In the heart of Anghiari
The first thing you'll notice as you approach Anghiari is the long straight road called Ruga di San Martino: an 8 km arrow-straight stretch of asphalt. But once inside the town’s mighty walls, Anghiari will win you over with its alleys, Piazza del Mercatale and the tobacco fields of Kentucky leaves used to make Tuscan cigars. Pop into the Battle and Anghiari Museum and Palazzo Taglieschi to spot wood sculptures like Jacopo della Quercia’s Madonna and Child, 16th–17th century paintings, ancient weapons, and a 1530 organ. Feeling adventurous? Head out on the trails of Monti Rognosi Park and the Sovara Valley.
Borgo di Anghiari
Sansepolcro, like a painting by Piero della Francesca
The main town of the Valtiberina, Sansepolcro is closely tied to the work of Piero della Francesca. As you wander its streets, lined with noble palaces and churches and protected by the Medici fortress, you’ll feel like you’ve stepped inside one of his paintings—and you might even recognise some scenes! Don’t miss the Civic Museum with its Renaissance masterpieces, including the 15-year project Madonna della Misericordia, the iconic Resurrection with Piero’s self-portrait (second soldier from the left), and more. A minute away stands the Cathedral of San Giovanni Evangelista, where the Carolingian Volto Santo crucifix gives off a calm, powerful vibe.
Make time for the Aboca Museum, a hands-on journey into herbal history. From the Aboca Experience section to botanical plates, the room of herbs, the ancient pharmacy and even a poison chamber—kids and grownups will love it. Hungry after your visit? Grab a bite at Ristorante Fiorentino, serving local fare since 1807.
In San Quirico d’Orcia, surrounded by wonder
When the green outside your car window gets brighter, you’ve reached the Val d’Orcia—a land of cypress trees, villas, and UNESCO heritage status since 2004. Here, nature and humans live in perfect harmony. Before diving into the hills, stop at San Quirico d’Orcia and stroll through the Horti Leonini, a pretty Italian garden created in 1585 by Diomede Leoni, a friend of Michelangelo. Wander around and you'll come across the impressive Collegiata of Saints Quirico and Judith and the thousand-year-old Church of Santa Maria Assunta on the ancient Via Francigena. For a unique snack, check out Vald’O—a wine bar filled with books, art and local crafts.
Collegiata dei Santi
Bagno Vignoni’s water square
One of the area’s most magical places, Bagno Vignoni sits just minutes from San Quirico d’Orcia. A unique village known for its thermal springs since Etruscan times, its main square is actually a huge water basin (49 x 29 m) reflecting the Church of San Giovanni Battista and the 16th-century loggia of Santa Caterina. Stroll downhill where the spring water joins the Orcia river to explore the Mills Natural Park: four medieval mills carved into the rock, the old Roman thermal pool (free access!) and Languorino, a laid-back spot for platters, pasta and grilled meat.
Bagno Vignoni
Not just wine in Montepulciano
With its picture-perfect square best enjoyed with a glass of Nobile wine, Montepulciano sits proudly between Valdichiana Senese and Val d’Orcia. Famous for its DOCG wine made from ‘prugnolo gentile’ Sangiovese grapes, this town has plenty more to offer. Start from Porta al Prato and wander Corso: you’ll find wine cellars, stunning buildings, Michelozzo Square, the Clock Tower, the Town Hall and the Cathedral of Santa Maria Assunta. Tired of climbing the hilly streets? Look below your feet: seven ancient underground wine cellars stretch below the town, ageing wine for centuries. Want to taste? Head to Cantina de Ricci (looks like a cathedral!), Cantina Poliziano (family-run gem), or Avignonesi for biodynamic wine fans.
Montepulciano
