Duration: ~11 hours 
Season: All year round

From: starting from € 180 per guest

Up to 6 guests

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Cortona: the balcony over the Val di Chiana

Perched on a hill that seems handpicked for perfect photos, Cortona is the kind of town that makes you say "ah, this is why people move to Tuscany after watching a movie." And indeed: this is where "Under the Tuscan Sun" was filmed, and ever since, half the world has dreamed of buying a stone house with an endless view. Steep alleyways, cats napping in the sun, and a view that stretches from the main square all the way to Lake Trasimeno. Tip: walk up (or nearly up) via the Santa Margherita staircase, and wear comfortable shoes — Cortona doesn't go easy on your calves.

Montepulciano: the wine is waiting for you in the cellar (literally)

Montepulciano figured out one fundamental thing: if your town sits on a ridiculously steep hill, you might as well dig tunnels and cellars under every building and fill them with Vino Nobile. Walking down the main street, you're literally strolling above bottles aging in silence beneath the feet of unsuspecting tourists. The Palazzo Comunale at the top has a tower you can climb for an incredible panorama (and to morally justify your third glass of red). Fun fact: the name confuses everyone who assumes Pienza's pecorino cheese is "from Montepulciano" — they're two different towns, but the gastronomic rivalry between them is real and delightfully heated.

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Pienza: the town designed on a drafting table (with pecorino on top)

Pienza is the perfect anomaly: an entire historic center designed in the mid-1400s by a pope (Pius II) who wanted to turn his birthplace into an ideal Renaissance "utopia city." The result: harmonious proportions, squares that look drawn with a ruler, and a nativity-scene atmosphere that makes it a favorite backdrop for Instagram photos. But the real star here is the pecorino: shops along the main street display wheels of Pienza pecorino aged every way imaginable — wrapped in walnut leaves, coated in ash, buried in hay. Fun fact: the lookout point at the back of town offers one of the most photographed views in the whole Val d'Orcia, with rolling postcard-perfect hills that almost look fake.