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

Summary

From Pisa’s Leaning Tower to Chianti hills and Siena’s medieval heart

You’ll wander Pisa’s famous square, taste wine among Chianti hills with lunch included, explore San Gimignano’s medieval lanes, and end your day tracing Siena’s Contrade with a local guide before returning to Florence—all those small sensory moments will stay with you longer than any photo.

Step-by-step itinerary

Day 1 — Pisa, Wine Tasting, San Gimignano, Siena

• Depart from Florence city centre
• Tour Pisa cathedral and baptistery
• Visit Monumental Cemetery of Pisa
• Admire Piazza dei Miracoli
• Optional climb Leaning Tower of Pisa
• Drive through Chianti countryside
• Wine tasting and light lunch at Chianti winery
• Explore San Gimignano cobbled streets
• View Piazza del Duomo and Piazza della Cisterna
• Panoramic Chianti countryside view
• Guided tour of Siena squares and Contrade
• Free time for coffee and shopping in Siena
• Return to Florence city centre

Top questions

How long is the day trip from Florence to Pisa, San Gimignano & Siena?

The tour lasts a full day, departing early morning from Florence city center and returning in the evening.

Is lunch included on this Tuscany day trip?

Yes, a light lunch is included at a winery in the Chianti area along with wine tasting.

Can children climb the Leaning Tower of Pisa?

No, entry to the Leaning Tower is not allowed for children under 8 years old.

Does this tour include guided visits or free time?

You’ll have both—a guided tour in Siena plus free time in Pisa and San Gimignano to explore on your own.

Are vegetarian or special dietary menus available for lunch?

Yes, vegetarian or special menus can be arranged if requested after booking by email.

Where does the tour start in Florence?

The meeting point is at Sightseeing Experience Visitor Center inside Santa Maria Novella Train Station.

Is transportation provided between all destinations?

Yes, transfers are by air-conditioned bus with Wi-Fi onboard throughout the day trip.

Do you need to book Leaning Tower tickets separately?

You can select an option including Leaning Tower entry when booking; otherwise tickets are not included by default.

What’s included

Your day includes comfortable pickup from Florence city center by air-conditioned bus with Wi-Fi; guided walking tour in Siena; free time in Pisa and San Gimignano; entry fees if selected (including optional Leaning Tower access); a traditional light lunch at a Chianti winery paired with three local wines before heading back to Florence in the evening.

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.