The City Theater (412-431-2489) has been putting on live productions since the '70s and frequently commissions new plays by local and national artists. The theater is on the South Side, just off Carson Street's long stretch of bars and restaurants.
At Kenny B's (412-201-1626), just down the street from the Renaissance Pittsburgh Hotel, you can eat a classic diner breakfast anytime while sitting in little red-and-black swivel chairs. Come back at lunch or dinner for the Cuban dishes or the Cheeseburger in Paradise. If you're lucky, the owner will tell you his stories about meeting Jimmy Buffett.
Ali Baba (412-682-2829) has won awards from nearly every publication in Pittsburgh for its large menu of inexpensive, tasty dishes. It's just a block from the Carnegie Museum of Art.
Bossa Nova (412-232-3030) in the Cultural District serves Spanish-style tapas appetizer-sized dishes that add up to dinner with occasional Asian accents.
At Station Square, a sort of horizontal Tower City on the South Side, try one of the restaurants in the old train station itself: the Grand Concourse
(412-261-1717), where you can dine on seafood in the gorgeous baroque lobby of the old Pittsburgh and Lake Erie Railroad, or the Gandy Dancer bar (same number).
The Renaissance Pittsburgh Hotel (412-562-1200), a historic building in the Cultural District, is close to several restaurants and theaters and a short walk across a bridge from the Warhol Museum. Built in 1906 and renovated in 2001, its two-story marble lobby is dazzling, and the hollow, arched space in the side of the building gives many rooms a view of the Allegheny River.