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

Super well organized, everything was beautiful

Lourdes Mónaco

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

9.6

(1,285)

Gratis

Pisa, Siena & San Gimignano Day Trip

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Accademia Gallery Guided Tour

Meeting point

Piazzale Montelungo

Reviews of our customers

8.9

Excellent 753 Travelers·61 reviews

June 14, 2026
Lourdes Mónaco Franco
Guadalajara, Mexico
Super well organized, everything was beautiful
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May 28, 2025
Anonymous
Chile
Good alternative to visit new places in Tuscany, but there are two aspects that may be better: 1. It makes little sense to have the tour simultaneous...
As a couple
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November 12, 2023
Julia Binney
United Kingdom
This was a brilliant trip. Jacobi our tour guide was really good, informative and helpful. His commentary was excellent and all his instructions clear...
As a couple
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October 6, 2023
Anonymous
United States
Great day, and Vera was wonderful. We enjoyed all the stops. The extra time in Siena was great. The wine tasting experience was a nice experience and ...
With friends
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May 10, 2023
Valentina
Madrid, Spain
Ha sido una experiencia maravillosa! Nuestro guía jacopo y conductor genaro nos hicieron visitar los diferentes sitios de una forma muy bonita ️ Jacop...
As a couple
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January 4, 2023
Mariana Rasmussen
Buenos Aires, Argentina
Constantino was a great guide! He is very enthusiastic and apart he is great for historical data, he recommended some places to go. I extremely recomm...
Traveling solo
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August 14, 2022
Michalina
Poland
We really enjoyed this trip. Everything was organized well. Our tour guide, Antonella, was very experienced and she gave information in three differen...
As a couple
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August 19, 2019
Donald
Attard, Malta
Very well organised. Our guide, Valentina was exceptional and gave very clear directions, useful tips and interesting information all the way . The c...
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June 10, 2025
Adriana Quevedo
Lima, Peru
This tour was well organized, the guides were amazing, very kind. The wine tasting was A1!!! The bus was confortable and very clean. I just would hav...
Traveling solo
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May 14, 2025
Edith
United States
Todo fue maravilloso. Alex nuestro guía con mucha paciencia nos explicó al detalle todo nuestro recorrido muy al pendiente de cada persona. El servici...
With friends
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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.

8.9