Tuscany’s Most Beautiful Hilltop Towns


Tuscany’s Most Beautiful Hilltop Towns

The gorgeous countryside and hilltop towns are some of the most iconic parts of Tuscany – so if you decide to visit this beautiful region for a holiday anytime soon, you may to want to check out at least one.

You may find that each has something unique to offer, and a variety of things to see and do. Whether you want to enjoy a spot of wine tasting at an authentic winery, or explore a medieval town and learn more about the location’s history; there’s likely to be something for you. If you take the time to explore one of these incredible locations and learn more about the Tuscan lifestyle, you won’t regret it.


Montepulciano is well known for the amazing food and drink made here, so if you’re looking for the best place to enjoy traditional Tuscan cuisine, this is the place to be. If you’re more interested in wine, the Montepulciano vineyards are considered well worth a visit.

You’re sure to enjoy spending some time in the town square, Piazza Grande, as there’s just so much beauty that you can experience just from taking a stroll through the streets.

San Gimignano

Most famous for its medieval architecture, San Gimignano is one of the most well known hilltop towns in the whole of Tuscany. Here, you could climb to the top of Torre Grossa and enjoy the incredible views, try Vernaccia di San Gimignano (a delicious white wine that’s produced exclusively in this region), explore the ruins of La Rocca di Montestaffoli and so much more.


Pienza has plenty to offer its visitors – which you’ll likely find out for yourself if you decide to stop by. If you choose to visit Palazzo Piccolomini, you could check out its incredible Duomo and enjoy the beautiful views of Val d’Orcia Valley. Alternatively you could spend some time in Palazzo Vescovile, which is well known for the great museums located there.

Overall, you’re sure to find that Pienza is a calm and peaceful town, ideal for those who want to relax and explore the beauty that makes holidays in Tuscany so special.


If you’re a wine connoisseur, you may to want to pay a visit to Montalcio. Why? One of the greatest wines in the world, Brunello di Montalcino, is produced here – so you could get the chance to enjoy this incredible beverage right from the source.

Aside from that, Montalcino is popular for being a beautiful medieval Tuscan town, surrounded by large walls that give it a very impressive aura.

Go on your very own Tuscan adventure

Our team here at Tours of Tuscany could help you to not only explore the beauty of these hilltop towns, but also introduce you to so much more. Whether you’d like private Tuscany tours from Florence, or small group tours of San Gimignano; we’ve got something for you.

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