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

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Duration10h

GroupPrivate

LanguagesEN

PickupAt your hotel

Private Tuscany tour from Florence with Siena wine towns Pisa

You’ll start with hotel pickup in Florence and spend your day exploring Siena’s medieval charm, tasting Chianti wines at a local spot, wandering San Gimignano’s ancient towers, and snapping photos at Pisa’s Leaning Tower—all at your own pace with a friendly local driver guiding you along winding Tuscan roads.

10h

Step-by-step itinerary

Tuscany day trip from Florence

Pick up at Florence accommodation
Drive to Siena, admire countryside
Visit Siena: Piazza del Campo and cathedral
Drive to San Gimignano, optional lunch
Explore San Gimignano towers and shops
Visit Pisa: Leaning Tower and cathedral
Drive back to Florence accommodation

The Experience

“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.

What’s included

Your day includes hotel pickup in Florence by an English-speaking driver with a comfortable Mercedes vehicle (WiFi and bottled water onboard), all fees and taxes covered, plus flexibility to adjust your route as you go—so you can linger over lunch or spend extra time wherever something catches your eye before returning home relaxed in the evening.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by Prestige Rent