Pisa, Siena & San Gimignano Day Trip with Lunch & Wine

Summary

From Florence to Pisa and Siena through vineyards, towers and old piazzas

You’ll start in Florence then wind through Siena’s medieval lanes with a local guide, taste a three-course lunch paired with Tuscan wines at a family-run winery near San Gimignano, and end your day marveling at Pisa’s Leaning Tower—all with stories, laughter, and plenty of time to wander on your own.

What’s the experience like?

The first thing I remember is the color of the light as we rolled out of Florence—soft gold on the bus windows, fields just waking up. Our guide, Claudia, pointed out olive groves and said something about how you can tell a real Tuscan by how they eat bread (no salt). I watched her hands as she spoke; she had that way Italians do, making stories with their fingers. By the time we reached Siena, my head was full of horse races and medieval rivalries I’d never heard of before.

Siena’s Piazza del Campo felt like stepping into a painting—except there were teenagers laughing on the steps and old men arguing over coffee. The city guide led us through narrow streets that smelled faintly of baking bread and stone dust. She told us about the Palio horse race and showed us where the neighborhoods hang their flags. I tried to imagine horses thundering around that tight curve. The cathedral was almost too much for my eyes—stripes everywhere, marble cold under my hand. I wandered off for a minute just to breathe it in alone.

The drive toward San Gimignano was all rolling hills and those cartoon-perfect cypress trees. Lunch at the winery came just when I needed it—three courses, each with its own wine (the red was peppery; I still think about it). There was laughter at our table when someone tried to pronounce “Vernaccia.” The owner’s daughter poured olive oil on our plates so we could dip bread—she winked when she caught me mopping up every last drop. Afterward, San Gimignano’s towers looked like chess pieces against the sky. We had an hour to wander; I bought gelato that melted faster than I could eat it.

Pisa came last, almost surreal after so much countryside. The Square of Miracles really does glow white in late afternoon—kids running on grass, everyone craning for that photo with the Leaning Tower (yes, we did it too). Claudia gave us tips on climbing if there wasn’t a line—I skipped it but sat on the grass watching clouds drift behind the tower instead. The ride back to Florence was quiet; someone snored softly behind me. Tuscany outside faded blue and green in the dusk.

Step-by-step itinerary

Day 1 — Explore Siena, San Gimignano, and Pisa

• Meet guide at Piazzale Montelungo
• Drive to Siena with guide commentary
• Walking tour of Siena city center
• Visit Piazza del Campo and learn history
• See Torre del Mangia clocktower outside
• Explore Siena Cathedral exterior independently
• Drive to winery near San Gimignano
• Enjoy three-course lunch with wine pairing
• Drive to San Gimignano
• Visit panoramic viewpoint and enter town
• Free time to explore San Gimignano
• Visit Piazza della Cisterna and Cathedral
• Drive to Pisa with guide commentary
• Explore Square of Miracles and monuments
• Optional climb of Leaning Tower of Pisa
• Visit Pisa Cathedral interior
• Return to Florence by coach bus

Top questions

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

The tour lasts a full day including travel time between destinations.

Is lunch included during this Tuscany day trip?

Yes, a three-course lunch with wine pairing is included at a countryside winery.

Do you get free time in San Gimignano?

Yes, you’ll have about one hour to explore San Gimignano independently.

Can you climb the Leaning Tower of Pisa during this tour?

If there is no queue during your free time in Pisa, you may be able to climb the tower.

Are entry fees for cathedrals included?

No, entry tickets for cathedral interiors are not included; you can purchase them separately if you wish.

Is transportation provided from Florence?

Yes, round-trip coach transport from Florence is included.

Is there a local guide in Siena?

A professional city guide leads your walking tour in Siena if you choose that option.

Does this tour include wine tasting?

Yes, wine tasting is paired with lunch at a family-owned winery near San Gimignano.

What’s included

Your day includes coach transport from Florence with WiFi onboard, guided walking tour of Siena (with headsets if selected), free time in both Pisa and San Gimignano, plus a three-course Tuscan lunch paired with local wines at a countryside estate before heading back in the evening.