In the collective imagination, Tuscany is characterized by green hills fringed with cypress trees and medieval hill towns on the top. It’s a realistic image, even though Tuscany is much more than that: beaches, mountains, hidden corners and famous art towns and cities.
But the question is: if I have only a few days to visit Tuscany’s hill towns, how do I choose the best ones? Here’s a list of the top 10 hill towns in Tuscany, selected from the many gorgeous medieval villages that dot our countryside.
All these scenic hill towns boast fantastic views, charming old streets, great museums and plenty of history to tell. They are often surrounded by thick defensive walls and vaunt ancient gates and watch towers. These villages are often rich in art, too.
And now the list... choosing just 10 Tuscan hilltop villages was no easy task!
Anghiari is located in the Tiber Valley or Valtiberina, just 30 kilometres from Arezzo. It is considered to be one of the “most beautiful villages in Italy” and boasts the Orange Flag award from the Italian Touring Club. It is known for the famous Battle of Anghiari that took place here in 1440, which saw the victory of the Florentine troops against the army from Milan.
Leonardo da Vinci depicted this battle in a fresco in Florence's Palazzo Vecchio, but unfortunately it was lost after it was painted. Admire Anghiari’s strong 13th-century walls and get lost in its narrow, quaint streets with flowers on the houses’ balconies. Read also: Anghiari: 5 photos and 5 things to know.
Cortona is a hilltop town “under the Tuscan sun”, because it’s where Francis Mayes set her bestseller (“Under the Tuscan Sun”, indeed). It’s located in the Valdichiana or Chiana Valley, near Arezzo. From the hilltop there are splendid views over the surrounding valley with its cultivated fields and you can also see Lake Trasimeno.
Even though Cortona is quite small, it boasts beautiful churches and museums featuring Etruscan and Renaissance artefacts. Start your visit in Piazza della Repubblica, where the Palazzo Comunale stands, and continue with the Diocesan Museum (with the painting of the Annunciation by Beato Angelico) and the MAEC (the Etruscan Academy Museum of the City of Cortona). Looking for other places to visit? Head to the Girifalco Fortress and the Franciscan hermitage Le Celle, just outside the town.
When you see it from a distance, Pitigliano looks like a painting, with its houses perched on a spur of tuff. Pitigliano is a stunning medieval town in the Maremma area of Tuscany, also known as Piccola Gerusalemme, or “Little Jerusalem”. This area has been inhabited since Etruscan times and from the 1500s onwards, Pitigliano greeted a growing Jewish community (hence the nickname “Little Jerusalem”).
The town is quite small, so you can take a walk and visit the picturesque medieval centre, the Jewish ghetto with a small museum and the restored synagogue, and the narrow streets. Read also: A day trip to Pitigliano in the heart of Maremma.
Poppi is located between Florence (about 40 km east) and Arezzo (about 30 km northwest), in the Casentino area and is considered as one of the most beautiful towns in Italy by I Borghi più belli d’Italia. The town is a part of the National Park of the Casentinesi Forests, Monte Falterona and Campigna. The 13th-century castle of Conti Guidi crowns Poppi.
Inside this castle there’s a beautiful courtyard, a staircase, a library full of medieval manuscripts and a chapel with frescoes by Taddeo Gaddi. Don’t miss the Camaldoli Hermitage, the ancestral seat of the Camaldolesi monastic order. Read more here: Poppi: the walled city with a wonderful castle in the Casentino area.
Pienza is a tiny Renaissance gem nestled in the scenic hilly landscape of the Val d’Orcia, in southern Tuscany. With its special architecture, it was designed as a utopian city of the Renaissance by the humanist Pope Pius II. The cathedral and old papal residence in the Palazzo Piccolomini stand on the town’s central square called Piazza Pio II.
The town is a UNESCO World Heritage Site since 1996. Read also: 5 reasons to visit Pienza in Tuscany.
San Gimignano is not to be missed. About midway between Siena and Florence, San Gimignano was a natural stop for pilgrims walking to Rome. It can be considered one of the best preserved medieval towns of all Italy. Thanks to its appearance with high medieval towers, it has earned the nickname “Tuscan Manhattan”. Start in Piazza della Cisterna, then climb the Torre Grossa and visit its Civic Museum.
Head to the Collegiata (Romanesque ex-cathedral), the Church of Sant’Agostino with a wonderful 15th-century fresco cycle by Benozzo Gozzoli and, if you are brave enough, the torture museum. Read also: San Gimignano 1 day itinerary.
Montepulciano crowns a ridge with wonderful vistas of the Tuscan countryside, near Pienza. It stands on a limestone hill, 605 metres above sea level; it is one of the most beautiful medieval Tuscan towns and is called the “jewel of the 1500s” due to its impressive Renaissance art and architecture.
The central point of the town is Piazza Grande, which boasts the great tower and Gothic façade of the Palazzo Comunale (Town Hall) and the Cathedral of Santa Maria Assunta, which dates to 1619. Read also: A day trip to Montepulciano.
A little off the beaten path and surrounded by thick walls and hills that appear to be made to measure, Volterra has a long Etruscan history and affords interesting sightseeing. It is located between the valleys of Cecina and Dell’Era on a hill 1770 feet above sea level. Don’t miss the heart of the medieval town, Piazza dei Priori, with the wonderful Palazzo dei Priori, now the city hall, and Palazzo Pretorio, whose tower is traditionally known as the Tower of the Little Pig. Visit the Romanesque cathedral and its baptistery.
The Roman amphitheatre and the Guarnacci Etruscan Museum also deserve a visit. In recent years, Volterra has attracted international attention for its connection to the Twilight series of books and movies. Read more here: Things you can't miss in Volterra.
Monteriggioni, near Siena and Colle Val d’Elsa, is set atop a hill and is one of the best preserved walled towns in the world, maintaining its medieval structure as if time had never passed. Monteriggioni has a castle that was built for defensive purposes by the Sienesi between 1214 and 1219. It is referenced in Dante Alighieri's “Divine Comedy”.
The roughly circular walls presents 14 towers that can be seen from a distance. The main piazza is the Piazza Roma and is dominated by a Romanesque church. Walk in the narrow streets and breath in the Middle Ages. Read more here: Monteriggioni: a Tuscan jewel on the Via Francigena.
Montalcino is a hill town located to the west of Pienza, close to the Crete Senesi in Val d'Orcia around 40 kilometres from Siena. Enclosed by huge 13th-century defensive walls and characterized by a striking, perfectly preserved castle and fortress, Montalcino has remained practically unchanged over the centuries.
Montalcino is a special destination for wine lovers and it’s possible to do wine and food tasting in delightful cantinas. It boasts a striking 14th-century castle, encircled by olive groves and majestic vineyards. Read also: A day trip to Montalcino.