5 Picture-Perfect Villages to Explore in Tuscany, Northern Italy
Tuscany, in northern Italy, is a region celebrated for its rolling hills, vineyards, and picturesque villages—each offering its own unique slice of Italian heritage. Here are five charming destinations you won’t want to miss on your journey through the Tuscan countryside.
Greve in Chianti: A Rustic Gem in Wine Country
Chianti is world-renowned for its exceptional wines, but the area’s villages are just as delightful. Greve in Chianti stands out with its triangular town square, graceful arches, and inviting cafés. Just above the town lies Montefiorale, a fortified hamlet filled with historic stone houses and winding alleys—perfect for a scenic stroll.
Planning a trip to Tuscany? You might enjoy these too:
- Visit the birthplace of Leonardo da Vinci, where some of his original works are on display.
- Discover Tuscany’s lesser-known islands for a unique coastal escape.
- Explore a mountaintop medieval village that feels like a journey through time.
San Gimignano: Towers of the Past
Often called the "medieval Manhattan" of Tuscany, San Gimignano is famed for its cluster of ancient towers, a symbol of historic rivalry among noble families. Recognized by UNESCO for its cultural value, the town features highlights such as the elegant Piazza della Cisterna and the richly decorated Duomo. Contemporary art lovers will appreciate the acclaimed Galeria Continua.
Montalcino: The Home of Brunello
Nestled near the stunning Val d’Orcia, Montalcino is synonymous with Brunello, one of Italy’s finest red wines. This hilltop town is enclosed by robust medieval walls and crowned by a formidable 14th-century fortress. The central Piazza del Popolo maintains its Renaissance charm, and a visit to La Fiaschetteria—an old-world café open since 1888—is a must for those seeking an authentic aperitivo experience.
Pitigliano: Carved Into the Cliffs
Located in the heart of Maremma, Pitigliano sits dramatically atop a cliff of volcanic tuff. Its sloping alleys and cozy squares offer a magical atmosphere, especially around the Renaissance-era Palazzo Orsini. The town also holds cultural significance in the district known as Little Jerusalem, where a historic synagogue and remnants of a once-thriving Jewish community still remain.
Giglio Castello: Tuscany’s Island Fortress
Tuscany’s beauty extends beyond the mainland to its idyllic islands. On Giglio Island, overlooking the Tyrrhenian Sea, sits Giglio Castello—a hilltop village still encircled by its original medieval walls. A commanding fortress towers over the settlement, which once defended the island from pirate attacks. This peaceful retreat offers dramatic views and a taste of island life with a historical twist.