Must Visit Hilltop Towns in Tuscany

by Tours of Tuscany
Must Visit Hilltop Towns in Tuscany

Must Visit Hilltop Towns in Tuscany

When most people think of the breathtaking Italian region of Tuscany, they’ll probably envision the beautiful hilltop towns and beautiful landscapes that it is so well known for. Because of this, vacations in Tuscany just aren’t the same without a visit to one of these stunning locations.

Each town and village is special in its own way, which is why you’re sure to enjoy your time here. From tasting some of the best wines in the world, to strolling through medieval villages; there’s just so much to love. If you’re hoping to immerse yourself in the Tuscan lifestyle or just want a relaxing holiday, you won’t regret a visit to one of these excellent hilltop towns.


If you’re looking for Tuscan cuisine at its best, a trip to Montepulciano should definitely be on your bucket list. From the amazing wines (made from grapes produced at local Montepulciano vineyards), to the many great trattorias and restaurants; fine dining is a must.

You could spend a few hours exploring Piazza Grande while you’re here – you’re sure to be mesmerized by the beauty of Montepulciano’s streets.

San Gimignano

San Gimignano is probably one of the region’s most well known hilltop towns. There’s just so much to love about this location; from the incredible medieval landmarks (such as Torre Grossa and La Rocca di Montestaffoli), to the friendly locals and stunning views.


Pienza is a popular tourist destination, thanks to the wide variety of things to see and do here. Many people choose to check out the stunning vistas and the Duomo in Palazzo Piccolomini, while others instead opt to spend time learning about the town’s history in one of the great museums in palazzo Vescovile.

If you’re looking for a good place to just sit back and relax, Pienza could be the ideal town for you.


One of the world’s greatest wines, Brunello di Montalcino, is produced right here in Montalcino itself, so if you consider yourself to be a fan of wine, you’ll have to pay this gorgeous hilltop town a visit.

That’s not all though – as Montalcino is also quite well known for its medieval beauty, which can easily be seen while strolling through the streets. The whole area is surrounded by large walls too, which only makes the town more impressive.

Explore the region with Tours of Tuscany

If you’re hoping to see all that Tuscany has to offer, we’re sure that our team will be able to help.  We offer some of the best day tours of Tuscany available, so regardless of how you want to spend your time here, we’ve got something for you (from exciting trips to San Gimignano, to Chianti wine tours).

Email Us