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

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.

Options for this experience

4 options

Transport OnlyGuide in English · 09:00Round-trip transport in a comfortable air-conditioned coach lets you explore Siena and San Gimignano at your own pace.

With Wine TastingGuide in English · 09:00Includes a Tuscan wine tasting, with round-trip transport to explore Siena and San Gimignano accompanied by a dedicated tour leader.

Wine Tasting & Audio GuideGuide in English · 09:00Add an audio guide to deepen your understanding of Siena's medieval landmarks. Choose the wine tasting option for round-trip transport to discover Siena and San Gimignano, led by a dedicated tour leader, with a Tuscan wine tasting included.

Private TourGuide in English · 09:00A nine-hour private day trip to Tuscany with an English-speaking tour leader, private van transport, free time in both towns and a premium Tuscan wine tasting.

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Days and timesEvery dayDeparts at 09:00

Book up to1h before

AgesAdult (15 and older) · Child (2 to 14 years) · Infant (under 2): free

GroupUp to 50

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Low physical effortPublic transport nearbyNot recommended with heart problemsInfants 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.

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Top questions

Can children come?

Yes. Ticket types: Child (2 to 14 years); Infant (under 2): free.

How long is the full day trip from Florence?

The tour runs the full day, with 2.5 hours in Siena and 2.5 hours in San Gimignano, plus drive time between Florence and each town. You'll be back in Florence by evening.

Is lunch included?

No. You have free time in both towns to eat where you choose. There are restaurants, cafes, and gelato shops in both Siena and San Gimignano.

Do I need to follow a guide around the towns?

No. The guide handles transport and logistics. Once you arrive in each town, you explore independently for the 2.5 hours of free time.

Can I add a wine tasting?

Yes. Premium wine tasting, including Brunello di Montalcino, is available as an upgrade option at booking.

Is an audio guide available?

Yes, an audio guide in Siena can be added when you book if you want more detail about the city's historic centre.

What's included in the transport?

Round-trip coach from Florence, Wi-Fi, USB charging, and complimentary water. The coach is private and shared with the small group.

Is this tour suitable for people with mobility issues?

The tour is suitable for all fitness levels, but it's not recommended for travelers with poor cardiovascular health due to the walking involved in medieval towns with hills and stairs.

Can infants come on the tour?

Yes. Infants are required to sit on an adult's lap during transport.

What language is the guide?

The tour leader speaks English throughout the day, excluding the transport-only option.

How many people are in the group?

It's a small group tour, though exact group size varies by departure date.