Exploring Italy, Pt. 5: San Gimignano, Siena, Cortona, Bologna, and More! (2023)

Whew, at this point, it feels like a recap is in order. So far, on this journey we've visited these places in southern Italy:

Naples and Capri, Lecce/Otranto/Torre San Giovanni/Santa Maria di Leuca, Rome and Vatican City, Montepulciano

This part of the trip will be taking us to various parts of (mostly) Tuscany:

San Gimignano, Volterra, Pisa, Lucca, Cortona, Siena, Parma, Bologna, Florence, Verona

Now, for the travel journal...

San Gimignano:

From the hilltop town of Montepulciano, we are heading north, further into the heart of Tuscany. Approaching our destination - San Gimignano - feels like stepping into a painting. It truly doesn’t seem real. Fourteen medieval towers dominate the skyline, where 72 of these structures once stood. Over the centuries, some of them fell into disrepair and collapsed, some were removed, and some were damaged during World War II.

In 1990, the town became a World Heritage Site, and the ongoing effort to preserve this unique place is evident by the scaffolding surrounding some of the buildings. San Gimignano is so unique and beautiful that visiting here again renews my sense of wonder and awe.

Like many places in Italy, the town is within a ZTL zone, so most visitors need to park in one of the public lots and walk in via one of the historic city gates. (If you’re planning a trip to this country, be sure to check out this popular post: “Italy: Avoiding Traffic Fines While Renting a Car and Safe Driving Tips”.)

The narrow streets here wind and slope upward toward the central plaza. They’re slippery when wet, and all this walking requires a comfortable pair of shoes with good grip anyhow. A lot of spots are steep like this:

It’s getting late, so we have a nice pasta dinner and cap off the night in town with some gelato… “Gelato World Champion” the shop in the main square proudly proclaims on its sign. This dessert is good but certainly nothing above-and-beyond some we’ve had elsewhere in Italy.

With sticky fingers from the melted ice cream, it’s time to head back to the farmhouse B&B, a few hills away, and get settled in for the night.

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The summer heat is quickly warming up the new day, and we hit the road to explore more of Tuscany. Our rough itinerary today is: Volterra, Pisa, and Lucca. Tomorrow: Cortona and Siena.

Volterra:

The stop in Volterra is a quick one. In the “Twilight” series, this is the center of the vampire world, where its clan of royal rulers is based. It feels like a random choice, and I've learned it kind of was, with the initial criteria being that it's 1) a Tuscany location, and 2) has a clock tower in the town square. We don’t see any vampires, good thing, or notice any traces of Hollywood here, which is also a good thing.

If you're on the hunt for anything made from olive wood, this is a good place to shop for it. Ultimately, this is a small town that probably sees a lot of traffic more because of the movies than any specific landmarks. There are some neat ruins of a Roman theater nearby, which we didn't have a chance to see, and otherwise there doesn't seem to be anything enticingly unique here that's worthy of a visit. Still, Volterra is pretty and appears to be well-maintained, but there's little need to prioritize a visit here.

Pisa:

We drive about 30 minutes northwest and arrive in Pisa. The center of town, featuring the iconic Leaning Tower, is packed. Out of the way, people! We need to get the photos you’d expect, of us holding the tower up. They’re goofy and for our own fun, so I’m not gonna post those. Check out this lean, though! A lot of science, money, and time have kept this landmark from toppling over...

The wind is picking up, and dark clouds are rolling in, so we head back to the car. Hopefully the rain holds off long enough for us to take a walk around the city of Lucca, which takes almost another 30 minutes by car from Pisa.

Lucca:

The rain starts just as we park, so we huddle under an umbrella and walk toward the city walls. Fortified cities are so common in Tuscany, but this one is unique. Stone staircases within the walls lead you up to the top of the 16th and 17th century ramparts. These are so wide, it’s easy to forget this is the top of a fort.

During a break from the rain, we sit down on some wet chairs at an outdoor cafe and each order a spritz. Sometimes that bright orange aperitif is just so easy to gulp down.

From here, we stroll through town, then, once the rain picks back up, we head back toward San Gimignano.

A couple hours later, back at the B&B, the rain has stopped, yet again, but the landscape is unlike anything I've ever seen before. In our room, I have to stand on the bed and shimmy halfway through a small window to take in this gorgeous sight:

Cortona:

Cortona is on our radar from the film "Under the Tuscan Sun". If you've never seen it, that one does a really great job of portraying the natural charm this region exudes. Like Diane Lane's character, there's a part of me that would love to reinvent myself somewhere with a slower pace of life. The time I spend scrolling through social media or the news feed on my phone could be better utilized doing something that impacts my actual reality.

As for visiting the "Under the Tuscan Sun" version of Cortona, it can be confusing... Some info we saw online took us to one place. "This doesn't look right", we said amongst ourselves, while viewing this house:

It turns out, this is the book version, where author Frances Mayes actually did restore the house (Villa Bramasole) and write a memoir about her experience here. Then there's the movie version, depicting the same story but in a different part of Cortona (Villa Laura). We didn't see the latter, because Google Maps shows the house as being beyond a gated street. It's actually one street further south, literally right next to a public road.

As we descend from Cortana, I peek back a few times, in case I can catch a glimpse of the house shown in the movie. I don't and soon shift my focus on our next destination: Siena.

Siena:

Somehow, Siena both warms and breaks my heart. During this trip, I've had that conflicted feeling each time we've driven past signs for that city while exploring this area. Jumping ahead (because Siena is in a ZTL zone, and who wants to hear about that again?), on this Sunday night, Piazzo del Campo (the main square), is lively. Next to a D.J. is a booth selling plates of food with an Aperol Spritz for just 5 Euros. Sign us up!

Sitting in the main square, eating, drinking, people-watching, and seeing the puffy clouds slowly transit behind the medieval clock tower brings back memories of the last time we were here. There's something about this place I can't quite put my finger on... and my emotions well up, almost to a watery breaking point. This is... odd. Apparently I left a piece of my heart in this city 11 years ago. I can't explain it. This probably wouldn't be the same experience for you, but this place calls out like a second home for me.

As the sunlight starts to fade, we head back to the car. It'll be about an hour drive back to San Gimignano, where some of the old, winding, unlit gravel roads are narrow and feel dangerous.

Soon enough, only our headlights show us the way, as the navigation on my phone keeps cutting out... The signal returns just before the road splits, and it has us going to the left.

Uhh, the road is now gravel and feels like it's cutting through an orchard, with a farmhouse straight ahead. The navigation app shows this is still a road, so we drive drive to the back of the house. This definitely isn't a road!!! We decide to backtrack and, as we make a full circle around the home, I can see someone peeking out at us from an upstairs window. It understates the panic in this moment, but "unfortunate" is the only word that initially comes to mind to describe this experience.

Back on the paved road, whew, it's only another 10 minutes before we are back "home".

Bologna:

Relatively speaking, Bologna is one of the lesser-known Italian cities but still has its own identity and charm. The remaining towers ("Due Torri") are the main landmark here, similar to the fourteen still standing in San Gimignano. These two are literally almost a thousand years old, dating back to the 1100s, and they were likely built by two competing, powerful families.

The shorter tower (called "Garisenda") was shortened even more in the 1300s, when the shifting ground below led to fears the tilting structure could collapse. That fear was officially renewed in 2023, and like in Pisa, a lot of science, time, and money are being put into keeping one of the unique and historic symbols from being lost forever.

The tower next door ("Asinelli") is open to the public, so we figured "Why not work up a sweat and feel our legs burn as we walk to the top?" Buying timed tickets online with my phone is a breeze, and 10 minutes later, we are waiting in line, ready to go up.

Just as it feels like my legs are about to explode, we reach the top. The strong breeze feels amazing, and it doesn't take long for my sweaty shirt to dry. The cityscape is beautiful but, like in Paris, the best views include the landmark instead of being from it.

Florence:

Our brief stop in Florence is a little challenging. When we stayed here before, over a decade ago, we checked out the Uffizi Gallery, saw Michelangelo's "David" statue, crossed the iconic bridges, and more. This time, we are only here long enough to watch the setting sun and have dinner.

The most popular, scenic sunset view is from Piazzale Michelangelo, which offers a great perspective of the city. The heavy traffic seems to indicate we're getting here too late, and we end up taking a wrong turn. Luckily, that ends up working out great: a parking spot opens up right in front of the viewpoint.

This park offers a really great view, but the experience here is a little too chaotic for our liking. Plus, after sunset, we know it will be a mad dash out of here and, like us, many of these people will soon be on the hunt for dinner. With that in mind, we take some photos, then head back into the city.

Parking in central Florence seems almost too easy. We lock up the car and double check the street signs before walking away. The message isn't totally clear, but all the vehicles along this street seem to be displaying parking permits. Dang it! We get back in the car and head closer to town. Right next to the central market, one parking spot opens up. Here also, the restrictions aren't entirely clear, but it seems this section is reserved for delivery drivers. A (very expensive) parking garage is nearby, but it feels like we have no choice.

The Mercato Centrale (Central Market) is nearby, so we decide to check out the dinner options there. "This is great; there's something for everyone", I think to myself, but someone in this party of two doesn't see anything that seems appetizing.

We hit the streets again and, for once, get roped into one of those restaurants where someone is standing outside with a menu, asking everyone walking by if they are hungry and looking for a good meal. Yeahhhh, we are, and as the streets are quickly becoming more crowded, it feels like we are running out of options. Dinner isn't particularly enjoyable, but you win some, you lose some.

Verona:

We finally check out from our home base in San Gimignano and head north, to Verona. Tonight we will be seeing the opera Aida, performed in Italian in an arena that looks a lot like the Colosseum in Rome, but smaller and more intact. It's older, too, having been completed in AD 30 (vs. ~AD 70-80 for its Roman counterpart).

Our drive north is about 3 hours, putting us closer to Venice and Switzerland than where we've been exploring in Tuscany. Aside from the arena, the biggest draw in Verona may very well be "Juliet's balcony" (Casa di Giulietta), with this being the most important setting in Shakespeare's "Romeo and Juliet" play, dating back to the 1500s... Yet, this particular addition was built in the 1930s. It was never really "Juliet's balcony". Regardless, if anyone finds visiting it inspiring or fun, I support that. I'm definitely not paying any amount to take a selfie on the balcony, though. Viewing it from the small square below is free and, during our visit, it's completely packed with visitors!

In the evening, it feels like everyone in town is walking toward the arena. The vibe inside the place feels incredible and exciting. It's like the walls give off a mysterious energy, from all the place has seen after being around for 2,000 years.

Authentically, the seats are stone. We knew about this ahead of time and brought the seat cushions we use on long flights. Even with those, it's uncomfortable sitting for a while on stone with no back support. The performance of "Aida" is really a spectacle. It's hard to describe the scale of this show... At one point, I count at least 150 performers onstage, and the official number is probably much higher! The outfits and props are amazing, the stage has trapdoors, the show makes really neat use of lasers, and the arena's acoustics are really remarkable. The show lasts from 9 PM to just beyond midnight and includes an intermission. By the end, it feels as late as it is. We walk back "home" and, in between yawns, talk about what our favorite parts of the show were. What an incredible experience. We did plan this part of our trip completely around wanting to see a performance in the Verona Arena, and I'm glad that worked out so well.

Parma:

It's a new day and, seriously, our primary reason for visiting this city is to try Parma ham (prisciutto di Parma). This specialty has a protected status in the European Union, with strict production guidelines... The only allowable ingredients are sea salt, air, and time. No additives, no preservatives.

Without much warning, it seems we drove into a ZTL zone. Seriously, if you have any plans to drive in Italy, read this free guide:

"Italy: Avoiding Traffic Fines While Renting a Car and Safe Driving Tips"

We find metered parking on the street and take a short walk into town. It's a little early for lunch, so we order a ham plate to share, which comes with (of course) a chunk of high-quality, crumbly, Parmesan (Parmigiano Reggiano) cheese. The combination is good. It's not exactly the best thing I've ever eaten... Although, as an American, where artificially processed, artificially tasty products are so prevalent for the sake of capitalism (instead of health), it's important to at least try to find some appreciation for traditional foods like this.

Well, that wraps up this portion of the trip. Next, we'll cover Milan, Cinque Terre, and Lake Como, then start to wrap up this trip in Switzerland.

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"Exploring Italy, Pt. 5: San Gimignano, Siena, Cortona, Bologna, and More! (2023)"

Written by: Justin Kilmer

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