Tuscany is famous for its hills and scenic hilltop towns. From all-time favourite San Gimignano and Cortona to lesser known gems like Massa Marittima, Pitigliano and Anghiari, each one has its own distinctive atmosphere. Many of these places can be visited in a day from Florence or Siena, and are wonderful spots to spend some time filled as they are with Medieval details, boutique shops and cosy trattorias. Here are some of our top picks for your next trip.

The 12 most beautiful Hilltop Towns in Tuscany

1. San Gimignano

San Gimignano is, undoubtedly, number one on the list here. With its perfectly preserved historic centre, it is hands down the most famous hilltop town in Tuscany. It has a nickname that explains it all: “The Manhattan of the Middle Ages”. referring to the house towers that have made its silhouette so famous all over the world.

Their height made these 13th century tower houses more easy protect when enemies attacked. But it was also a show of wealth and power. 14 are still standing today and you can even climb one, the Torre Grossa, to sample a bit of realistic Medieval feeling. Despite being very popular with tourists, with plenty of souvenir shops and enotecas, it is still well worth a visit. A uniquely time travelling (sort of an) experience.

Siena – Siena is one of the most iconic towns in Tuscany. Technically a hilltop town but much larger and with a great deal to see – from its magnificent Duomo to Piazza del Campo with its distinctive gothic buildings. It is 45 kms. from San Gimignano and both these two places should feature on every Tuscany itinerary, time permitting. See our Insider’s Guide to the best of Siena.

=> Our favourite things to do in San Gimignano

=> Explore the hills and the Best Medieval towns in Tuscany: see Siena, San Gimignano & Monteriggioni on this Guided Full-Day Tour from Florence!

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San Gimignano’s famous silhouette

2. Volterra

Volterra is a jewel of Tuscany. It has everything you want in a Tuscan hilltop town and more. Less ‘touristy’ and arguably with a more authentic feel than San Gimignano, it’s one of our favourite spots in the region.

Surrounded by delightful countryside, Volterra boasts a gorgeous main square with the oldest town hall in Tuscany Palazzo dei Priori, some charming museums – including the fascinating Etruscan museum – and plenty of alabaster workshops to visit.

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Volterra – Image by @Skitterphoto on pixabay

3. Cortona

Cortona became ultra popular thanks to Frances Mayes’ book “Under the Tuscan sun” , which showed all the love she has for this charming town. Perched in a magnificent position on top of a verdant hill, it has a wonderfully authentic Medieval town centre and plenty of enticing shops. The main square is the perfect place to enjoy Medieval Italy in style. It’s a welcoming place with plenty of little corners to explore.

=> Check out the Top things we love to do in Cortona

=> Join a Cooking Class in Cortona and learn the secrets of Tuscan cuisine!

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Cortona

4. Anghiari

Anghiari is still a bit outside the main tourist track. As so it has the benefit of feeling completely authentic, friendly and relaxed. You’ll find a delightful historic centre, picturesque corners, quaint artisan shops and good food.

Not to mention a museum that Leonardo da Vinci’s fans shouldn’t miss, the Museo della Battaglia di Anghiari. The hilltop town of Anghiari is in the Eastern part of Tuscany, 30 minutes south of Arezzo.

5. Radda in Chianti

Radda in Chianti is the prettiest of all Chianti small town. Entirely devoted to wine, it has various enoteche to enjoy and views that embrace the endless expanse of the Chianti vineyards. There’s not much to see in terms of sightseeing, Radda is more a way of living, enjoying the Tuscan countryside and all the taste and scents of a town that once used to be the capital of the Chianti league. Every year in May, Radda hosts the popular and intoxicating Radda nel bicchiere Wine Festival.

=> Discover 3 Great Wine Festivals in the Chianti region!

=> Explore the Chianti with our One-Day Chianti Road Trip

=> Best Chianti Wine Tasting Tours in Tuscany

6. Monteriggioni

Monteriggioni is more a one-square hamlet than a town. Embraced by a perfectly preserved set of Medieval walls on a low round hill, this fortified village was built here by the town of Siena as a defensive outpost against Florence. Today you can walk along the walls, and visit the Armoury Museum and try on one of their collection of heavy Medieval helmet for size.

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Monteriggioni

7. Certaldo Alto

Certaldo Alto is a quaint small hilltop town half an hour from Florence. It has two streets but there’s still enough to see to spend half a day enjoying the sights, that include the house of Medieval poet Boccaccio and the handsome Palazzo Pretorio, plus a handful of shops and nice informal trattorie.

8. Pienza

Pienza is probably the most graceful of all of the hilltop towns in Tuscany. Poetic, delightful and idyllic. We love it partly because of its position, a crown on the scenic Val d’ Orcia hill, and its charming architecture. Visit the Palazzo Piccolomini to see how a Renaissance architect was trying to reach perfection by combining architectural design and scenic views. Don’t leave without having tried the famous local pecorino cheese.

=> Scenic drive around the Val d’Orcia

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Pienza, the Cathedral square

9. Montalcino

Montalcino is the other jewel of the Val d’Orcia, the scenic countryside south of Siena. It’s renowned for the locally produced wine Brunello di Montalcino, that’s prestigious and pricey. And the impressive Medieval fortress that dominates the town, that today has been turned into a very special setting for top-notch wine tasting experiences.

Enjoy a great Day Tour visiting 3 of the most impressive hilltop towns in Tuscany: Montalcino, Pienza, and Montepulciano where the delicious “Nobile di Montepulciano” wine is produced!

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Montalcino’s Fortress

10. Montepulciano

Montepulciano has a dashing looking main square that is been used in more than one film, including the second series of the Medici family. It’s a lovely town near Pienza – and the drive from the two towns is one of the best Tuscany has on offer.

Here the Nobile di Montepulciano wine is produced, and a visit to the town is not complete without some wine tasting in one of the historic cellars of the area.

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Montepulciano, Piazza Grande

11. Massa Marittima

Massa Marittima is lesser known than other Tuscan towns, but if you take a bit of time to explore it, you’ll surely fall in love with it. Being a bit out of the way, it hasn’t made it onto the main tourist circuit yet which has obvious benefits.

You’ll find a stunning Romanesque cathedral in the main square where you can relax at an open air table. There are a couple of museums and some great views from the top part of town that stretch to the sea. It’s the perfect destination for those who want to combine a beach holiday with a bit of Medieval sightseeing, as it is just a few minutes drive from the Follonica gulf.

12. Pitigliano

Pitigliano is one of the most impressive hilltop towns in Tuscany. Located in the Maremma on an outcrop of tufa rock, the sight is gorgeous and unique even by Tuscan standards. Not as ‘manicured’ as other towns mentioned here, but a quite magical place nevertheless.

With a long history that dates back to the Etruscans, it is a jumble of narrow streets and stone houses overlooking a green chasm. Surely one of the most distinctive sights in Tuscany.

=> Looking for the most picturesque village in Tuscany

=> Nature lover? Wine passionate? Art lover? Read our Tuscany itineraries made for your interests!

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Pitigliano