The major thoroughfare of Avenida Brigadeiro Faria Lima marks the southwestern frontier of Jardins. South lies the upscale commercial neighborhood of Itaim Bibi, where some of the city’s achingly trendy restaurants and bars open and close with impressive velocity. North are the adjacent bairros of Pinheiros and Vila Madalena. Pinheiros mixes a forest of commercial high-rises with some interesting boutiques, galleries, restaurants, and a lively nightlife scene.

North of Pinheiros, Vila Madalena is Sampa’s bohemian bairro par excellence. Originally, the area was a blue collar neighborhood where workers lived in small bungalows surrounded by gardens where they raised livestock and vegetables. In the 1970s, students and professors from the nearby University of São Paulo—along with artists, musicians, and hippies—began to migrate here for the affordable housing combined with a relaxed, bucolic setting. Many have never left, which explains the lingering intellectual/artist vibe tinged with vestiges of hippiedom and accounts for street names such as Rua da Harmonia (Harmony), Rua da Simpatia (Sympathy), and Rua do Girassol (Sunflower).

By day, Vila Madalena is a wonderfully laid-back place to wander around. Rua Aspiculta and surrounding streets such as Rua Fradique Coutinho and Rua Fidalga are lined with funky boutiques, second-hand stores, and numerous art galleries where you can spend hours browsing. At night, the bairro buzzes with activity as its restaurants, bars, and clubs fill up with a mixed and alternative crowd.