Tuscany Day Trip: Siena, San Gimignano, Chianti & Pisa Private Tour

4.97

(123 reviews)

What’s the experience like?

“Is that really the Leaning Tower?” my friend whispered as we pulled up to Pisa’s Miracle Square—honestly, it looked even more tilted in person. But our day started way before that, when our driver Marco met us outside our Florence apartment (he was early—classic). He had this easy way of explaining the route while we passed those soft green hills and rows of olive trees. I kept thinking I’d seen these views on postcards, but they’re quieter in real life. The car even smelled faintly like rosemary when we rolled down the window near Greve.

Siena was next. The old stone streets felt cool underfoot and we could hear someone practicing violin behind a shuttered window near Piazza del Campo. Marco pointed out where the Palio horse race happens—apparently the whole city stops for it twice a year. We wandered into a bakery for ricciarelli (I’m still not sure how to pronounce it—Marco tried to teach me), and I swear I can still taste that almond sweetness. I liked just watching locals chat by the cathedral steps, hands flying everywhere.

Lunch happened somewhere between Siena and San Gimignano—a tiny trattoria Marco suggested. It wasn’t fancy but the Chianti was peppery and deep, and the bread had this rough crust that left flour on my fingers. In San Gimignano, those towers really do crowd the sky; you can almost imagine medieval families competing for who could build higher. My shoes got dusty walking those lanes lined with ceramics and linen shops—I bought nothing but wanted everything.

Pisa was last. There were crowds but also this hush around the Baptistery—maybe everyone just runs out of words after seeing that tower lean so stubbornly. We took silly photos (obligatory) and then just sat on the grass for a bit, tired in a good way. The drive back to Florence felt slower; maybe because we didn’t want it to end yet.