Top 10 (+1) Tuscany’s hilltop towns and villages!

June 11, 2014
Enrico Catani

Regarded as the birthplace of the Renaissance, Tuscany is a region rich in history, art, culinary traditions and natural treasures. Abroad, it is mostly renowned for its Capital, Florence, but you’d make a huge mistake to miss the hidden gems dispersed in its spectacular countryside!
We are talking about enchanting villages with a medieval heritage, built upon the rolling hills that characterize the Tuscany’s landscapes.
Those small Tuscan hill towns still conserve the atmosphere of the past, and reveal to the visitors many surprises at every corner, not only because of their beauty, but also for their immense historic and artistic value.
And if you’re looking for a place to avoid the hectic pace of modern life and, at the same time, culturally enrich yourself, those medieval villages should be your next vacation destination! Furthermore, they are also home of the authentic, genuine Tuscan cuisine (a very good reason to take into consideration).
So, here is a list in no particular order, made by ItalyXP, of the ten (plus one!) hilltop towns in Tuscany that shouldn’t be missed from your itinerary!


Viewed from afar, Barga resembles a rock sculpture shaped by the wind, surrounded by green rolling hills. With its cobbled lanes, tiny squares and steep stairwells this hamlet out of time is considered an immaculate Tuscany’s jewel, still untouched by mass tourism.
The main point of interest is undoubtedly the imposing Cathedral (Duomo di San Cristoforo), founded around the year 1000, and whose interior houses marble statues of timeless beauty. In front of the Cathedral is the Arringo, a big lawn where the citizens used to gather in parliament in the past centuries and from which you can admire breathtaking views of the surrounding landscape


This walled town upon a hill in Northern Tuscany is permeated with a unique medieval and renaissance charm.
Volterra is famous for its famous tradition of carving alabaster, which is extracted in this area. You can book a guided tour to visit the traditional craft-shops where the famous “stone of light” is finely carved and refined, through an ancient process that boasts a centuries-old history. Also the beautiful stained glass of the Romanesque Cathedral is made in alabaster.
Most of Volterra’s buildings, towers and medieval walls are made of a yellow-gray colored stone, called “panchina”, that provides the city a magical, austere aura.
Many poets and artist have been inspired by Volterra’s landscape: more recently Stephenie Meyer, the author of the Twilight saga, who has set here the second episode, “New Moon”. For all the vampire fans, a Twilight Tour of Volterra is a must-do!

Best hilltop towns in Tuscany


This medieval village nestled in the Upper Tiber Valley, perfectly retained in its urban structure, is famous for its excellent level of livability and the welcoming, bucolic atmosphere.
Protected by its 13th century walls, Anghiari has been the site of epic battles and important historical events, whose traces are still visible in the historic centre. The countless handicraft shops and antique boutiques, established in the medieval streets, reveal the passion and the traditions of the inhabitants of Anghiari. Also, the active theatrical life and the numerous fairs and local festivals contribute to enliven the cultural life of this lovely town.

San Gimignano

Located in the province of Siena, San Gimignano is famous for its spectacular medieval architecture, in particular its 14 surviving towers (originally were 72) which have earned the town the nickname of the "Manhattan of Tuscany", because of the beautiful skyline they create.
Declared as World Heritage Site by UNESCO, the historic centre of San Gimignano is dotted with important monuments and several interesting museums, such as the Torture Museum! Also, there are many small taverns with medieval atmosphere where one can enjoy typical food accompanied by a glass of the Vernaccia white wine.
If you’d like to eXPerience a journey through nature, history and good white wine, San Gimignano is the ideal choice. And why not choosing a tour that includes the Chianti area… So that you don’t miss the opportunity to taste the Tuscan’s red wine too!

Best hilltop towns in Tuscany


Thischaracteristic town of the Maremma area is perched atop a ridge of tuff (a volcanic, porous rock consisting of consolidated volcanic ash). Its peculiar tower houses are built vertically on sheer tuff cliffs in which they seem like a natural continuation.
Besides its Etruscan origins, Pitigliano is also known as “Little Jerusalem” because of the Jewish community who settled here in the 15th century, whose traces are perfectly preserved in the picturesque Jewish Ghetto, where you can admire the Synagogue and the Jewish Cemetery.
The archeological sites around the town are among the most impressive in Italy. Travelers interested in archaeology shouldn’t miss a visit, while wine lovers will definitely enjoy the many excellent local wines, such as the Pitigliano DOC which is aged and kept in cellars carved in the tuff.

Best hilltop towns in Tuscany


Placed at the foot of the homonymous mountain, this ancient town is characterized by typical medieval traits, such as the reddish 15th century walls that surround it and the spiral urban structure that wind along the sides of the hill.
Besides the numerous religious buildings that preserve works of art of inestimable value, Cetona is renowned for the Prehistory Museum, which conserves the archaeological finds from the prehistoric settlements discovered during excavations in the area around Cetona. The museum is connected to the delightful Archeological Park of Belvedere: an uncontaminated natural area where visitors can admire prehistoric caves and settlements that go back 40.000 years.
Rather than walking around the area on your own, we highly recommend to arrange a guided tour, which would be more informative and will allow you to visit restricted sights.

Best hilltop towns in Tuscany


Located between Florence and Arezzo, the town of Poppi has many special treats for its visitors: restored villas and farmhouses, picturesque Tuscan landscapes and lots of culinary treats which are locally produced.
The main point of interest is the Castle of the Counts of the Guidi Family, an imposing 13th century castle that rises on a hill, dominating Poppi’s historic centre and the surrounding valley.
A peculiarity of Poppi is the presence of long arcades in the main streets, which make its architecture unique in Tuscany. Recently, it has been officially inserted in the “most beautiful villages in Italy”, because of its beautiful monuments and artistic wonders, such as the baroque church Oratorio della Madonna del Morbo.
This romantic town is the ideal place for an authentic, relaxing Tuscan vacation eXPerience!

Best hilltop towns in Tuscany


Perched on a wooded hill, the medieval town of Montalcino overlooks the exceptional landscapeof the Val d’Orcia countryside, from a height of 567 meters.
The Rocca, an imposing 14th century Fortress, dominates the historic-centre, whose architecture has remained intact over the years. Another remarkable attraction of Montalcino is the characteristic narrow tower of the Palazzo dei Priori (the town hall), located in the main square, Piazza del Popolo: from here, winds an intricate maze of alleys filled with craft boutiques, small cafes and traditional taverns.
There are lots of local products and delicacies one can taste in Montalcino, but above all the Brunello reigns supreme: one of the most prized and renowned wines in the world, the Brunello is an icon of this part of Tuscany. If you consider yourself a wine lover, a wine tour in Montalcino is an eXPerience you cannot miss.

Best hilltop towns in Tuscany


The town of Vinci owes much of its fame to the fact that it was the birthplace of Leonardo da Vinci, one of the greatest geniuses of all time, and whose name is inextricably linked to many places in Tuscany.   The memory of Leonardo da Vinci and its sensational inventions is still alive today in this lovely town, where you will be able to visit its birthplace-house, the "Leonardo da Vinci Museum", which collects projects and prototypes made by him, and the Leonardo Library.   Definitely worth a visit are also the historical centre that exudes a characteristic medieval atmosphere, and the surroundings of Vinci, surrounded by green rolling hills and beautifully cultivated vineyards.
If you're in Tuscany, do not miss a tour of Leonardo da Vinci birthplaces, to discover the history and secrets of this fascinating Italian scientist.

Giglio Castello

The fortified town of Giglio Castello is located upon the highest hill of the Giglio Island, offering a spectacular view of the Tyrrhenian Sea.
Giglio Castello, the oldest town in the island, is accessible through a picturesque, ancient port that, once crossed, reveals a magical world that exudes an air of heavenly tranquility and times past.
It’s a pleasure to explore the narrow alleys, surmounted by stone arches that create a play of light only, followed by the smell of the Mediterranean cuisine and with anendless panorama that surprises you at every corner.
The historic centre is dominated by the Rocca Aldobrandesca (medieval Fortress) and is enclosed by a curtain wall that have made Giglio Castello one of the most well-preserved villages of Italy.

Best hilltop towns in Tuscany


Seen from afar, the fortified town of Monterrigioni, with its 10 meters high walls alternated by 14 towers,gives the impression that time has never passed on the hill from which it imposingly dominates the surrounding land.
The perfect circular perimeter of its massive walls might make you suppose it to be an artificial construction, while actually it was created by just following the natural curvatures of the ground. Conceived as Siena’s defensive outpost for its strategic location, Monteriggioni has strikingly managed to preserve its urban structure and its ancient appearance over the centuries. Quoted by Dante Alighieriin his “Inferno”, the unique atmosphere of Monteriggioni has also been inspiration for the famed videogame Assassin’s Creed.
Known to be one of the best examples of medieval villages in all of Italy, there are few other places that were able to impress us so deeply! If you’re planning a trip to Tuscany it would be a terrible crime to skip a tour of Monteriggioni and its surroundings…

Best hilltop towns in Tuscany

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