Eric sizes up the competition in San Gimignano

We still had another day up in the hills ahead of us and I didn’t really want to continue making the perilous drive back to Florence each evening knowing what I knew about the drivers and the roads. I mentioned before that my friends were all staying at this castle, the Castello di Montegufoni, near the tiny village of Montespertoli, which was about 45 minutes away from Florence. I wasn’t able stay there with them because it was sold out (we think because of a wedding party). But we decided to go ahead and see if I could stay for just one night so I didn’t have to drive back that evening. Marie went to the desk and asked and it turned out that they did have one room for that night only so I jumped on it. I couldn’t give up my hotel room in Florence since I would be returning for another night, but the extra night’s cost was worth the relief from having to drive back again after a long day in the Chianti hills, plus we could all sit and talk that night while enjoying some wine without worrying about driving.

Castello di Montegufoni stairs to my room

The view and pool at Castello di Montegufoni

I needed to hustle up to the castle as it was Saturday and they were closing at noon. As I drove up to the castle through the twisting roads of the Italian countryside I was finally greeted by the 13th-century structure that included a tower and a courtyard surrounded by rooms on three sides. It was still off-season and the citrus trees lining the courtyard were all covered with white sheets, and the restaurant was still closed. But the glory and history of the structure was still easy to feel and the surrounding landscape felt akin to going back in time. I met with the owners in their office to secure my room in what felt like a grand Renaissance dining room from a movie set. I was then led to my room for the night through a series of small arched passageways and finally up a steep staircase with foot-worn granite treads to a large comfortable room. The room was quite a bit larger than what either Mark and Marie or Eric and Patricia were staying in, which I don’t think sat well with them—and it was way more space than I needed—but in any event, we decided it would be where we would enjoy the evening together since it could fit everyone comfortably.

We were to split up for the day. Mark, Marie, and Eric were heading south to go soak in one of the natural pools fed by the many hot springs that pop up all over Tuscany, but both Patricia and I had made faces when we heard this idea earlier, so we decided to hang together that day and go do something else instead.

That something else turned out to be a day trip to Siena, the last city in Tuscany to which I had never been. To our modern eyes, the difference between Florence and Siena seems negligible, but historically these two cities were sworn enemies whose sons spent centuries killing each other trying to dominate the other until finally Siena fell and Florence became the dominant republic of the region. This is why Florence, with the help of the Medici family, is so much larger and has all of the fantastic museums and economic clout. But Siena, I have to say, is the much cooler city because it’s smaller, less touristed, but still has the beautiful rolling hills and medieval architecture. The jewel of the city is the brick plaza known as Piazza del Campo. This is where the The Palio di Siena takes place. The Palio, which is a traditional medieval horse race run twice per year, and pits riders representing seventeen neighborhoods, known as Contrade, against each other, is attended by large crowds, and is widely televised. Imagine the scene: the flags, the riders in colorful uniforms, the rabid neighborhood residents packed into the center of the track cheering for their rider, who race in the tight circle around the plaza beating and kicking each other from horseback. Winning the race is a colorful point of pride for the Sienese neighborhood that wins it, at least for six months. Long tables are set up in each neighborhood out on the streets and the food and wine flow freely. But when no race is being run, which is most of the year, the plaza is more or less a giant brick beach, where people lay about, have picnics, and otherwise soak up the sun and do some serious people watching.

Patricia and I had the best day of the entire trip while we explored the city on foot. We walked along the outer walls and then through the tiny stone streets. She found some things to buy in the shops and I found some wine to buy (surprise!) for that evening. Then we found a great little wine bar where we shared a bottle and some excellent charcuterie before we picked a spot in the Pizza del Campo to join the others to enjoy the beautiful sunshine. We continued exploring the city before happening upon the Santuario Casa di Santa Caterina, which was Saint Catherine's home, now a sanctuary, with art-filled rooms and plazas, a small church, and Catherine's frescoed cell. The large pieces of art seemed to just pull us in from the street and nobody seemed to be stopping us from entering and exploring where we saw even more art, the small chapel, and we caught views of the city. It was an incredible surprise.

Exploring the fortified city walls of Siena

Archways that lead to Piazza del Campo, Siena

Enjoying the sun in Piazza del Campo, Siena

Matt and Patricia having the *best* day in Siena

The sculpted metal gate of the Santuario Casa di Santa Caterina

When we left the castle in the morning we purposely took all of the smallest mountain roads through the vineyards and olive groves, catching the views of the rolling hills of Tuscany and the snow-capped Apennines off in in the distance on our way to Siena. After our long day there, we just wanted to get back as quickly as possible, so we took the new-ish highway between Siena and Florence which only took us about 30 minutes to get back. If only they had this highway 500 years ago perhaps not as much blood would have been spilled between the two cities.

When everyone finally made it back to the castle and showered their hot springs sulfur spew off, we reconvened in my room to share some Chianti wines. They showed us pictures of the hot springs and of them soaking in the white crusty water. Patricia and I winked at each other knowing we had the better day. (I know they are reading these words and will vehemently deny this. They thought Patricia and I were big wusses for not going with them. But hey, nobody wants to see my pasty white big carcass soaking in a sulfur bath, especially me. I’ll take the bottle of Sagrantino di Montefalco at noon and an entire day of intellectually stimulating conversation while roadtripping in Italy with my friend, Patricia, any day.)

The next morning I got up early enough to wander around the castle grounds which were historic and stunning. Later, as we readied to leave, we ran into this very nice man from Texas who was also staying in the castle and we chatted for a while, agreeing that this part of Italy and this castle in particular was a gift to the senses.

Then we headed off to another day of wine tasting, specifically visiting Castello Monsanto, which was a bucket list place for me. Everything about it, the tour, the cellars, the vineyards, and the ancient castle were about as picture-perfect as I could have imagined it might be. I worked on our guide the whole time trying to get myself a job there. (No luck so far.) After that, we went to a small winery called Casa Emma, where we had another super tour and then one of the best meals of our trip. They have a restaurant there that is only available to those who book tours, so not open to the public. We were treated first to the property’s olive oil, which I ended up buying a tin to bring home, and then as each course of the meal was brought out we were able to try their different wines. We had a sweeping view of their vineyards while we ate. That day, there were teams of workers out in the rows pruning the vines and getting them ready for the spring bud break. Casa Emma was a completely biodynamic vineyard and they had a flock of geese that patrolled the vines eating pests and leaving fertilizer in their wake. We were told they are let out early each morning and are free to roam and then when they are done feasting they come back to their enclosure on their own. No spraying, no pesticides, free food, talk about a win-win. Lunch was fantastic and afterwards we made our wine orders.

Marie loved the ceramic vessels at Casa Emma

After Casa Emma, we were off to San Gimignano, another magical Tuscan hill town. I had been here before in 2018, as had Mark and Marie. We parked in an otherwise empty parking lot and worked our way uphill to the city’s gate. Once inside, the town beckons you to explore its tiny streets and little shops. Marie bought wild boar filet mignon which was vacuum sealed for travel. I thought this was awesome; what a great thing to bring home. After exploring the town we grabbed a beer in a tiny cafe and were served by the local owners who spoke no English but treated us well, smiling at us as they sat drinking coffee a couple of tables over as we enjoyed our drinks. We had a dinner reservation that evening at Ristorante Perucà, a tiny restaurant with vaulted rooms of exposed bricks and artfully styled, modern Tuscan dishes, plus a long wine list. Located under a bridge that would not be easy to find if you didn’t go there ahead of time to be sure of where it was, which we had done. The food was superb and the wine, since it was our last night, was the best of the best. That was definitely a good day of eating, that’s for sure. After dinner we meandered back through the beautifully lit streets making photos and enjoying that after-dinner pace of life in Italy, which is to say, wonderfully s l o w.

Back in the parking lot we said our sad goodbyes. I headed back to Florence for the night and then headed back to the airport in the morning to catch a quick flight back to Nice. They drove to Rome the next morning and were able to get there with enough time to tour the Coliseum. Saying goodbye was especially heartbreaking for me as I love my friends very much and I enjoy every second of being together, even if they do smell like sulfur. I was fortunate enough to travel with them twice in the past year, once here in France and now in Italy, and knowing that it will probably be months or years before we get to do it again is very painful and certainly the worst part of moving to Europe for me. I miss them when we aren’t together. My Italian wines arrived quickly here in Nice and last night I opened one of the Lamole di Lamole Reservas. While I slowly savored every sip, I thought of them all very fondly remembering the laughter mostly, but also the incredible architecture, the friendly Italian people who treated us so well everywhere we went, the views, the food, and the great wine.

The great benefit of writing this blog is that these memories will patina over time and I can revisit them again and again, reliving each experience in my mind as I turn gray.

Siena and San Gimignano

Let’s read more

Siena and San Gimignano

Under Our Own Tuscan Sun

Let’s read more