San Gimignano, Siena, Chianti & Monteriggioni Day Trip From Florence

We took the tour with Beatriz leading the way and Fredi as our driver, and it was a real pleasure. As we traveled from p...

Albert

Set off on a fabulous day trip from Florence and discover Siena, Tuscany’s medieval town, visit Monteriggioni with its fascinating landscape, followed by San Gimignano, famous for its white wine, and then go on a wine tasting in the Chianti region.

Details

Duration

10 hours 30 minutes.

Language

The activity takes place with a guide that speaks in English and other languages.

Included

Transportation by bus or minibus
English speaking host
Guided tour of Siena (depending on selection)
Winery visit with wine tasting and sampling of typical products

Not included

Lunch
Ice cream tasting
San Gimignano and Monteriggioni guided tour

Supporting documents

Electronic voucher. Have it on your phone.

Accessibility

Not wheelchair accessible.

Sustainability

All services meet our

Pets

Not allowed.

Frequently asked questions

If you have other questions, contact us

Free cancellation

Free cancellation up to 24 hours before the activity starts. Any cancellations after this or no-shows on the day will not be refunded.

Free Walking Tour of Florence

9.1

(9,589)

Gratis

Pisa, Siena & San Gimignano Day Trip

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Meeting point

Piazzale Montelungo

Reviews of our customers

8.8

Excellent 49,764 Travelers·5,430 reviews

May 9, 2026
Anónimo
Spain
Roberta was very attentive at all times, providing us with plenty of information about each site during the journeys. The time allotted at each locati...
As a couple
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July 10, 2026
Karmel Gutierrez Pujana
Bilbao, Spain
Well organized. I recommend skipping the guided tour in Siena and the lunch to have more free time to explore. The double-decker bus broke down—things...
As a couple
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October 12, 2026
Albert
Spain
We took the tour with Beatriz leading the way and Fredi as our driver, and it was a real pleasure. As we traveled from place to place, Beatriz explain...
As a couple
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October 11, 2026
Jose Luis
Mijas, Spain
The places are wonderful, but there's not enough time to enjoy them. Adding half an hour to each location wouldn't significantly lengthen the entire e...
As a couple
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October 9, 2026
Pascual
Puna Arenas, Chile
The tour of San Gimignano, Siena, Chianti, and Monteriggioni was fantastic from beginning to end. A very well-organized day that allowed us to discove...
As a couple
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September 27, 2026
Felisa Elvira Benito Garcia
Madrid, Spain
Very beautiful, I liked everything a lot, especially Siena. I would remove the winery and give more time to Siena. The guide was delayed and it was s...
With friends
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September 18, 2026
Alicia
Rosario, Argentina
Everything was excellent. The itinerary was very well designed, there was time to do many things! The lunch was very good, the guide in Siena was grea...
Traveling solo
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September 11, 2026
Pedro
Alcala De Henares, Spain
The excursion was truly lovely. The towns were beautiful. The winery and tastings were excellent. The restaurant recommended by the guide in Siena was...
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September 10, 2026
Ruben Garcia Perez
Cadiz, Spain
Very well organized, Chiara is a very good guide, attentive and friendly, always available to answer any questions. The guide in Siena was also excell...
Traveling solo
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September 9, 2026
Anónimo
Spain
Diana and Lyon were very kind and friendly. The tour went exactly as described in the booking. All the activities were very well coordinated and punct...
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San Gimignano, Siena & Chianti Day Trip

On the day of the activity, we'll depart from Florence to visit some of the most beautiful towns in Tuscany. Let's get started!

On this excursion, we'll have the opportunity to visit Monteriggioni, one of the most characteristic villages of the region, with its walls and defensive towers almost intact.

In Siena, we'll enjoy a guided tour. Famous for its numerous monuments of Gothic architecture, this medieval town founded by the two sons of Remus condenses the typical charm of Tuscany. We'll discover it by admiring the façade of the Palazzo Pubblico, the Piazza del Duomo and the exterior of the cathedral.

After the 1-hour guided tour of Siena, you'll have time for lunch and continue exploring Siena on your own. Another town we'll visit on this tour is San Gimignano, a small walled town of medieval origin.

We'll stop for approximately one hour and 15 minutes so that you can discover why San Gimignano is known as the “Town of Fine Towers” and was declared a UNESCO World Heritage Site in 1990. The 14 perfectly preserved medieval towers are the symbol of the ancient power of its inhabitants, as wealthy families competed to have the tallest tower.

The tour then continues around the Chianti region, an area full of vineyards and wineries, producing wine of the same name. The landscapes of Chianti are the most characteristic of Tuscany. In this beautiful location, we'll make a stop in a well-known local vineyard for a tasting of some local produce, charcuterie, oils, and of course the local wine!

The tour will come to an end in Florence after between 10.5 and 11 hours as we return to the departure point.

Options

When you make your booking you can choose between the following options for your excursion to San Gimignano, Siena and Chianti:

Tour with a guide in Siena: you'll have a guided tour of the city and also taste some wine and typical products of the area, the most complete option!
Tour without a guide in Siena: ideal for those who don't want to have a guide in Siena and for those who want to enjoy more free time. This tour also includes a tasting.

8.8