Florence to Siena & San Gimignano: Medieval Towns & Chianti Views

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Free cancellationTravelers' pick

1/23

Duration9h

GroupUp to 50

LanguagesEN

Mobile ticketAccepted

Two Medieval Towns in One Day: Why Siena & San Gimignano Matter

You travel by private coach from Florence through the Chianti countryside to Siena, where you have 2.5 hours to explore Piazza del Campo and the Duomo on your own. Then it's another scenic drive to San Gimignano, where you spend another 2.5 hours wandering medieval piazzas and tower-lined streets before returning to Florence in the evening. An English-speaking guide handles transport and timing; you handle the rest. Optional audio guide in Siena and wine tasting available at booking.

Step-by-step itinerary

Florence to Siena and San Gimignano

Bus ride from Florence to Siena
Explore Siena for 2.5 hours
Travel through Chianti countryside
Explore San Gimignano for 2.5 hours
Return to Florence

The Experience

What makes you want to leave Florence for a day? Maybe it's the pull of somewhere older, quieter, somewhere the crowds haven't quite figured out yet. Siena and San Gimignano sit in that space — two UNESCO towns that feel less like museum pieces and more like places where people actually live, argue about football, and argue about the Palio. This full-day tour from Florence takes you through both in a single loop, with 2.5 hours in each town to wander as you choose. You're not herded through a script. You show up, the guide points you toward Piazza del Campo or the Duomo di Siena, and then you're loose in the medieval streets for as long as you want.

The drive between them is half the point. You'll roll through the Chianti countryside for about an hour — the real Chianti, not the tourist version — and see what the landscape actually looks like when nobody's performing it for a camera. Cypress trees, vineyards, olive groves, farmhouses the color of dried apricots. San Gimignano announces itself from miles away: a cluster of medieval tower houses rising out of the hills like something from a fever dream. Once you're there, Piazza della Cisterna and Piazza del Duomo are small enough that you can find them without a map, but intricate enough that you'll stumble into corners you didn't expect. There's gelato. There are artisan shops. There's the kind of quiet you don't get in Florence anymore.

The coach has Wi-Fi and USB charging, which matters if you're the type who needs to stay tethered, but honestly you'll probably just look out the window. The English-speaking guide is there for the drive and the logistics — they're not narrating your experience in either town, which is the whole reason you booked this instead of a walking tour. If you want more depth in Siena, you can add an audio guide when you book. If you want to taste Brunello di Montalcino and other Tuscan wines on the drive back, that's an upgrade option too. The base tour is transport, two towns, and your own time to fill.

Pickup is from Florence, and you're back by evening. It's a long day — the kind where you sit on a bus twice and walk through two towns and eat lunch somewhere you found yourself — but it's the kind of long day that doesn't feel rushed because nobody's checking their watch but you.

What’s included

Round-trip private coach transport from Florence with Wi-Fi, USB charging, and complimentary water.
English-speaking tour leader for the full day.
2.5 hours free time in Siena to explore Piazza del Campo, the Duomo di Siena, and medieval streets.
2.5 hours free time in San Gimignano to wander Piazza della Cisterna, Piazza del Duomo, and artisan boutiques.
scenic drive through Chianti countryside with vineyards and rolling hills. Optional audio guide in Siena and premium wine tasting (Brunello di Montalcino and other Tuscan wines) available at booking.

Good to know

Easy physical levelPublic transport nearbyNot for heart conditionsInfants must sit on laps

Operated by City Wonders Ltd

Is this one for you?Book this if you want to see two of Tuscany's most famous medieval towns in a single day without renting a car or arranging your own transport — the fixed schedule and small group size mean you get both towns and the Chianti drive without the logistics.