Osteria del Teatro
On Via Maffei, just off the main corso, Osteria del Teatro has been feeding Cortona's most discerning locals and well-travelled visitors since 1992. Chef-owner Emiliano Rossi sources ingredients obsessively — the black truffles come from the surrounding hills, the Chianina beef is raised in the valley below, and the pasta is made fresh each morning.
What to Order
Start with the pici al tartufo nero — thick hand-rolled spaghetti tossed with fresh black truffle shaved tableside. It is one of the finest pasta dishes in the region, and the portion is generous enough to make you reconsider ordering a secondo. Resist: the bistecca di Chianina, grilled over charcoal and served simply with Cortona extra-virgin olive oil and sea salt, is unmissable.
The wine list leans heavily on local Cortona DOC Syrah and Sangiovese, plus a well-chosen selection from Montepulciano and Montalcino. Ask sommelier Marco for a glass of Tenimenti Luigi d'Alessandro Cortona Syrah — it pairs perfectly with the truffle pasta and costs less than you'd expect.
The Room and the Booking
The dining room occupies a vaulted stone cellar with exposed brick arches, terracotta floors and candlelight that makes everyone look like a Signorelli portrait. In summer, a handful of tables spill onto the narrow street outside — reserve one of these for the full Cortona evening experience.
Reservations are essential, particularly in July and August when the town fills for the Cortona on the Move photography festival. Book at least a week ahead online or by phone; the staff speak excellent English.
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