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.
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.
Details
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.
Meeting point
Piazzale Montelungo
Reviews of our customers
- June 14, 2026
Lourdes Mónaco Franco
Guadalajara, MéxicoSuper well organized, everything was beautiful
Is this useful? - May 28, 2025
Anonymous
ChileGood 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 coupleIs this useful? - November 12, 2023
Julia Binney
Reino UnidoThis 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 coupleIs this useful? - October 6, 2023
Anonymous
Estados UnidosGreat 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 friendsIs this useful? - May 10, 2023
Valentina
Madrid, EspañaHa sido una experiencia maravillosa! Nuestro guía jacopo y conductor genaro nos hicieron visitar los diferentes sitios de una forma muy bonita ️ Jacop...
As a coupleIs this useful? - January 4, 2023
Mariana Rasmussen
Buenos Aires, ArgentinaConstantino 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 soloIs this useful? - August 14, 2022
Michalina
PoloniaWe really enjoyed this trip. Everything was organized well. Our tour guide, Antonella, was very experienced and she gave information in three differen...
As a coupleIs this useful? - August 19, 2019
Donald
Attard, MaltaVery well organised. Our guide, Valentina was exceptional and gave very clear directions, useful tips and interesting information all the way . The c...
Is this useful? - June 10, 2025
Adriana Quevedo
Lima, PerúThis 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 soloIs this useful? - May 14, 2025
Edith
Estados UnidosTodo fue maravilloso. Alex nuestro guía con mucha paciencia nos explicó al detalle todo nuestro recorrido muy al pendiente de cada persona. El servici...
With friendsIs this useful?
