connected by a land bridge. Now it is a man-made bridge that you use to traverse between the two towns. Civita is tiny and quite literally perched on top of a hill. Bagnoregio is larger and provides breath-taking views over to Civita. We did make the climb up into Civita, but both agreed that the highlight of the visit was viewing the town from Bagnoregio.



We spent our final night back in Castelnuovo, where we had arranged to meet Sara at 5pm in front of her b&b. Now back to the inspirational “kindness of strangers” experience … It turns out that Sara had arranged for us to rent a room from her friend down the street who does not speak any English. So Sara instructs us to bring our car up to the corner, where she will be waiting on her bike, and then she will guide us over to her friend’s place. We can’t believe how nice she is to do this, but Sara does proceed to absolutely fly on her bike the one kilometer down the road to her friend’s place. Here we meet Amelia who does in fact have a very lovely room for us at a very lovely price. So this is where we stayed for our last night in Tuscany: a beautiful, quiet bedroom with doors that opened into a grove of olive trees. Seriously. With a free parking place that only required us to carry our packs about fifty feet. After thanking Sara profusely, she explained that she was happy to help because she would only hope that someone would do the same for her if she were in a place where she didn’t speak the language and was trying to get situated. We made sure to share our contact information so that we can return the favor if she ever finds herself in the U.S.

The town of Castelnuovo was only about 8km from the restaurant that our friends Ben & Elisa had visited a few years ago and for which they had given glowing recommendations. So after several nights of picnic lunches and cheap pasta dinners, this would be our splurge dinner in Italy. 30 Bottega is just off of a very small, quiet road that would have been very hard to find without the GPS. We arrived around 8pm for what proved to be a wonderful and highly memorable meal. We were seated in a covered room that opened onto a garden patio. Our meals were divine and I could write a full post just about what we ate. Since this is already getting really long, I’ll cover the highlights: figs stuffed with goat cheese and wrapped in pancetta, a big ravioli with an egg inside that broke only when you cut into the ravioli, delicious veal for me and three-hour-roasted duck for Dan. It was fantastic. And to complete the experience, right before we started our dessert, a rocking hailstorm came out of nowhere and produced these enormous pieces of hail that were ricocheting off of the metal tables on the veranda and into our covered room. We and all of the other diners had to huddle our tables together and the staff set up umbrellas facing outside to deflect all of the hail. It was quite the sight, but actually kind of fun. After finishing our dessert and waiting for the heavy rain to pass, we drove home with full bellies and quickly fell fast asleep.


3 thoughts on “Hill Towns of Tuscany

  1. I have to say, I’m jealous. The Italian people are so awesome, that I’m sure you’ll have many more positive memories from kind strangers in the future. Makes me wish I were back in Italy, hanging out at some crazy, techno/internet cafe singing karaoke in a converted, internet-enabled dental chair, with some fava beans and a nice Chianti… lucky buggers.

  2. Loving your report on Tuscany! I miss it so much already. I have to say I laughed out loud when you mentioned Frank Sinatra’s “My Way”. They must love it in Italy! When Mike and I were there the song followed us around…we heard it from a street singer in the Cinque Terra, from a restaurant band in Bellagio and on the radio a few other places…”and bad mistakes…I’ve made a few…”

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