Greatest Tuscan Hilltop Towns to Visit

When I spent a few weeks in northern Italy last summer, I made sure not to skip the country’s most beautiful region: Tuscany. During my four days in Tuscany—I had a rental car—I visited Pisa, Florence and Cinque Terre (which is technically not in Tuscany, but anyway…), and passed through and by several gorgeous Tuscan hilltop towns, the very characteristic that makes the region so famous. For more information about traveling in Tuscany, you can check out these articles on

I loved it. Whenever you’re visiting Tuscany, make sure to get yourself a car or motorhome rental. Cycling is another wonderful way of exploring the countryside, but because of the hilly nature of the region, you’ll need to be in shape to do that. Either way, you’ll want wheels. It’s the perfect road trip region.

I’ve already written about the above-mentioned Tuscan cities, so in this new post, I’d like to talk a bit about the best Tuscan hilltop towns.

Top 5 Tuscan Hill Towns

1. Volterra

Top 5 Tuscan Hill Towns: Volterra, Tuscan hilltop towns: Volterra cityscape, Tuscany
Volterra cityscape, Tuscany: Photo on Flickr by Maja & Marko / CC BY-NC-ND 2.0

Volterra is one of the less-famous Tuscan hilltop towns, yet it’s undeniably worthy of a visit. This town dates from as far back as the ancient Etruscans. Perched on a lone-standing hill—a rocky outcrop, rather—Volterra boasts some of the finest views in Tuscany. There are old and beautiful architecture, an atmospheric town square and many stores selling local products. A feature that makes this town unique is the so-called Balze of Volterra, a number of canyons and cliffs that surround the town and make the town even more impressive.

2. San Gimignano

Top 5 Tuscan Hill Towns: San Gimignano, Tuscan hilltop towns
San Gimignano: Photo on Flickr by Antonio Cinotti / CC BY-NC-ND 2.0

Without question the most well-known of all Tuscan hilltop towns, San Gimignano is the one town you should focus on if you’re time is limited. It’s one of the best-preserved medieval towns in Italy, famously characterized by its fifteen towers. Formerly an important stopping point among pilgrims on their way to and from Rome, San Gimignano is a walled town with plenty of gorgeous buildings. Its historic core is a UNESCO World Heritage Site.

3. Montepulciano

Top 5 Tuscan Hill Towns: Montepulciano, Tuscan hilltop towns
Montepulciano: Photo on Flickr by SantiMB.Photos / CC BY-NC-ND 2.0

Montepulciano is a spectacular—arguably the most impressive of them all—hilltop town in southern Tuscany. Montepulciano features a collection of old churches and striking Renaissance palaces. This is a town that belongs on any itinerary in Tuscany. It’s famous for its wines—the town even lent its name to the famous Montepulciano wine. Make sure to head to the top of the Palazzo del Comune at the Piazza Grande for a wide and breathtaking panoramic view of the surrounding valleys.

4. Pienza

Top 5 Tuscan Hill Towns: Pienza, Tuscany hilltop towns Val d'Orcia
Pienza, Val d’Orcia: Photo on Flickr by Giampaolo Macorig / CC BY-NC-ND 2.0

Situated in gorgeous Val d’Orcia, Pienza is a stunning Renaissance city. Just like in this list, in real life it also lies between the hilltop towns of Montepulciano and Montalcino. The town was designed by Pope Pius II and it stands out from the rest because of its incredible charm. Its entire historic town center was declared World Heritage by UNESCO.

5. Montalcino

Top 5 Tuscan Hill Towns: Double Rainbow over Montalcino, Tuscany hilltop towns
Double Rainbow over Montalcino: Photo on Flickr by Antonio Cinotti / CC BY-NC-ND 2.0

Another typical Tuscan hilltop town, Montalcino is encircled by huge fortified walls, boasts a castle and offers amazing views of the fields, vineyards and olive groves that roll their ways to the horizon in every direction. Additionally, Montalcino is also renowned for its wine production, Brunello in particular. Also, as an Italian town, Montalcino is dotted with excellent restaurants serving delicious Italian food.

About Bram


Bram is a Belgian guy who's currently living in the USA. For over four years now, he has been wandering the globe, with jobs here and there in between. So far, his travels have taken him to four continents and twenty-two countries. Bram likes to try different styles of travelling: from backpacker and adventurer to tourist and local, he has been all those stereotypes and probably will be many more in the future. You can follow his adventures on his travel blog, on Twitter and on Facebook.

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