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

Summary

Siena’s medieval streets, san gimignano towers and chianti vineyards all in one private tuscany day

You’ll wind through Tuscany’s hills with a local guide, exploring Siena’s lively piazza and cathedral before choosing between lunch at a Chianti winery or more time in medieval towns. From tasting almond cookies to hearing church bells echo in San Gimignano, this private day trip lets you slow down and just be part of it all—even if only for an afternoon.

What’s the experience like?

The first thing I noticed as we rolled out of Florence was the way the light shifted—softer, almost golden, even though it was barely 9am. Our driver (Paolo—he insisted we call him that) pointed out little things I’d never have caught on my own: old stone farmhouses tucked behind rows of cypress trees, the smell of fresh bread drifting from a village bakery as we paused for coffee. Siena came up suddenly—one minute countryside, next minute you’re walking on these worn cobblestones in Piazza del Campo. Paolo told us about the Palio horse race; he got so animated describing it that an old man nearby grinned at us like he knew exactly what Paolo was saying. I tried a tiny ricciarelli cookie from a shop near the cathedral—sweet and almondy, still warm somehow.

We had the option to stop for lunch at a winery or farm in Chianti (Paolo said “it’s worth it if you love wine”—I mean, who doesn’t?), but we decided to keep going so we could see Monteriggioni too. The drive through the Chianti hills felt like something out of a film—vineyards rolling past in every direction, sun flickering through leaves. We stopped for photos by a crumbling stone wall; my partner tried to pronounce “Monteriggioni” and Paolo just laughed and shook his head. There’s something about that kind of laughter that makes you feel at home even when you’re not.

San Gimignano was our last stop—those towers really do look like they’ve been frozen in time. Kids were chasing pigeons around the square while an older couple sat quietly on a bench eating gelato (I wanted to ask them which flavor but chickened out). The Duomo bells rang right as we left; it echoed down those narrow streets long after we’d started back toward Florence. I still think about that sound sometimes when I’m stuck in traffic back home—you know?

Step-by-step itinerary

Day 1 — Explore Siena, Chianti, and San Gimignano

• Visit Siena's Piazza del Campo
• See Siena Cathedral
• Shop and taste local food in Siena
• Drive through Chianti hills and stop for photos
• Optionally have lunch at farm or winery
• Visit San Gimignano's medieval towers
• Return to Florence

Top questions

How long is the private day trip from Florence?

The tour lasts approximately 8 hours including travel time between stops.

Is hotel pickup included for this Siena & San Gimignano tour?

Yes, hotel pickup and drop-off in Florence are included with your booking.

Can I have lunch at a winery during this Chianti day trip?

Yes, there’s an option to organize lunch at a local farm or winery for an extra cost paid onsite.

Are entry fees or meals included?

No entry fees or meals are included by default; lunch can be arranged separately if requested.

Is this tour suitable for families with children?

Yes, infants and small children can join; specialized infant seats are available on request.

How many people can book together?

A maximum of seven people per booking is allowed for this private tour.

Will there be free time in Siena or San Gimignano?

Yes, you’ll have time to explore both towns’ historic centers at your own pace during the tour.

What’s included

Your day includes hotel pickup and drop-off in Florence with an English-speaking local driver-guide, bottled water for the ride, Wi-Fi onboard if you ask ahead when reserving, plus travel by private luxury car or minivan through Tuscany’s countryside—all with flexible stops along the way depending on your pace and interests.