Florence to Siena, San Gimignano & Chianti: Private Day Trip

Summary

Siena’s piazza heat, chianti vineyards and medieval towers in one tuscan day

You’ll feel Siena’s energy in its main square, taste real Chianti wines at a local vineyard (with lunch if you want), and walk through San Gimignano’s medieval lanes—all with a private guide handling every detail. There’s time for wandering, tasting, maybe laughing at your own Italian pronunciation—and space to let Tuscany sink in.

What’s the experience like?

Ever wondered what it feels like to actually stand in Siena’s Piazza del Campo, not just see it in photos? I didn’t expect the square to feel so alive—there was this low hum of voices and the smell of coffee drifting from somewhere nearby. Our driver, Paolo, pointed out the Palio flags fluttering above us and told us how wild the city gets during the race. He laughed when I tried to pronounce “contrada”—I’m still not sure I got it right. We wandered through narrow streets that felt older than time itself, ducking into a bakery for ricciarelli that left powdered sugar on my shirt (worth it). The Siena Cathedral looked almost unreal up close—black and white stripes against the sky, cool marble under my hands.

The drive through Chianti was quieter than I thought it’d be. Vineyards rolled by in green waves, with cypress trees pointing straight up like exclamation marks. At the winery stop—optional but honestly, don’t skip it—the air smelled faintly of earth and rosemary. Lunch was all local: fresh pasta with wild boar sauce and a glass of Chianti Classico that tasted somehow both sharp and soft. The winemaker explained each pour in a mix of English and rapid Italian; I caught about half but felt all of it. If you’re into wine at all, this is your spot.

San Gimignano came later, its towers poking out of the hilltop like something from a storybook—except there were teenagers taking selfies everywhere, which sort of broke the spell but also made me laugh. The gelato shop everyone talks about really is that good; pistachio for me, though my friend swears by saffron. By then my feet hurt a bit and the sun had started sliding down behind those old stones. Heading back to Florence in the minivan (which had cold water ready—bless), I kept thinking about how every part of Tuscany seems built for slow days like this.

Step-by-step itinerary

Day 1 — Explore Siena, Monteriggioni and San Gimignano

• Arrive in Siena
• Visit Piazza del Campo
• See Siena Cathedral
• Walk historic streets and shops
• Stop at Monteriggioni village
• Explore San Gimignano towers
• Visit Dondoli ice cream shop

Top questions

How long does this private day trip from Florence last?

The tour lasts around 8 to 9 hours including travel time between stops.

Is lunch included on this tour?

Lunch at an organic winery is available as an optional add-on for an extra fee.

What cities are visited on this day trip?

You’ll visit Siena, San Gimignano, and Monteriggioni (unless you choose the winery lunch option).

Is hotel pickup included?

Yes, pickup and drop-off at your selected hotel or address in downtown Florence are included.

Are wine tastings part of the experience?

Yes, there’s an option to taste craft Chianti Classico wines at a local vineyard during lunch.

Can dietary restrictions be accommodated?

Yes, vegetarian options or special diets can be arranged if requested when booking lunch.

How many people can join this private tour?

The experience is for your private group only (up to 7 travelers).

Is there free time to explore on our own?

You’ll have free time in both Siena and San Gimignano to wander or shop as you wish.

What’s included

Your day includes private transportation by air-conditioned Mercedes minivan with WiFi and unlimited cold mineral water, plus hotel pickup and drop-off in Florence. You’ll have free time in both Siena and San Gimignano; if you opt for lunch at a local winery, it features multiple courses paired with regional wines before heading back home in comfort.