Departing from Florence you'll head south into the heart of Tuscany and the beautiful medieval city of Siena. The journey will last around an hour and a half, passing through the Tuscan countryside along a main road. A living testament to Italy’s medieval past, Siena is a wonderful showcase of gothic architecture, from the intricately beautiful Duomo with its elegant striped bell tower to the stunning red-bricked Piazza del Campo and grand Palazzo Comunale (town hall). The historic central area is a UNESCO World Heritage Site and Siena is considered to be Italy’s best preserved medieval city.
You will meet your private guide on arrival into the city and spent the next three hours exploring the charming cobbled streets and experiencing the authentic side of Siena. The tour will take you to the Duomo, famous for its gothic carved marble façade and pavements. You'll also visit Il Campo square where Siena’s bareback horse race, the Palio, is held every year. The square is also home to the imposing Palazzo Comunale. While walking from place to place, your guide will explain the city’s notorious contrada system which still wields an important influence on daily life.
After exploring Siena, you will continue on with your driver toward San Gimignano to stop in the countryside for a traditional Tuscan farmhouse lunch, paired with local wines. After lunch you will head into San Gimignano itself where you will have some free time to explore. Perched in typical Tuscan style on top of a hill, the village is dominated by a forest of 12th and 13th-century towers — built by wealthy families within the village as competing symbols of their wealth. At its peak, San Gimignano is thought to have boasted some 72 towers, though just 14 remain standing today. As well as the 12th-century Duomo, the pretty medieval streets are lined with many speciality food shops as well as small piazzas where you can enjoy a coffee or gelato and soak up the charming atmosphere and stunning views.
In Siena, ask your guide to point out Nannini, one the city’s best bakeries, famous for its typically Sienese ‘Ricciarelli’ biscuits. Equally, if you are touring with children, you can spend time with your guide searching for the tell-tale signs dotted around the city indicating the boundaries between the different contradas.
When exploring San Gimignano, a popular option is to climb the Torre Grossa attached to the 12th-century Pallazo Comunale for some spectacular views of the surrounding landscape. There are 218 steps to reach the top and your ticket will also include entrance to the civic museum. Alternatively, if you don’t fancy paying the entrance fee or if there's a large queue to climb the tower, we recommend heading up to the Rocca di Montestaffoli (signed simply as the ‘Rocca’). Accessed from the top of the Piazza delle Erbe, the small park contains the ruins of what was once a Florentine fortress, complete with a small tower that can be climbed for free. It offers equally stunning views across the surrounding countryside and olive groves below.