7 Wonderful Hilltop Towns in Tuscany ...

1. San Gimignano

Among the most famous of the hilltop towns in Tuscany is San Gimignano, about 63 km south-west of Florence. The well-preserved medieval architecture of its historic centre has made this gorgeous town a UNESCO World Heritage Site. Lovely churches like the Collegiata and the Sant’Agostino house fine medieval and Renaissance works of art and the piazzas are great places to relax. Three walls, dating from as far back as the 12th and 13th centuries, encircle the main town and the views from here over the vineyards where the grapes for white wine are grown are breathtaking. From the surrounding countryside, you’ll be able to see why San Gimignano is also known as the Town of Fine Towers: Fourteen of its ancient towers have been preserved, making it unique among most of the region’s towns and cities.

2. Cortona

Legend has it that 108 years after the Flood, Noah came to the Valdichiana and loved it so much that he stayed for 30 years. A little more than 150 years later, one of his sons built the hilltop village of Cortona. It’s easy to see why they would have preferred this site: The views over the valley and Lake Trasimeno, where Hannibal ambushed the Roman army, are simply stunning. You may recognize the town from literature and the big screen too, since this is where Frances Mayes’ Under the Tuscan Sun was set. Some scenes from Life Is Beautiful were shot in these steep, narrow streets too. You can learn more about Cortona’s Etruscan past by visiting the Museo dell’Accademia Etrusca and the Etruscan tombs in the area. If religious art is more your thing, don’t miss the Diocesan museum, where one of the treasured paintings is Fra Angelico’s Annunciation. Located a little over 120 km south-east of Florence, a visit to Cortona will remind you that life is, indeed, beautiful.

3. Siena

A little less than 90 km south of Florence, Siena is one of the most visited Tuscan hilltop towns. Another UNESCO World Heritage Site, the town was founded by the Romans: according to legend, by Senius, the son of Remus, one of the twin brothers famously raised by a wolf. Siena is positively bursting with architectural treasures, among them the 12th-century cathedral. The town also has a rich artistic heritage and it was here that the reddish brown pigment known as sienna was first produced during the Renaissance. July sees some great music festivals here but if you’re in Siena on either 2 July or 16 August, don’t miss the Palio, an adrenalin-inducing medieval horse race.

4. Pienza

If Milton Keynes had been built a few centuries earlier and about 120 km south-east of Florence, it might have looked like Pienza. Unlike many hilltop towns in Tuscany, Pienza doesn’t date from medieval times or before. In the 14th century, Pope Pius II had the entire village where he had been born rebuilt into what he regarded as the ideal humanist town. It set the trend for Renaissance urban planning and today the town centre is a UNESCO World Heritage Site. Buildings like the Cathedral and the different palazzi are perfect examples of early Renaissance architecture and some house priceless aroks of art from the era. For example, in the Palazzo Vescovile you’ll find Pietro Lorenzetti’s stunning Madonna with Child. For breathtaking views of the Val d’Orcia and Mount Amiata, head to the perfectly manicured Italian Renaissance garden at the Palazzo Piccolomini. While you’re in town, be sure to try that other thing it’s famous for: pecorino cheese. On the first Sunday in September, you may even want to test your aim at a cheese-rolling competition known as Cacio al Fuso, or ‘cheese to the spindle.’

5. Montepulciano

A little to the east of Pienza lies Montepulciano. Like so many Tuscan hilltop towns, it features beautiful architecture dating from the Middle Ages and the Renaissance, as well as gorgeous views. The real reason to come here though is the opportunity it offers to taste la dolce vita. Pork, lentils, cheese, honey and a pici, a type of pasta that resembles very thick spaghetti, are some of the culinary delights from the area. The vineyards around town produce a red wine known as Vino Nobile, considered as one of the finest to come from Italy. It’s probably no wonder that one of the most famous annual events here involves wine barrels. The Bravio delle Botti takes place on the last Sunday in August and many of the townspeople don medieval dress for the event. Competitors push huge wooden barrels up the steep and narrow streets to try and win a colorful cloth banner known as the ‘bravio.’

6. Montecatini Terme

If simply exploring and admitting the views from a hilltop town in the Tuscan region isn’t relaxing enough for you, be sure to visit Montecatini Terme, about 50 km west of Florence. The old part of town on top of the hill features lovely medieval architecture and can be visited by taking the cable car up. However, Montecatini Terme is famous for its spas, the first of which were constructed in 1530 at the foot of the hill. Laze around in the thermal waters or indulge in spa treatments and imagine the celebrities of years gone by, people like Giuseppe Verdi, who visited too. In summer, the town hosts a renowned opera festival.

7. Volterra

If you’re a Twilight fan, you probably know that the place to go if you want to avoid being bitten by a vampire is Volterra. This is where the powerful Volturi live. What you maybe didn’t know was that Volterra really exists. It’s about 85 km south-west of Florence and dates back at least 10,000 years. While much of the architecture is medieval, you’ll also find a Roman amphitheatre and Etruscan tombs and walls. The Guarnacci Etruscan Museum is fascinating but if you want a very different experience, have a meal at Fortezza Medicea that overlooks the town. This ancient fortress is now a maximum security prison but also houses an unusual restaurant: one where all the staff members are actually inmates. You’ll have to book far in advance, though, because as many people have already discovered, prison food has never tasted this good.

Aren’t the hilltop towns in Tuscany magnificent? There are also countless villages hidden in hilly nooks and crannies. Tuscany is truly one of the best regions in Europe for travelers. Have you been?