Vicchio: The Small Town That Made Two of the Greatest Painters in History
Vicchio gave the world Giotto and Fra Angelico — two painters who changed Western art. It also hid a radical priest, a rebel school, and Tuscany’s newest wine region.
Aulla: The Town That Was Erased and Built Again
Aulla was almost completely destroyed in WWII and rebuilt from scratch. What survived — a 9th-century abbey and a Renaissance fortress — tells the story of everything that didn’t.
Castiglion Fiorentino: The Loggia That Isn’t Vasari’s
Castiglion Fiorentino has a valley-framing loggia, Etruscan ruins, Benigni’s birthplace, and a June horse palio — all without Cortona’s crowds.
Bagnone: The Borgo That Sounds Like Water
Bagnone cascades down a hillside above a rushing torrent, crowned by a Malaspina castle and crossed by a medieval bridge. It earned its Orange Flag for a reason.
Cetona: From Neanderthals to Valentino
Cetona sits beneath Monte Cetona, where Neanderthals lived 50,000 years ago. The medieval borgo above is one of Tuscany’s most perfectly preserved.
Equi Terme: Caves, Hot Springs, and a Canyon Between Two Mountain Ranges
Equi Terme packs Neanderthal-era caves, 27°C thermal springs, a zipline, and the 50-meter canyon walls of the Stretti di Giaredo into one tiny Lunigiana hamlet.
Chiusi: Where an Etruscan King Built a Labyrinth (Maybe)
Chiusi was one of the most powerful Etruscan cities — now it has an underground labyrinth, painted tombs, early Christian catacombs, and lake-grilled fish.
Filattiera: The Byzantine Garrison on the Pilgrim Road
Filattiera began as a Byzantine fortress called Kastron Soreon in 610 AD. Its Romanesque church of river pebbles is one of the most elegant stops on the Via Francigena.
Cortona: What “Under the Tuscan Sun” Didn’t Tell You
Beyond the bestseller, Cortona holds the third-longest Etruscan inscription, a Futurist mosaic pilgrimage, sphinx-guarded tombs, and Italy’s largest steak grill.
Bibbiena: The Practical Heart of Tuscany’s Most Forested Valley
Bibbiena is the Casentino’s largest town — a working hub with Renaissance palaces, a Donatello-school Madonna, and the Sagra delle Sagre that gathers the entire valley’s food traditions.