The Top Ten Towns in Tuscany, Round II

We know that you have been eagerly awaiting the second half of our list of Tuscany’s ten top towns. We just know that you are eager to discover the next five!

So, here they are.


MontepulcianoPisa has the Leaning Tower, but that’s just one reason to visit. It is located about a half hour southwest of Lucca and was at its peak during the 11th-13th centuries. Pisa is still a medieval powerhouse thanks to its stunning churches, palaces, and streets. The Gioco dil Ponte is a series of medieval-themed battles that are held every year on the last Sunday in June. The Leaning Tower, meanwhile, is quite cool. Our tip: Visit the tower in the evening when the sun is setting, after all the tour buses have left, and you will have it almost to yourself.

Are you a wine-lover? This is a great addition to your list. Are you not a wine lover? You will become a wine-lover after you visit. The most famous thing about Montepulciano is Vino Nobile di Montepulciano. This DOCG-rated wine has been enjoyed since the Middle Ages, and is widely regarded as one of Italy’s finest. It’s possible to spend an entire afternoon wandering through the medieval streets of Montepulciano, taking advantage of the wine, meat, and cheese samples available in the shops. But don’t forget the beautiful palaces and churches that dot the town. You might be in good company if you spend all your time in a wine shop. Henry James said that he couldn’t recall details of Montepulciano because he had spent so much time drinking.


Montalcino is smaller than Montepulciano (at around 5,000 its population is approximately a third of Montepulciano’s). It is also less touristy despite its claim to fame: Brunello di Montalcino is often considered the best wine in Italy. The town’s most notable feature is its Museo Civico and Diocesano de’Arte Scra. It houses a wide variety of Renaissance and medieval works that are surprising considering the town’s small size. A magnificent 14-century castle is also available, complete with a park and a walk along the ramparts.


The town was used as the setting for Life is Beautiful scenes. You will see why when you visit Arezzo’s historic center. It is beautiful and unspoiled. The tranquility of this town hides a rich past, which included being one of the 12 Etruscan capitals, and then becoming a wealthy independent republic in the Middle Ages. It is now home to almost 100,000 people and is a popular spot for culture and art lovers. The Church of San Francesco in Arezzo has a large cycle of frescoes from Piero della Francesca (15th-century master). Vasari’s frescoes at Casa Vasari show an artist’s life, while the Archaeological Museum contains many ancient finds. It’s no surprise that Petrarch, “father of humanism”, was born in Arezzo in 1304.


Frances Mayes had written about her time in Cortona in Under the Tuscan Sun. Cortona, which is home to around 22,000 people, has become a tourist hot spot. That means day-trippers aplenty. We think the town is worth a visit for a day or afternoon, even though it’s located in middle Italy. These views are breathtaking, stretching from the dramatic hilltop town to the rolling countryside and Lake Trasimeno. There are many other worthwhile places, such as the Museo dell’Accademia Etrusca which is chock-full of ancient Etruscan treasures from the area.

Don’t forget the towns! Check out our video below of Tuscany’s beautiful countryside

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