Tuscan Chianti & Pecorino Trail: Vineyards, Medieval Hilltowns & Val d'Orcia Panoramas

Piazza Giacomo Matteotti, 50013 Campi Bisenzio FI, Italy

💡 Walk beneath the vaulted loggias and stop at the historic Antica Macelleria Falorni to sample wild boar finocchiona before the mid-morning crowds arrive

Località Castello di Montefioralle, 22, 50022 Montefioralle FI, Italy

💡 Park outside the northern stone gate; this tiny, quiet medieval walled village offers pristine circular cobblestone alleys without tourist shops.

50028 Badia a Passignano, Metropolitan City of Florence, Italy

💡 Admire the fortified 11th-century Vallombrosan abbey framed by cypress trees, surrounded by the historic vineyards of the Antinori estate.

Via Lamole, 6, 50022 Greve in Chianti FI, Italy

💡 Sit down for lunch on the panoramic terrace perched 600 metres up; order the handmade pici with duck ragù paired with a local Chianti Classico.

Località Il Becco, 101/a, 53017 Radda in Chianti SI, Italy

💡 Take a guided tour of the gravity-fed underground barrel cellars built right into the stony hillsides of Radda in Chianti.

Viale di Circonvallazione, 25, 53026 Pienza SI, Italy

Via S. Carlo, 2/4, 53026 Pienza SI, Italy

💡 Taste a flight of regional Pecorino di Pienza, ranging from semi-aged to rounds matured under walnut leaves or sealed in ash.

Podere Vitaleta, 53027 San Quirico d'Orcia SI, Italy

💡 Park at the roadside car park and enjoy the gentle 10-minute walk through the wheat fields to reach this iconic stone chapel.

Via Dante Alighieri, 42, 53027 San Quirico d'Orcia SI, Italy

💡 Dine in the shaded garden courtyard under the wisteria pergola for lunch; order the sliced beef tagliata finished with Tuscan rosemary extra virgin olive oil.

Scheduled Downtime

53027 Bagno Vignoni, Province of Siena, Italy

💡 Conclude the route at sunset by wandering through the ancient cliffside water channels and olive terraces overlooking the valley, right beside Bagno Vignoni's ancient central thermal pool.