The Top Ten Towns of Tuscany, Round II

Following the first half of our list of Tuscany’s ten best towns, we just know you’ve been waiting with bated breath to find out what the last five top towns will be!

And so, without further ado: Here they are.

Pisa

One of Pisa’s more famous sights

Yes, Pisa’s got the Leaning Tower — but that’s not the only reason to go. The city, a half-hour’s drive southwest of Lucca, reached the height of its dominance in the 11th to 13th centuries. Thanks to the stunning churches, palaces, streets and squares of the era, Pisa still feels like a medieval powerhouse today. Come on the last Sunday of June to see the Gioco del Ponte, a series of battles staged in medieval costume every year since at least the 16th century. And, okay, the Leaning Tower is pretty cool, too. Our tip: Come in the evening, as the sun’s just setting and after the tour buses have gone, and you’ll have the tower almost to yourself.

Montepulciano

Montepulciano… and its wine.

A wine-lover? Add this to the list. Not a wine-lover? After visiting, you will be. Montepulciano’s biggest claim to fame is its Vino Nobile di Montepulciano, a DOCG-rated wine that’s been consumed since the Middle Ages and is considered one of Italy’s best. You could spend a whole afternoon here wandering the small town’s medieval streets and taking advantage of the free wine, meat and cheese samples offered in the stores, but don’t miss the town’s smattering of lovely palaces and churches, either. Then again, if you do spend your whole time in a wine shop, you’re in good company: After Henry James left Montepulciano, he said he struggled to recall the details of the town… because he’d spent all his time drinking!

Montalcino

Montalcino, Tuscany

Smaller than Montepulciano (at some 5,000, its population is about a third of Montepulciano’s), Montalcino also is less touristy, even though its claim to fame is similar: It produces Brunello di Montalcino, often considered to be Italy’s best wine. Other than that, the town’s top boast is its Museo Civico e Diocesano d’Arte Sacra, with a wealth of medieval and Renaissance works surprising for the town’s size. There’s also a majestic 14th-century castle, still complete with a public park and walk along the ramparts.

Arezzo

Piazza Grande, the main square in Arezzo

This town served as the backdrop for scenes from Life is Beautiful, and when you come here, you see why: The historic center of Arezzo is lovely and unspoiled. Its tranquillity belies a powerful past that included being one of the 12 Etruscan capitals and then, in the Middle Ages, a wealthy independent republic. Now home to nearly 100,000, it’s a hot spot for art and culture lovers. Arezzo’s Church of San Francesco boasts a great cycle of frescoes by 15th-century master Piero della Francesca, Vasari’s frescoes in the Casa Vasari depict an artist’s life journey, and the Archaeological Museum displays numerous ancient finds. Perhaps it’s not surprising that Petrarch, the “father of humanism,” was born here in 1304.

Cortona

You can’t beat the views from Cortona

After Frances Mayes wrote about living here in Under the Tuscan Sun, Cortona, home to some 22,000, wound up indelibly on the tourist map. That means day-trippers aplenty. Still, we think this town, located smack in the middle of Italy, remains well worth a stop for a day or an afternoon. The views alone are gorgeous, spreading from this dramatic hilltop town over the rolling countryside and Lake Trasimeno. And there are lots of worthwhile sites, like the Museo dell’Accademia Etrusca, chock-full of ancient Etruscan gems from the nearby area.

And towns aside… don’t miss our video of Tuscany’s gorgeous countryside, below!