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

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.  

There will be a surprise tasting at the end of Siena guided visit, or in San Gimignano, depending on the operational needs. This special tasting will give you the chance to savor a local delicacy, adding a delicious touch to your Tuscan adventure!

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.