We left Florence today to explore other parts of Tuscany on a motor coach with a bunch of fellow tourists. When building the itinerary, I really wanted to spend more time in Siena—the city I lived in during summer school back in 2010. But there’s so much of Italy we wanted to see and do, so we compromised and made Siena part of a day trip instead of an overnight stay.

Our group meeting time was 7:45 a.m. by the train station. I always build in a little “buffer time” in case we run late or get lost, and when we don’t, that time gets reallocated to coffee and cornettos. This morning, however, Matt forgot his wedding ring in the apartment, and I insisted we go back for it because, “I don’t know these people.” In other words, our buffer time was used for asset preservation. It works out well for us—don’t worry.

Our bus left on time, and we made our way toward the beautiful medieval town of Siena. Our tour director, Christian, gave us a few tidbits along the way and let us know we’d be handed off to a local guide once we arrived. The weather had originally called for cold and rain, but within minutes of getting there, the sun came out—and stayed out for most of the day.

Our local guide, Alessandra from the Porcupine Contrada, was an absolute delight. She walked us through Siena’s 17 contrade, explained the famous horse race, and even pointed out Europe’s oldest still-functioning bank. We also learned that Siena was largely spared during the war because of its medieval beauty—although the train station just outside the city wasn’t so lucky.

We made our way to Siena’s stunning duomo and were then set free to explore on our own.

Naturally, I took Matt to see my old residence in the northwest corner of the city center. For some reason, Siena’s hills feel much less offensive than Rome’s. Don’t get me wrong—they’re steep—but either my muscle memory is still there, or the past few days have been solid training.

I was slightly worried I’d overwhelm Matt with nostalgia and old stories, but he seemed to genuinely enjoy seeing me soak it all in. Happy wife, happy Matt, I suppose.

From there, we stopped at Torrefazione Fiorella for cappuccinos and pastries. I ordered a Nutella croissant that was absolutely bursting at the seams—sharing Nutella with everything it touched. Matt went for a much more modest lemon sugar croissant. We took our treats to Piazza del Campo and enjoyed them while taking in the view. Just as beautiful as I remember.

What I don’t remember is the number of tour groups swarming the city—but that might just be selective memory. I’ll have to check with my friends. I wish we had more time, but we had three more stops ahead.

Next up was lunch and a wine tasting at a Tuscan winery. As soon as we arrived, we were seated, served food and wine, and given a quick rundown of what we were drinking and when. We sat with two other couples—one from Australia and one from Texas. Somehow, we always end up running into Australians when we travel.

Everyone (except me) tasted four different wines, including a dessert wine that completely overwhelmed the table. Naturally, Matt and I bought more of it and had it shipped home. After lunch, we wandered outside and took tons of photos of the rolling hills and vineyards. The bus ride leaving was… lively, thanks to everyone’s four glasses of wine.

Next stop: San Gimignano—an adorable medieval town that once had 72 towers (now only 14 remain). We had three missions here:

1. Visit Piazza della Cisterna
2. Get world-famous gelato from Gelateria Dondoli (the line stretched halfway through the piazza, but they run more efficiently than Chick-fil-A, so it moved fast)
3. Find a panoramic viewpoint

Mission accomplished on all three.

Our final stop was Pisa. Most Italians will tell you that you don’t need a full day there—and they’re right. We popped in, took our required tourist photos, grabbed a coffee, and of course picked up a leaning tower magnet. One shop owner “guessed” we were from the West Coast. I was impressed—“Yea! How did you know?!” He laughed, pointed at Matt’s bag, and said, “I saw your document—California!” I laughed way harder than necessary, which made him laugh even harder in excitement, like he finally got someone to laugh at his “joke.”

The bus ride back was about an hour and twenty minutes, and—just as expected—we arrived nearly an hour late to Florence. My pre-trip Reddit research had already warned me this was normal. Italian schedules are… flexible.

Anticipating that, I made our dinner reservation weeks ago for 9:00 p.m. at a well-known steakhouse, Trattoria Dall’Oste, and we arrived right on time! 

So far, today has been our highest step count—and somehow, my legs and feet aren’t even mad about it. Thank God.