Montalcino (Tuscany)

Set on a hillside in the Val d’Orcia, a part of Tuscany offering some of the region’s most phenomenal landscapes, Montalcino, like its larger counterpart Montepulciano, is a major wine town. Here the star attraction is Brunello di Montalcino, one of Italy’s costliest wines (prices typically range from about $55 to close to $1500), made entirely from Sangiovese grapes. While archival records show a Brunello produced in the Middle Ages, the local Biondi Santi family pioneered the development of the type of wine that’s made today. You can visit their iconic winery, the Tenuta Greppo, a short drive (3 kilometers) from Montalcino for a private tour and tasting  (book in advance). In the town of Montalcino itself, wander the medieval streets, and climb the ramparts of the 14th-century castle to take in the astounding panorama of the surrounding countryside. Then visit the enoteca (La Fortezza) in the fortress to sample some of those renowned Brunellos.

Montefalco (Umbria)

Although likely to have been first settled in pre-Roman times, Montefalco’s visual identity comes from the Middle Ages. Today it enjoys international commercial renown from the production of Sagrantino, the powerful red wine made from the indigenous grape of the same name that grows in a select area in the hilly vineyards around the town. There are many superb wineries to visit nearby like Arnaldo Caprai, now run by the founder’s son, Marco Caprai, a key figure in the evolution of modern-day Sagrantino; and Scacciadiavoli, one of the oldest wineries in the area. (You’ll find a number of wine bars in Montefalco where you can also sample the hearty wine.) Before your tastings take time to stroll the town’s cobblestone streets, flanked by flower bedecked (in warm weather) stone houses, observing the centuries-spanning architecture. Stop by the St. Francis Church Museum where you can see beautiful frescoes by the influential Renaissance painters Benozzo Gozzoli and Perugino, who was Raphael’s teacher.

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