Tuscany: Pisa, Siena & San Gimignano Day Trip with Chianti Wine

4.64

(646 reviews)

What’s the experience like?

I’ll admit, I was mostly curious about the Leaning Tower of Pisa—everyone talks about it, but seeing it tilt in real life is stranger than photos suggest. We started early from Florence, still a bit sleepy, and suddenly there it was: bright marble against a blue sky, tourists everywhere trying their “holding up the tower” pose (I tried too, badly). Our guide Marta pointed out some details on the Baptistery—she said if you stand just right inside, you can hear your own echo bounce back at you. I didn’t try it but now wish I had. The grass around Piazza dei Miracoli smelled fresh after last night’s rain; people were lying down just soaking up the morning. It felt calm in a way I didn’t expect from such a famous place.

The drive into the Chianti hills was all winding roads and sudden flashes of vineyards—honestly, it looked like every postcard I’d ever seen. Lunch was at this rustic winery near San Gimignano. They served pecorino and cold cuts with three different wines (the third one was my favorite—fruity but not too sweet). There was laughter at our table when someone tried to swirl their glass like an expert and nearly spilled it. The owner explained how the soil changes the flavor—I pretended to understand but mostly just enjoyed the bread dipped in olive oil. The air smelled like rosemary and something earthy I couldn’t quite name.

San Gimignano surprised me most. Those medieval towers really do make it look like a stone forest from far away. We wandered cobbled streets that twisted between old brick houses; I lost track of time poking into little shops selling ceramics and saffron candies (bought some for later). Marta told us about rival families who built taller towers just to show off—some things never change, right? It got busy in the main square but somehow didn’t feel crowded, maybe because everyone seemed as distracted by gelato as I was.

Siena came late in the afternoon when everything glowed gold. Our local guide led us through quiet Contrade alleys—she waved at neighbors who nodded back without stopping—and then out into Piazza del Campo where kids were chasing pigeons under that shell-shaped sweep of bricks. The Duomo’s striped marble looked almost unreal in that light. Afterward we had free time; I sat outside with coffee and panforte (dense, spicy cake) just watching people pass by. There’s something about Siena that lingers—a kind of hush even with all the movement. I still think about that moment sometimes when things get noisy back home.