Private Siena, San Gimignano & Chianti Tour from Florence

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Free cancellationTravelers' pick

1/23

Duration8h

GroupPrivate

PickupAt your hotel

What makes San Gimignano's tower houses stand out after six centuries?

You get picked up at your Florence hotel and driven through the Chianti wine region to Siena, where you see the Piazza del Campo and the cathedral, then either stop at Monteriggioni or take lunch at a farm with wine tasting, then finish at San Gimignano's medieval towers before returning in the evening. Everything is arranged — the route, the timing, the driver who knows the history — so you just show up and look out the window.

Step-by-step itinerary

Explore Siena, Chianti, and San Gimignano

Drive through Chianti hills
Stop for pictures in Chianti
Visit Siena Piazza del Campo
See Siena Cathedral
Shop local food and gifts in Siena
Optional lunch at farm or winery
Visit San Gimignano medieval towers
Return to Florence

The Experience

"So we're actually driving through the vineyards?" That's what most people ask when the car pulls out of Florence heading south toward Siena. Yeah, you are — the whole Chianti region rolls past the windows, and your driver knows it well enough to point out which hills produce what, or just let you sit quiet with it. The private day trip from Florence covers serious ground in eight hours: Siena first, then the Chianti countryside, then San Gimignano perched on its hilltop like something from a fever dream. It's the kind of itinerary that sounds packed until you're actually there and realize the driving time between stops is half the experience.

Siena hits you with the Piazza del Campo first — that shell-shaped plaza where the Palio horserace happens every summer, and where locals have been gathering for seven hundred years. The 13th-century cathedral sits nearby, all striped marble and weight. Your English-speaking driver stays with the car, but they've already told you what to look for, what the streets are called, where the light hits best. After Siena, if you skip lunch, you can swing through Monteriggioni, a fortress town so perfectly preserved it looks staged. If you want to eat — and the description really does recommend it, especially if you care about wine — the tour can arrange lunch at a working farm or winery instead, which means you trade one of the towns for a proper meal and tasting. That's the trade-off, and it's worth thinking about before you book.

San Gimignano is the last stop, and it's the one people remember. Medieval towers rise from the hilltop like a skyline from 1300, and the town has barely changed since then. You walk the narrow streets, see the Basilica of Santa Maria Assunta, buy something you don't need from a shop that's been there for generations. By the time you head back to Florence, you've seen three different Tuscany — the urban medieval, the rural wine country, the hilltop fortress — and your driver has been talking the whole way about what you're looking at and why it matters.

The car is air-conditioned, the water is cold, and the pickup happens at your hotel. Maximum seven people per booking keeps it actually private, not just a small group tour. If you're traveling with kids, infant seats are available. The whole thing is eight hours door-to-door, which sounds long until you realize how much ground that covers and how little of it you have to navigate yourself.

What’s included

Your day includes hotel pickup and drop-off in Florence, transportation in a private air-conditioned car or minivan, an expert English-speaking driver, bottled water, and onboard Wi-Fi on request.
Optional farm or winery lunch with wine tasting can be arranged and is paid on site.
Entry fees to attractions are not specified in the itinerary.

Good to know

Easy physical levelStroller friendlyInfant seats available

Operated by Chianti Drivers private tours

Is this one for you?Book this if you want to see three major Tuscan towns and the Chianti countryside in one day without renting a car or planning the route yourself — the private driver and fixed eight-hour schedule handle all the logistics, leaving you to focus on what you're looking at.