Florence to Tuscany: Siena, San Gimignano, Pisa Day Trip & Lunch

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Duration8h–12h

GroupUp to 8

LanguagesEN

Mobile ticketAccepted

Tuscany’s timeless towns, rolling hills and slow lunches from Florence

You’ll join a small group for an easygoing day trip from Florence through Tuscany’s most iconic towns: stroll medieval Siena with a local guide, sample sweet treats and regional wines, wander San Gimignano’s ancient streets at your own pace, sit down for a relaxed Tuscan lunch in Chianti countryside, and end with free time beneath Pisa’s famous Leaning Tower—returning home with more than just pictures.

8h–12h

Step-by-step itinerary

Tuscan towns and countryside tour

Meet tour leader at Piazza Mentana
Depart Florence by luxury minivan
Enjoy panoramic Chianti countryside views
Guided walking tour of Siena
Local tasting of traditional Tuscan flavors
Travel to San Gimignano via Via Cassia
Free time to explore San Gimignano
Tuscan lunch in Chianti area
Free time at Pisa’s Piazza dei Miracoli
Return to Florence by evening

The Experience

“You’ll never remember all these Contrade,” our Siena guide teased, waving her hands as if she could scoop up the whole city’s history. I was still chewing a ricciarelli cookie — almondy and soft, not too sweet — so I just grinned and nodded. The morning air in Siena had that stone-and-espresso smell you only get in old Italian cities. We wandered through narrow lanes with faded flags above us, sunlight bouncing off the Duomo’s white marble. I kept falling behind to stare at shop windows or listen to snippets of Italian conversations. Our group was tiny (eight of us), which made it easier to ask silly questions or just hang back without feeling rushed.

After Siena, our driver Luca took us winding through the Chianti countryside. It’s one thing seeing those cypress trees in photos — but actually watching them flick past your window is something else entirely. We stopped for a “surprise tasting” (I won’t spoil it), and then rolled into San Gimignano. The towers really do look like something out of a storybook — I tried climbing one for the view but got distracted by a tiny wine shop instead. Vernaccia white wine tastes like summer in a glass; I’m not sure how else to describe it. There was time to wander on my own, which felt rare and good.

Lunch was at this farmhouse with long wooden tables and mismatched chairs. Plates of fresh pasta kept appearing, along with Chianti wine that tasted earthy and bright at once. Someone’s phone played Italian pop quietly in the background while we all swapped stories about where we were from. The food wasn’t fancy but it felt right — simple flavors, olive oil you could almost drink straight.

Pisa came last — honestly, by then my legs were tired and my brain full of new names and places. Still, seeing the Leaning Tower in person made me laugh (it really does lean more than you expect). Kids were posing for those classic “holding up the tower” photos; I tried too but failed miserably. On the drive back to Florence, golden light spilled over the vineyards and everyone went quiet for a while. I still think about that silence sometimes — just tired-happy after a day that didn’t feel rushed or forced, just…full.

What’s included

Your day includes round-trip transport from Florence by luxury minivan (with Wi-Fi), guided walking tour of Siena with a licensed local guide, surprise tasting stop (think sweet treats or seasonal specialties), free time in San Gimignano plus a winery visit with tasting, traditional three-course Tuscan lunch paired with local wines in Chianti countryside, and relaxed exploration of Pisa’s Miracle Square before heading back home.

Good to know

Easy physical levelInfant seats availablePublic transport nearby

Operated by Towns of Italy