We spent a couple of days of our Tuscany holiday exploring the incredible hill towns. On one day we visited Montalcino, Montepulciano, Pienza and on the other San Gimignano and Certaldo Alto. We also visited the Abbey of Monte Oliveto Maggiore, a working Benedictine monastery. Montalcino, Montepulciano and Pienza are set in the beautiful Val d'Orcia valley. You can easily visit all three in a day as they are in close driving distance from eachother. They all have stunning views of the valley and lots of churches, little squares and palaces to explore. Montalcino is famous for it's Brunello red wine. San Gimignano is an enchanting and charming little medieval hilltown. It has 14 medieval towers rising above the town. The little duomo is definitely worth visiting. It is very unassuming but as soon as you enter you are surrounded by the most fantastic colourful frescoes covering all the walls. There is also a famous ice-cream shop in the piazza called Pluripremiata. You will have to queue but it is worth it! When we visited Certaldo Alto there was no-one else there... it was like it was completely deserted! We only knew about it as the people at our agriturismo told us it was worth visiting and it was. You can only get to it by parking in Certaldo Basso and catching the funicular up.