If Tuscany is the heart of Italy, Siena is the heart of Tuscany. It’s truly a special place that is featured on almost every one of our Tuscan tours. Many itineraries include an overnight stay in this storied city so we’re going to share our top 5 sights in Siena to see while on a cycling vacation. There are many more than 5 spectacular sights to see but we narrowed it down to our favorites.


With a history that dates back to before the 13th century, it’s not hard to see why the piazza tops our list of top 5 sights in Siena to see while on a cycling vacation. The Piazza del Campo is the center of Siena and was once a medieval powerhouse. It is one of the most famous Italian public squares due to its unique shell-shaped architecture. The piazza is also the sight of many markets and town events like the Palio de Siena, a world-renowned horse race in the town center (more on that later).


The Torre del Mangia rises over 100 meters above the Piazza del Campo and provides spectacular views of the piazza and town. If you dare, you can climb all the way to the top of the tower and get outstanding panoramic views of Siena and beyond! The bell tower was built to be the same height as the bell tower in the cathedral to symbolize the equal power between the church and civil authorities. It’s well worth exploring when in Siena!


We’re cheating with this one. Adding the Cathedral of Santa Maria Assunta to our list of top 5 sights in Siena to see while on a cycling vacation is actually our way of encouraging you to visit four more sights. The Cathedral of Santa Maria Assunta is home to the Piccolomini Library, the Crypt and the Baptistry. All of which are not to be missed once you’ve arrived at the doors of this breathtaking church. These sights are all striking in their own ways. The cathedral’s striking marble rests in a striped white and dark green marble pattern. The floor is also stunning with different scenes depicted in stunning detail. The library and the crypt, located inside the church, are known for their frescoes painted by masters of the Renaissance. The baptistry, featuring a truly breathtaking baptismal font is also a must-see while visiting.


The Santa Maria della Scala is one of the oldest hospital buildings still standing in Europe. It was once a haven for the sick, abandoned children and the poor. It ran on donations from the wealthy citizens of Siena. The hospital isn’t in operation anymore but when you visit the site, you’re treated to a museum full of art that was commissioned in the mid 1330s. Frescoes and altarpieces depicting and honoring the life of the Virgin Mary are seen throughout and well worth the time it takes to stop and take in their beauty. 


To explain the Palio de Siena, we need to start with the contrades of Siena. Contrades are the way Italian cities are broken down, similar to the arrondissements of Paris. The 17 contrade in Siena are possibly the most famous in Italy because of their long and storied histories. They are also so well known because twice each year, the contrade race around the Piazza del Campo on horseback. Yes, representatives from each contrade in Siena, race three laps around the town center on a dirt course. It’s outstanding to witness in person and coupled with our other top sights in Siena, you’ll have a busy stay in this Tuscan town!

What do you think? Did we miss one? These are definitely just our top 5 sights in Siena to see while on a cycling vacation but you may have another choice once you fall in love with this romantic Italian town. If you’re inspired to a take a Tuscan bike tour, let us know! We’d love to curate a trip for you!

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