Home to the artists and intellectuals of Sao Paulo (and those who forever pose as such), Vila Madalena has a nightlife and dining scene with an atmosphere to match. Located in the western part of the city in the Pinheiros district, there are a ton of graffiti-strewn streets and alleys, as well as a deluge of great little bars that have an alternative flair, particularly on Rua Delfina and Rua Aspicuelta. You won't find any super-clubs here, a blessing for many, but hip hang-outs abound. Bar Pirajá, Genésio, Salve Jorge, and Empanadas Bar all have excellent local reputations.
For a great selection of eateries beyond the snacks that you can grab at any of bars or cafes in Vila Madalena, try taking a walk down the short, centrally-running Rua Wisard and branching off on any of its side streets. There are plenty of quality South American restaurants in the vicinity.