Some of the most picturesque biking in Tuscany is through the rolling hills of the Chianti wine region and nearby Siena. As you cycle these roads you’ll pass sprawling vineyards and medieval cityscapes as you make your way through the beautiful countryside. Travelers on our Tuscan Hill Towns by Bike vacation will enjoy spending two days in the region biking along wine roads and absorbing the culture and history of the area’s largest city, Siena—whose historic downtown is a UNESCO World Heritage Site that is also the venue for one of the world’s most famous horse races, the Palio.
Siena embodies medieval charm like no other city in Tuscany. Its early inhabitants indulged in their rivalry with Florence right into the area of urban planning. Throughout Siena’s history, they preserved their city’s Gothic appearance, which was mostly developed between the 12th and 15th centuries. During this period, Sienese painters like Duccio, the Lorenzetti brothers and Simone Martini influenced the course of Italian and, more broadly, European art. Architecturally, the whole city is built around one of Europe’s greatest medieval squares, the Piazza del Campo, which was created as a work of art that blends into the surrounding landscape. VBT travelers will attend a presentation about the Italian Renaissance, the history of Siena and of the Palio by a local art historian during our stay in Siena.
The Palio horse race, which has taken place twice a year since 1656, is held right in the middle of the Piazza del Campo. As the spectators gather in the center of the square, riders representing their home contrade—district—race around the enlivened crowd. There are historic alliances and rivalries between contrades, and epic street celebrations lead up to and surround the races. VBT travelers are likely to see some of the festivities and decorations surrounding this famous local event during the June 20th departure of the Tuscan Hill Towns tour.
Siena is also the starting point for one of the tour’s loveliest bike rides during which you’ll explore the Chianti wine region by way of the Via Chiantigiana, a panoramic road that runs along hillside vineyards and through the sleepy hilltop villages of Radda and Castellina. These towns are the heart of the original Chianti wine region that was created in 1716, before it was expanded to include more areas within Tuscany in 1932.
These are just some examples of the experience you’ll have on our Tuscan Hill Towns by Bike tour. To learn more about our Italian vacations, please click here. If you would like to reserve a vacation or speak with one of our Tour Consultants, please call 800-245-3868. They are available Monday-Friday from 8:30am to 6:30pm EST and Saturdays from 10:00am to 3:00pm EST.