Torrita di Siena and Montefollonico: Donkeys, Vin Santo and a Hilltop Secret
Torrita di Siena runs a donkey palio with eight contrade. Above it, the tiny village of Montefollonico judges homemade Vin Santo from 78 producers.
Foiano della Chiana: 487 Years of Giant Puppets and Garlic
Foiano della Chiana hosts Italy’s oldest documented Carnival since 1539, and hides one of Tuscany’s greatest concentrations of Della Robbia terracottas.
Lucignano: Four Rings, One Golden Tree
Lucignano’s four concentric ring streets spiral to a piazza hiding the world’s only tree-shaped reliquary. A Valdichiana village unlike any other.
Monte San Savino: The Sculptor’s Town That Lost Its Synagogue
Monte San Savino gave Italy the sculptor Sansovino, Pope Julius III, and the Arezzo region’s most important Jewish quarter — destroyed in a 1799 pogrom.
Montepulciano: First DOCG, First Pievi, and One Very Steep Barrel Race
Montepulciano produced Italy’s first DOCG wine and now its most precise subzone system. Add underground cellars, a barrel race, and Tuscany’s finest piazza.
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.
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.
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.
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.
Meet Stefano Amerighi: The Biodynamic Farmer Behind Cortona Syrah
Stefano Amerighi Cortona Syrah: meet the biodynamic farmer behind Tuscany’s Syrah revival. Read his story and learn how to arrange a visit.