The Most Breathtaking Hilltop Towns in Tuscany

Tuscany is well known for its stunning hilltop towns and incredible countryside – and this is why you just can’t miss out on exploring this side of the beautiful Italian region.

With each area offering something unique to see and do, you’re bound to find a town that has something that’s just right for you; whether you’re hoping to learn more about the Tuscan lifestyle, or just have a relaxing break from the stress of ordinary life.


If you’re looking for a great place to enjoy a traditional Tuscan meal or delicious wine, you may want to pay a visit to Montepulciano. There are a number of excellent vineyards to peruse, which are certainly worth a mention for anyone who’s interested in learning more about the wines that are produced here.

Exploring the town is also a great idea – in most cases, it can be easy to spend a few hours just wandering around the streets and taking in all the beauty.

San Gimignano

San Gimignano is one of the better known tourist spots in Tuscany – and with the amazing medieval architecture to be found here, it’s not hard to see why. There are plenty of things for you to see and do, so whether you’d prefer to climb the steps of Torre Grossa (the tallest medieval tower in the town), or sit back and enjoy a glass of Vernaccia di San Gimignano (made from grapes sourced from only the best San Gimignano vineyards); there’s likely to be something for you to enjoy.


There’s so much to love about Pienza – which is one of the main reasons why this town is such a popular tourist destination. At Palazzo Piccolomini, you could take in the scenery or check out the stunning Duomo. On the other hand, there are a few incredible museums in Palazzo Vescovile that are simply waiting for your attention.

If you’re thinking of perfect, peaceful vacations in Tuscany, Pienza is certainly worth a visit.


Brunello di Montalcino, one of the world’s best wines, is produced here in the small hilltop town of Montalcino, which alone is often enough reason to pay this part of Tuscany a visit.

Many people also stop by for Montalcino’s beauty, as it’s one of the most stunning medieval towns in the region – most notable for the large walls encompassing the town.

Why choose Tours of Tuscany?

Our team is well known for providing excellent tours around Tuscany – which is why we’re sure that you’ll enjoy your time with us. We offer a variety of options for you to choose from, so whether you want to go on one of the best San Gimignano tours available or have a relaxing Italian getaway, we’ve got you covered.

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