Biking between hilltop villages in Tuscany

Biking between

hilltop villages in Tuscany

View of Montepulciano

This was without doubt our best day in Tuscany! Biking from one hilltop village to another was very relaxing and exciting at the same time. Most of our bike tour was on unpaved roads and the distance between the hilltop villages is about 5-8 kilometres. Best time to bike in Tuscany is in April-May and September-October.


Starting/Finishing point



30 kilometres

Length of time

3-6 hours



Water on the way

Yes, in the hilltop villages


On one day we had well enough time to visit three hilltop villages: Pienza, Monticchiello and Montepulciano.

Lupaia hotel where we stayed at has two mountain bikes that you can borrow for free and two electric bikes that come with a small cost. We planned to go by bike for 30 kilometres and then the mountain bikes worked just fine. You can also rent bikes in Montepulciano.

Starting at the hotel our first stop was the hilltop village of Pienza, famous for its Pecorini cheese. Pienza is also a UNESCO world heritage.

Biking to Pienza from our hotel took us about 30 minutes along a partly unpaved, partly larger road for 9 kilometres. There were almost no cars on the unpaved road but a bit trafficked when we reached the SP146.

Arriving in Pienza we locked our bikes just outside the centre of the village and walked through the village. From the Via dell´Amore you have a stunning view of the landscape and it is so silent you can hear the wind.

Pienza is a really lovely village so take your time passing through the narrow cobbled streets.

We then continued to the next hilltop village that could be seen from Pienza – Monticchiello - 6 kilometres away. From Pienza, take the unpaved road to Monticchiello. It is a bit tricky to find the start of the road but it is just outside the walls of Pienza from where you see Monticchiello far away.  

Monticchiello is on a very high hill, so we walked with our bikes to get to the top. Luckily there is a café and restaurant in Monticchiello so we had some coffée and ice-cream before continuing to the last hilltop village Montepulciano, 8 kilometres  away.

Montepulciano is just as lovely as the other villages and a little bigger - perfect for a lunch break. There are several restaurants to choose from, all just fine.

There are a lot of tourists visiting Montepulciano arriving by car. One great thing to go by bike here is that it is supereasy to find a parking for your bike! That is definately one reason to why it is so realxing to go by bike.

After having lunch in Montepulciano we biked down the unpaved road all the way to our hotel for the last 5 kilometres.

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