San Gimignano to Siena and Monteriggioni: 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.

Dominating a hilltop in the rich Tuscan lowlands, this walled city was built by the Sienese at the beginning of the 13th century to defend the Cassia Road, and the cities of the Val d’Elsa and Staggia. Today, the walls are still in almost their original condition, the only changes being when the towers were lowered in the 16th century, and in 1921, 3 of the towers were lowered to the same level as the walls. Today, visitors are still able to walk the walls, and a combined ticket includes access to the interactive Armoury museum. The Romea Gate opens up into the main Piazza di Roma, which was originally used as a large vegetable garden that provided food when the town came under siege. Facing the square is the Romanesque Church of Santa Maria Assunta, which is as old as the town itself.