Castel del Piano: Palio Town on Amiata’s Western Slope

A working town on the Grosseto side of Monte Amiata with a bareback Palio every 8 September, the road up to the Macinaie, and a place in the Montecucco wine zone.
Castell’Azzara and Selvena: Dice, Cinnabar, and Karst Woods

The highest comune seat in the province of Grosseto, named for a medieval dice game, with the cinnabar-mining village of Selvena and the karst woods of Monte Penna next door.
Roccalbegna: Lorenzetti Panels Beneath Two Fortresses

A small fortified village in the upper Albegna valley, with three panels by Ambrogio Lorenzetti in its parish church and a fire rite every 24 November in the hamlet of Santa Caterina.
Semproniano: Templar Legends and Open Cellars in Southern Amiata

A quiet village on the southern edge of Amiata, with the limestone-perched hamlet of Rocchette di Fazio, an October open-cellar festival, and a project to rescue centuries-old olive trees.
Rocca d’Orcia: The Salimbeni Stronghold Where Saint Catherine Stayed

Rocca d’Orcia Tuscany: the Salimbeni fortress of Tentennano, Saint Catherine’s 1377 stay, and the private castle of Ripa d’Orcia. Plan your visit here.
Castiglione d’Orcia: Two Fortresses and a Madonna’s Swallow

Castiglione d’Orcia Tuscany: two fortresses on one ticket, a Simone Martini Madonna, and the valley’s oil cooperative. Plan your visit here.
San Quirico d’Orcia: An Emperor, a Pisano Portal, and a Garden

San Quirico d’Orcia Tuscany: Barbarossa’s 1155 visit, a Giovanni Pisano portal, and a Medici-era garden. Read our guide and plan your stop.
Bagno Vignoni: A Square of Hot Water Nobody Swims In

Bagno Vignoni Tuscany: a square built around a hot pool, mills that ground all summer, and the rules on bathing. Read before you visit.
Radicofani: The Pope’s Border Fortress, Blown Up on Purpose

Radicofani Tuscany: a papal fortress on a volcanic rock, a Medici posthouse, and Dante’s bandit. Plan your visit to the Val d’Orcia’s southern gate.
Bagni San Filippo: A Free Hot Stream and Its Rules

Bagni San Filippo Tuscany: a free hot stream, white limestone, and years of rows over access. Read the rules before you go and plan your visit.