Cortona to Siena: Private day trip

The medieval city of Siena is most famous for the Palio, a bareback horse race that has been held in the city square twice a year since the 16th century. Outside of the race, the city is an alluring mixture of medieval architecture and Tuscan tradition. The main square is dominated by the early 14th century Palazzo Pubblico and its soaring tower. This historic building still houses the city's municipal offices, and welcomes visitors to learn more about the town's history in the Civic Museum. If you're up for a rewarding challenge, you can climb the 500 steps to the top of the tower for wonderful views of Siena and its surroundings. Also in the square is Siena's stunning Gothic cathedral, which is one of the finest in the country with its painted facade and interior filled with beautiful Renaissance frescoes. Of course, being in Tuscany, it's also a great place to sip one some wine and sample the region's cuisine.