The Breathtaking Hilltop Fairytale Town In Italy Is World Famous For Its Unmatched Wine Scene

Italy is famous for its wine, and although there are multiple magnificent wine regions within its borders, its most renowned — and oldest — is Tuscany (or Toscana, in Italian). Scattered through the countryside are family-run vineyards and centuries-old wineries, along with the many enchanting hilltop towns that characterize this area of the country. From the towers of San Gimignano to the Roman ruins in Volterra, there's plenty of classic Italian charm to be found. 

One of the best spots to immerse yourself in the wonders of Tuscany is the fairytale spot of Montalcino. Montalcino is particularly famous for its red wine, including the world-renowned Brunello di Montalcino, one of Italy's most exclusive wines and one of the first to gain the coveted DOCG status — the highest classification of Italian wine quality. In addition to the wine culture, Montalcino is also quintessential Tuscany: Set in the picturesque Val d'Orcia and home to some of Tuscany's most famous landscapes, it's surrounded by fortified walls and has a medieval center that's hardly changed since the 16th century. 

With its strategic location near Siena, Montalcino is an ideal base to explore greater Tuscany. Start in the town itself, at the ancient fortress, La Fortezza. Walk along the ramparts or climb the battlements for incredible views of the surrounding landscape. Then, visit the lovely clock tower in the Piazza del Popolo, the town's main square. Explore the winding alleys, stopping for wine in little shops as you go, or visit one of the churches, such as the large Duomo di Montalcino. 

Outside of town, traverse through the rolling hills and olive groves to see the 12th-century Sant'Antimo Abbey, which, according to legend, was first founded by Charlemagne in 781. Farther afield, swim in the hot springs in Terme di Petriolo or Bagno Vignoni. In addition to Siena, there are plenty of charming hilltop towns not far from Montalcino, such as Pienza, a UNESCO-listed town known for its cheese, and Montepulciano, another ideal base for exploring Tuscany. Take the seasonal vintage train through the Val d'Orcia, or go deep into the Tuscan countryside to see the memorable ruins of the San Galgano Abbey.

Montalcino has earned its spot as one of the best places to visit in Tuscany thanks to its medieval charm but also, of course, due to its wine. Montalcino was known for its wine as far back as the 15th century, although its most famous blend was created in the 19th century. Sample wines fresh out of the cask at some of Montalcino's incredible wineries, such as Biondi Santi, home to the famous Brunello, or at Castello Banfi, one of the most spectacular vineyards in the area. Try eco-friendly wines at Casa Raia, or visit L'Enoteca in the fortress for an array of prized local wines.

Montalcino has the food scene to pair with its excellent wines. At town restaurants or nearby wineries, try specialties made with local products such as asparagus, truffles, wild boar, and olive oil. Montalcino is also known for its honey — beekeepers from all over Italy keep their hives here. Other dishes to sample include ribollita soup, pinci spaghetti, and strozzapreti pasta with Brunello sauce.