We had a great stay in Tuscany last August. Having our base at Hotel Relais il Chiostro, we had four marvelous days in and around Pienza.
We had done lots of research from home months before we arrived in Tuscany, and we found a company called Cicloposse that arranged cycling tours in the area. We did not want to go on a group tour though, so we e-mailed them and asked if it was possible to rent bikes and explore the area by ourselves.
Not only did they let us rent bikes, but they also gave us suggested routes to follow for all four days. The bikes where of great quality, we got brands like Cannondale and Pinarello. We visited places like Montepulciano, Montalcino and Radicofani, just to mention a few.
Make sure you are in good shape before you go cycling in Tuscany. There are more uphills to climb that you can ever imagine. But being able to see Tuscany in this way is absolutely recommended. There are so many narrow roads that are perfect for bike riding.
We spent the evenings in Pienza. The beautiful medieval town has many shops and restaurants. There are lots of tourists during day time, but most of them are only visiting during the day. The evenings are quiet and romantic.
Our Holiday in Tuscany was perfect, and we can't wait to go back!