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

Summary

San Gimignano towers, Siena’s piazza, Chianti lunch and wine

You’ll wander medieval lanes in San Gimignano and Monteriggioni, taste three Chianti wines over a Tuscan farm lunch, and lose track of time among Siena’s Gothic streets. Expect laughter with your local guide, free time for gelato or photos, and those little moments—like dipping cantucci into sweet wine—that stick with you long after Florence fades behind.

What’s the experience like?

I didn’t expect to feel so small standing under those towers in San Gimignano. They rise up out of the stone like something out of a storybook—except you can smell the bakery on the corner and hear Italian teenagers shouting across the piazza. Our guide, Marta, handed us a map but mostly just grinned and told us to “get lost” for an hour. I tried my first saffron gelato here (weirdly good), then found myself staring over the Val d’Elsa valley, olive trees glinting in the sun. I still think about that view sometimes.

We rolled into Monteriggioni next—tiny place, honestly. The kind of spot you’d miss if you blinked from the bus window, but inside those old stone walls it felt like time just…slowed down. There was a guy fixing his bike by the gate and two old women arguing over tomatoes at a little stall. Didn’t stay long, but I snapped a photo from the ramparts that looks fake now—blue sky, green hills, all that.

The best part? Lunch at this family-run winery somewhere along the Chiantigiana road. The air smelled like rosemary and earth when we stepped out. They poured three different Chianti wines (I liked the second one best—can’t remember why), and brought out plates of pasta and roast pork that tasted like someone’s grandma had made them. We dipped cantucci into vin santo at the end—Marta told us it’s rude not to dunk them, so we did. She laughed when my cookie fell in.

Siena was busy in that warm way cities get before dinner—locals chatting by shop doors, students sprawled on the shell-shaped Piazza del Campo. The Duomo looked almost unreal with its black-and-white stripes; we ducked inside for a quick look at the mosaics before wandering off down some narrow lane smelling faintly of leather and espresso. I bought a tiny bottle of olive oil from an old man who insisted it was “the real thing.” Maybe it is—I haven’t opened it yet.

Step-by-step itinerary

Day 1 — Tuscany tour: San Gimignano to Siena

• Explore San Gimignano historic center
• Visit Monteriggioni fortress village
• Drive scenic Chiantigiana road
• Enjoy wine tasting and lunch at winery
• Free time to explore Siena city
• See Siena Cathedral exterior and interior
• Visit Piazza del Campo and relax

Top questions

How long is the Tuscany day trip from Florence?

The tour lasts about 11 hours round-trip from Florence.

Is lunch included on this San Gimignano & Siena tour?

Yes, a three-course Tuscan lunch with wine tasting at a Chianti winery is included.

Does this tour include Monteriggioni?

Yes, except from November to March when Monteriggioni is skipped and return to Florence is earlier.

Are entrance fees to Siena Cathedral covered?

The tour includes an exterior visit and brief interior look at Siena Cathedral; full entry may not be included.

Is transport provided between Florence and Tuscany towns?

Yes, round-trip transport by air-conditioned coach is included in your booking.

How much free time do we get in each town?

You’ll have free time to explore both San Gimignano and Siena independently during the day trip.

Is this tour suitable for children or infants?

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

Do I need to bring anything special for this Tuscany day trip?

You must bring your original ID for check-in; comfortable walking shoes are recommended.

What’s included

Your day includes smooth check-in support at Florence’s meeting point, round-trip coach transport through Tuscany’s hills, an English-speaking guide escorting you throughout (sometimes replaced by a driver-guide for small groups), guided cellar visit plus three-course Tuscan lunch with three Chianti wines at a cozy winery (with extra virgin olive oil tasting), time to explore San Gimignano and Siena on your own—including quick visits to Monteriggioni (seasonal), Siena Cathedral exterior/interior highlights—and classic cantucci with vin santo before heading back in the evening.