Osteria del Teatro, on a quiet street near Piazza Signorelli, is one of the town's longer-running serious restaurants. The kitchen does the great Tuscan dishes — bistecca alla fiorentina, peposo (slow-cooked beef stew with peppercorns), pici al ragù di cinghiale — with care and good ingredients.
The dining room is in a vaulted 17th-century building. The wine list is heavy on local Cortona DOC reds and other small Tuscan producers. Higher-end prices, but worth it.