After the downpour we had on day seven, I was a bit apprehensive at the start of day eight, Sunday, October 6th. But I needn’t have worried; the morning was crisp and cloudy, but the rain clouds were moving to the north. Our plan for the next leg of the journey called for us say farewell to Florence; we were going to rent a car, and drive almost due south, with our final destination for the day being Siena. We were slightly concerned about driving in Italy, but everyone that I’d spoken to back home had assured me that in Tuscany we would have no problems driving. (The Amalfi Coast is another situation entirely. All bets are off there…)

Getting the rental car proved to be a little bit of an ordeal. Finding the facility wasn’t the problem, it was fairly close to our hotel, within walking distance. The issue was that they had no cars available. Of course we’d reserved in advance, but once again we were reminded that we were not in America. The rental facility was not what you’d expect in the U.S. – there was no gigantic selection of cars at our fingertips, waiting for us in a large parking lot. No, this was a small storefront on a sidestreet in what is still a very medieval town. There was a small garage area where cars were being checked in and briefly cleaned; for the most part, someone would drive up to drop a car off, and it would be assigned to the next person waiting for one. When we got there, around 10:30 AM, there was already a large group of tourists waiting for a vehicle. It was well past noon by the time we got our car and were ready to go. The very nice man at the counter gave us a map, and explained to us as best he could how we should try to get to Siena.

We headed south across the Arno, and looked for signs for the “Autostradale Siena-Firenze”, which was the highway, or Autostrada, between Florence and Siena. Sounded simple enough. And actually, it was. We found the entrance to the highway without much trouble, and once we were on it, found it to be similar enough to a Texas highway that we were able to somewhat relax and enjoy the experience.

Tuscany is gorgeous.

The drive from Florence to Siena is only about an hour and half, and there are many beautiful hill towns in between the two cities. Our plan was to pick one, and enjoy the afternoon sightseeing, before continuing on to Siena. We decided to go to San Gimignano, which was probably number one on my list of Tuscan towns to explore. We took a wrong turn and were able to get a spectacular view. It was love at first sight. 

The town of San Gimignano has an extremely interesting history, dating back to the 3rd century B.C., when it was an Etruscan settlement. In the middle ages and during the Renaissance, San Gim prospered, due to its location on the medieval Via Francigena, the main route to Rome (and the Vatican) from countries to the north. The most interesting feature of the town are the towers that you can see in photos above. There are about a dozen of these still standing, but back in the San Gim’s heydey there were around 72 towers. These were built by rival families, in a massive game of one-upsmanship, and are what gives the town its nickname, the Medieval Manhattan. Sadly, the coming of the Black Death in 1348 put a stop to all such construction projects. At least half of the town’s residents perished, and the town was eventually forced to submit to the ruling powers of Florence.

But back to the here and now…San Gimignano is today a thriving tourist destination. It was probably our favorite of all of the hilltop towns that we visited. In spite of the fact that Rick Steves says that it’s “over-crowed and touristy”, we wouldn’t have missed it for the world, and actually we’ve said that if we ever go back to Tuscany we would love to stay in this town.

There are no cars allowed in San Gim, and so we parked at the bottom of the hill and joined the crowds of people walking up to the main gate. It was a beautiful fall day and to me it felt like a holiday; there was just that sense of “festival” in the air. 

We were pretty hungry by this time, and were looking for a spot to eat as soon as we walked into the town. Fortunately, one of the first places we came across was very highly rated on TripAdvisor, so we stopped in. The restaurant was called Bel Soggiorno (it’s also a hotel). The setting couldn’t have been more perfect – a gigantic wall of windows offered a magnificent view down into the valley. (And yes, the food was delicious too.) 

After lunch, we set off to explore the town. We truly loved it there and wished that we could have spent more time there; we easily could have spent a day or more there, and not just an afternoon. Touristy? Well, maybe, but it was still arguably one of the most picturesque and beautiful little towns I’ve ever had the great fortune to visit. 

View of the valley: 

More San Gim street scenes: 

This is where we began our love affair with the doors of Tuscany.

We eventually had to leave beautiful San Gimignano, if we wanted to make it to Siena by nightfall. Another adventure was behind us, but there were more on the road ahead.