• San Gimignano and Siena tour
  • Siena and San Gimignano tour
  • Siena and San Gimignano tour
  • Siena and San Gimignano tour
  • San Gimignano and Siena guided tour
  • San Gimignano and Siena tour
Small-group (Up to 16 people)

Small-group Siena and San Gimignano Tour with Dinner from Florence

Discover the beauty of UNESCO-listed Siena, San Gimignano, and the Chianti countryside on our small-group tour from Florence. Watch the sun set over the vineyard-covered hills, and enjoy a traditional Tuscan dinner and a guided cellar tour at a local Chianti winery.  


About this tour:

8 hours
Live tour guide
Our expert guides selected for you
Personalized attention
Experiences designed for your needs
Free cancellation

Flexible reservation

Instant confirmation

Guaranteed Departure

Likely to sell out

Limited availability

  • 8-hour small-group tour of UNESCO-listed Siena and San Gimignano, from Florence.
  • Take a guided walking tour of Siena, and learn the history of sites like the historic Piazza del Campo.
  • Enjoy free time to explore the hilltop village of San Gimignano at your leisure, and admire its striking skyline.
  • Savor a traditional Tuscan dinner in a Chianti countryside winery, with wines paired by the experts and a guided cellar visit.
  • Enjoy personal attention from your guide on this small-group tour, limited to 16 people, or upgrade to a private tour for a more intimate experience.

UNESCO World Heritage-listed Siena and San Gimignano are two of the brightest jewels in Tuscany’s crown, and this thrilling half-day tour takes in both – with round-trip transportation from Florence included. Explore medieval Siena on a guided walking tour, and gain insight into the history of must-see sites like the Piazza del Campo. Enjoy free time to wander around the hilltop village of San Gimignano, and soak up the atmosphere at your leisure. Your day ends with a traditional Tuscan dinner at a local Chianti winery, followed by a cellar visit. 

Travel in Comfort from Florence to Siena 

Begin your tour with a pickup in central Florence by comfortable air-conditioned minivan, and relax on route to Siena. On arrival, enjoy a guided walk tour of the historic city, and learn the secrets of top attractions such as the Piazza del Campo – where the famous Palio horse race takes place every year. Your expert guide will share the story behind the Palio, and the 17 medieval districts that historically competed against each other.  

Before leaving Siena, there will be a surprise food-tasting for you! 

Marvel at the Medieval Skyscrapers of San Gimignano 

Leaving Siena behind, our next stop is San Gimignano – a medieval hilltop village famous for its iconic skyline. There’s no direct train line to the village, and many people ask how to reach San Gimignano from Florence. Our tour whisks you there with ease, with free time to explore at your own pace. 

Wander along the ancient streets, admire the elegant Romanesque and Gothic architecture, and soak up the atmosphere at your leisure. Delve into the village’s history, browse traditional products, and you could even head to the top of one of the towers if you’re feeling brave. The scenic views are certainly worth it! 

Traditional Tuscan Dinner at a Chianti Winery  

Continue onward to a boutique winery nestled among the vineyards deep in the Chianti countryside. As the sun sets behind the rolling Tuscan hills, sit down to an unforgettable evening meal of seasonal delicacies, with wine pairings selected by the winery’s own experts. You’ll also have the chance to visit the cellars with your guide, where vintage Tuscan wines lie slowly maturing in their mighty barrels.  

When your time in the Chianti winery comes to an end, return in comfort to central Florence to conclude your tour.  


Important Information

Please note that Italy's law doesn't permit selling alcoholic beverage to teens under 18 y.o. so clients under this age will be served non-alcoholic beverages.
Please let us know in advance any special need or impaired mobility of the clients and we will do our best to accomodate them.

Rain Policy

This tour runs on rain or shine.


Return transport from Florence in comfortable minivan
English speaking driver/tour leader
Guided walking tour of Siena with professional guide
Surprise tasting in Siena
Visit of San Gimignano with free time
Typical Tuscan dinner in a boutique winery in Chianti
Guided visit of the winery cellars
Wine tasting

Meeting Point

  • The meeting point is in our booking office in Piazza Mentana 2red, Florence (opposite the Arno River).

Find here the details of the private tour for a more intimate experience.
private upgrade

Starting from


price per person