5 of Our Favorite Tuscany Hill Towns

View of Montepulciano

The beautiful Tuscan town of Montepulciano

These days while we’re all dreaming of being able to return to Italy, there’s one place that’s especially good at capturing our hearts and imagination: Tuscany. Isn’t there just something magical about those picture-perfect landscapes of rolling hills dotted with villages, vineyards, and rows of cypress tress? To inspire your future travel plans and keep Italy close to your heart, we’re sharing 5 of our favorite hill towns in Tuscany. Leave a comment below with your favorite town in Tuscany!


Perhaps one of the most quintessential Tuscan towns, Montepulciano beautifully blends medieval elements with an elegant Renaissance style. In the historic center, stop to admire the Palazzo Comunale designed by Michelozzo, which might remind you of the Palazzo Vecchio in Florence. Of course, a visit to Montepulciano isn’t complete without trying the famous wines from the region like the Vino Nobile di Montepulciano DOCG. This entire area is perfect for wine enthusiasts and you can find out more with our 4 Itinerary Ideas for Wine Tours in Tuscany. For a truly unique experience, plan a visit to Montepulciano on the last Sunday in August for the Bravìo delle Botti festival. The 8 historic districts of Montepulciano compete in an intense challenge to roll 176-pound barrels uphill through town. Along with that unusual feat is a parade of historic costumed figures and flag throwers.

Where to Stay: Looking to savor those iconic postcard views of Tuscany’s rolling hills? Our lovely Borgo Beco is just one of the properties available on the Borgo estate surrounded by the unspoiled southeastern Tuscan countryside.

View of Monteriggioni in Tuscany

The medieval walled town of Monteriggioni (Credit)


In the rolling hills northwest of Siena sits a medieval marvel of a town called Monteriggioni. The surrounding hillsides covered in rows of grape vines and olive tree completes the idyllic scene. What makes this town especially unique is that it’s completely enclosed within 13th-century walls punctuated with 14 guard towers that form what looks like a crown from the hillside below. The impressive sight of Monteriggioni’s wall and towers was even mentioned by Dante in the Divine Comedy (Inferno, Canto XXXI, 40-44). Founded in the early 13th century, Monteriggioni was built by Siena as a defensive outpost against their rivals the Republic of Florence. Inside these massive wall is small medieval village full of charm. While visiting, don’t miss the chance to walk along the walls around Monteriggioni.

View of San Gimignano in Tuscany

San Gimignano with its famous towers

San Gimignano

Easily one of gems of Tuscany–if not all of Italy–the hilltop village of San Gimignano is easily spotted in the distance by its many stone towers. While the 14 towers in town seem like a lot today, it’s nothing compared to the town at the height of its glory when there were 72 towers in this small hilltop town! Each tower was part of a private fortified home, and its in impressive experience to imagine so much protection being required in the Middle Ages. San Gimignano is a UNESCO World Heritage Site with one of the best preserved medieval historic centers in Italy. Besides admiring the towers, plan to visit to the Collegiata, the Romanesque era ex-cathedral, to see the the incredible frescoes by Benozzo Gozzoli and Domenico Ghirlandaio. Next, stop by the Palazzo Comunale to see the collection of 13th-15th century art by Sienese and Florentine painters and to climb to the top of the 14th-century Torre Grossa for an unforgettable view overlooking the town and countryside. Given its remarkable history and beauty, you won’t be alone while visiting San Gimignano, but it’s an experience not to be missed in Tuscany.

View of Anghiari in Tuscany

The hilltop town of Anghiari (Credit)


As off the beaten path as San Gimignano is famous, the hilltop town of Anghiari is located about 16 miles east of Arezzo in the Valtiberina Valley. Considered one of the Borghi più belli d’Italia, or Most Beautiful Villages of Italy, Anghiari holds a good deal of fascinating history within its early 13th-century walls. With its strategic hilltop location and alliance with Republic of Florence in the 15th century, the fortified town was the setting for the intense Battle of Anghiari on June 29, 1440 between the Republic of Florence and the Duchy of Milan. The day-long battle was an important victory for the Florentines in Tuscany and was later the subject of a Leonardo da Vinci fresco painted for the Palazzo Vecchio in Florence. Unfortunately, the fresco did not survive due to Leonoardo’s experimental technique, but a later drawing by Peter Paul Rubens inspired by the fresco hangs in the Louvre Museum.

Where to Stay: Curious to explore this lovely part of Tuscany? Our Romanza Villa is located only about a 20 minutes drive south in the verdant countryside not far from where Tuscany meets Umbria. This 3-story stone villa is nestled in 2.5 acres of gardens and features a pool for complete relaxation surrounded by the beauty of Tuscany.

Piazza della Repubblica in Cortona

Cortona’s charming Piazza della Repubblica


This hill town hardly needs an introduction as it was firmly placed on the map as the setting for Under the Tuscan Sun by Frances Mayes. Located about 20 miles south of Arezzo, Cortona has a picturesque setting overlooking rolling hills with Lake Trasimeno in the distance. Although well known, the town is absolutely charming and offers a surprising amount of artistic richness in addition to its quaint piazzas and winding streets. Find a seat at a café in the town’s Piazza della Repubblica, with a striking staircase leading up to the Palazzo Comunale, and enjoy some fine people watching. Then stroll just a few minutes to the Diocesan Museum to see the remarkable Annunciation painted by Fra Angelico along with an excellent collection, including many works by Renaissance artist Luca Signorelli who was born in Cortona. Step further back in time at MAEC Museum of the Etruscan Academy and the Town of Cortona, which holds a rich archaeological collection from the Etruscan civilization. Very fitting for a city that is still protected by Etruscan era walls.

View of Florence from Fiesole

Spectacular view overlooking Florence from Fiesole

Bonus … Fiesole!

If you’re staying in Florence and want to get a taste of the Tuscan hill town experience but don’t have a lot of time, don’t miss a chance to visit Fiesole. Located just outside Florence and easy to reach by taxi or bus, this hilltop town was founded by the Etruscans and fortified in the early 14th century. With its fine views overlooking Florence, it was a favorite haunt of the Medici family and is home to the Medici Villa designed by Michelozzo and built from 1458 and 1461. From Etruscan ruins to an ancient Roman theater and refined 18th and 19th-century villas, Fiesole has more to offer than just panoramic views. Read more about Fiesole, the Crown of Florence.

Where to Stay: Everything we love about Fiesole is perfectly captured with a stay at our Divine Dante villa. Surrounded by peaceful gardens, this exquisite villa has an incredible history, with connections to the poet Dante Alighieri and later the family of Beatrice, the object of Dante’s desire and source of inspiration of Dante’s works Vita Nuova and the Divine Comedy.


Need help picking the most beautiful places to visit and stay in Tuscany? Get in touch with the Italy Perfect team and we’ll be happy to help you plan the perfect vacation rental for your trip.

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