While wine production has been a part of Montalcino life for centuries, it took the 1888 creation of Brunello di Montalcino—a gorgeous twist on Chianti blends made with 100 percent Sangiovese grapes—to put the medieval town’s name on everyone’s lips. Wine fans will delight in visiting area vineyards and producers, many still small and family-owned, and sampling vintages both at the source and in local bars. If you’re not a drinker, never fear: There’s plenty else in the fairy-tale town that will charm you, including the Piazza del Popolo main square, with its Gothic loggia; the 14th-century Rocca fortress, boasting breathtakingly vast views from its ramparts (a hotspot during sunset); and the Museo del Vetro, a glass museum set inside a former castle that showcases delicate works by the ancient Egyptians on down to modern-day Venetians. Stroll the maze-like cobblestone streets, popping into the small shops and cafés, to get a feel for the place. Better yet, visit during a festival; among the annual celebrations are Montalcino Honey Week in September and the Jazz & Wine Festival each July.

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Home of the Red

While wine production has been a part of Montalcino life for centuries, it took the 1888 creation of Brunello di Montalcino—a gorgeous twist on Chianti blends made with 100 percent Sangiovese grapes—to put the medieval town’s name on everyone’s lips. Wine fans will delight in visiting area vineyards and producers, many still small and family-owned, and sampling vintages both at the source and in local bars. If you’re not a drinker, never fear: There’s plenty else in the fairy-tale town that will charm you, including the Piazza del Popolo main square, with its Gothic loggia; the 14th-century Rocca fortress, boasting breathtakingly vast views from its ramparts (a hotspot during sunset); and the Museo del Vetro, a glass museum set inside a former castle that showcases delicate works by the ancient Egyptians on down to modern-day Venetians. Stroll the maze-like cobblestone streets, popping into the small shops and cafés, to get a feel for the place. Better yet, visit during a festival; among the annual celebrations are Montalcino Honey Week in September and the Jazz & Wine Festival each July.

Rolling Hills of Tuscany's Chianti Region

Driving through Tuscany this May, my husband and I loved everything about the region, from its classic Tuscan architecture and warm colors to its rich food and delicious wine. And we found no better place to enjoy Tuscany’s wine than the world-famous Chianti Region. Lying in Tuscany between Siena and Florence, the Chianti Region is best known for its “Chianti Classico” wine. But not only is the region’s wine delicious, its landscape is absolutely beautiful as well. These lush rolling hills, lying just outside Montalcino, are typical of the Chinati Region and combined with the quaint Tuscan towns and beautiful architecture of the region to make our time in Chianti unforgettable.

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