Tuscany Day Trip: Pisa, Siena, San Gimignano & Chianti Lunch

Summary

Medieval towers and rolling vineyards on a Tuscan journey

You’ll taste real Tuscan wine over lunch in San Gimignano, wander medieval streets in Siena with a local guide, and see Pisa’s Leaning Tower up close — all in one long but lively day trip from Florence. Expect laughter over mispronounced wines and quiet moments inside ancient cathedrals that might stay with you longer than you think.

What’s the experience like?

The first thing I noticed in Pisa was the grass — it’s almost too green, like someone painted it on. Our guide, Marta, led us straight across the Field of Miracles, where the Leaning Tower really does lean more than you expect (my photos are all a bit crooked). There was this faint smell of old stone and something sweet from a nearby bakery. Marta explained how the cathedral took centuries to finish — I kept glancing up at the marble carvings while she talked. She had this way of slipping in little stories about Pisan pride that made me smile.

After Pisa, we drove through hills that looked like they belonged in a painting. The bus windows fogged up for a minute when we passed through some early mist — I wiped mine clear just in time to see rows of cypress trees and those tiny villages clinging to hilltops. Lunch in San Gimignano was loud and warm: big wooden tables, glasses clinking, bread with olive oil that tasted peppery. The wine tasting kind of snuck up on me (four types — I lost track after the second). Someone at our table tried to pronounce “Vernaccia” and got everyone laughing. Walking around afterwards, the towers made weird shadows over the square. It felt like time had slowed down there.

Siena came last. We followed our local guide through narrow streets where laundry hung between windows and old men argued softly outside cafés. The Piazza del Campo is bigger than it looks in photos — I just stood there for a second trying to take it all in. Inside the cathedral, everything echoed: footsteps on marble, whispers bouncing off mosaics. I kept thinking about how many people have walked here before me. My audio guide slipped off my ear once and startled me with feedback — nobody seemed to mind.

I didn’t expect to feel so full by the end — not just from lunch but from everything packed into one day trip from Florence to these places I’d only seen in books before. Even now, sometimes when I smell fresh bread or see sunlight on old stone, I think back to that day.

Step-by-step itinerary

Day 1 — Explore Pisa, San Gimignano, and Siena

• Visit Pisa Field of Miracles
• See Pisa Cathedral (Duomo)
• View Leaning Tower of Pisa
• Visit Pisa Baptistery
• Drive through Tuscan countryside
• Enjoy Tuscan lunch with wine in San Gimignano
• Explore San Gimignano medieval village
• Visit Piazza della Cisterna in San Gimignano
• Drive through Chianti countryside to Siena
• Walking tour of Siena historic center
• See oldest bank in Siena
• Visit Siena Cathedral (Duomo) if option selected

Top questions

How long is the Tuscany day trip from Florence?

The tour lasts approximately one full day including travel between Pisa, San Gimignano, Chianti countryside, and Siena.

Is lunch included during the Tuscany tour?

Yes, a traditional Tuscan lunch with wine tasting is included if you select that option when booking.

Are entrance fees for cathedrals included?

Entrance and guided visit to Siena Cathedral are included if you choose that option during booking.

Is transportation provided between cities?

Yes, comfortable air-conditioned coach transport is provided throughout the day trip.

Do I need to bring my passport or ID?

Yes, bringing your original ID is required for this tour.

Are audio guides available during tours?

Earphones are provided for better enjoyment during the guided tour in Siena.

Can infants join this Tuscany day trip?

Infants can join; strollers are allowed and specialized infant seats are available upon request.

Is this tour suitable for wheelchair users?

No, unfortunately transportation and some sites are not suitable for wheelchair users or those with motor disabilities.

What’s included

Your day includes pickup at the meeting point in Florence, comfortable coach transport between Pisa, San Gimignano (with traditional Tuscan lunch and four-wine tasting if selected), Chianti countryside views en route to Siena, entrance fees for Siena Cathedral (if chosen), use of earphones during guided tours so you don’t miss anything even in busy squares, plus help from dedicated staff throughout your journey.