My Favourite Tuscan Hilltop Towns So Far

Friday, June 24, 2016

My Favourite Tuscan Hilltop Towns So Far

Posted by Kiri 24/06/2016

When planning our trip to Tuscany, I wanted to make sure we had enough time to visit as many hilltop tops as possible. Tuscany is known for its awe-inspiring medieval hilltop towns that captivate visitors to the region. Sadly as we only had a week, we couldn’t fit as many as we wanted in, but there’s always next time. These are some of my favourite hilltop towns that I have seen so far.

We really fell in love with Lucca. It’s quite different to the other towns as it doesn’t seem as high up, and it’s enclosed by impressive walls that are distinctively different to the walls of other towns. One of my favourite memories from the entire holiday was simply cycling our retro bikes around the walls of Lucca.

Look in towards the city and you get a sneak peek of what’s inside, and look out into the distance and you can enjoy views of the surrounding mountains. It was so relaxing cycling in the sunshine and watching the locals walk their dogs around the path that runs round the city. There’s lots of restaurants and cafes to sample, a little stream runs through the city and there’s lots of shops selling local souvenirs including olive oil, which Lucca is famous for.

I had heard a lot about the infamous San Gimignano. It’s a well-known hilltop town that attracts a lot of tourists, and for good reason. It should definitely be on your Tuscan hilltop town to do list. You will gain an appreciation for San Gimignano as soon as you spot it in the distance, it looks rather magical from afar. I would recommend arriving early in the morning as we got there at lunch time, and there was traffic going into the town, if you go early you are more likely to get a parking space.

I think the most memorable part about this hilltop town was the architecture and the way the city is laid out. It feels like you are inside castle walls as you make your way along the narrow cobbled streets. Like many other hilltop towns, the views here are incredible. Make sure you wander to the viewing point and take a few photos. There’s lots of shops selling everything from wine and Italian meat to all kinds of pasta and sweet biscuits. Make sure you check out the The Duomo di San Gimignano, an impressive 12th century church.


Radda would definitely make our top three, mainly because it seems less tainted by tourism than some of the more well-known towns. It’s refreshing and unique, and the views here rival some of the best in the region. All the restaurants, bars and shops appear to be locally run with fresh local produce.

Bar Dante, on the corner of the town is a great place to relax and enjoy a spot of people watching. We grabbed pastries and coffee here a few times. Radda also has an art gallery in the centre, a spa if you fancy a cheeky treatment, a few wine shops where you can samples the wines and a good selection of restaurants.

Montalcino is home to the famous Brunello di Montalcino wine, one of the most expensive reds in Tuscany. We stopped here on the way back from the natural thermal spa at  Bagni San Filippo. We parked our car and walked to the top of the steps where there were stunning views of the hills and mountains, it was quite spectacular. Montalcino is a fairly small hilltop town, and good place to stop off. We stopped here for some lunch and to try some Brunello wine. 



The main reason Castellina is getting a mention is because we found the best ice cream shop in the entire world (no exaggeration) here. The lovely people at To Tuscany had recommended the new ice cream shop here, and when we arrived, we weren’t disappointed. It was the most delicious ice cream I have ever tasted, hands down.


The shop is located just outside the town (a five minute walk). Castellina is similar to Radda in that it’s quite a local town. There’s a few restaurants, shops and bars to enjoy, and the usual jaw-dropping views that many of these hilltop towns offer. 

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