Day 1: Get Acquainted with São Paulo
Get to know one of the world’s largest cities by heading directly into its heart with a tour of neo-Gothic Sé Cathedral and a few hours of free culture at the Centro Cultural Banco do Brasil. When you get hungry, visit the bustling Mercado Municipal for a giant, world-famous mortadella sandwich, followed by an afternoon of art at the gloriously restored Pinacoteca do Estado, or immerse yourself in the beautiful sounds of Brazil’s mother tongue at the Museu da Língua Portuguesa.
Architecture aficionados and urban aesthetes can get their fill atop the Art Deco-inspired Banespa tower, with 360-degree panoramas of the megalopolis in the daytime, or spectacular nighttime views from the 41st-floor restaurant and bar in the EdifícioItália. Wrap up the first night with al fresco dining and a stroll along Avenida Paulista or in one of the many funky nightspots along Rua Augusta.
Day 2: Explore the City's Parks
Start the day up on Avenida Paulista, where you can choose between indoor art action at the São Paulo Museum of Art (MASP) or explore the small patch of tropical forest just across the street, Trianon Park.
Smack in the middle of town, São Paulo’s vast Ibirapuera Park offers visitors hiking and biking trails to keep body together along with a clutch of artfully-designed museums to take care of the mind. The absorbing Museu Afro Brasil and the engaging Museum of Modern Art (MAM) are two of the park’s must-sees. Afterwards, take a cab over to Vila Madalena and explore the graffitied alleyways of the Beco do Batman (Batman’s Cave) and on weekends, enjoy the sights and sounds of the popular flea markets at Praça Benedito Calixto in Pinheiros or in Liberdade, São Paulo’s Japantown. You can end the night with samba at one of the boisterous botecos (gastropubs) in Vila Madalena or go full-on kitsch with karaoke in Liberdade.
Day 3: Take a Day Trip
If you start to come down with city-fatigue, skip town to either the Litoral Paulista—the breathtaking stretch of Atlantic coastal beaches, including Guarujá and Ilhabela, only a couple hours’ drive southeast—or to Embu das Artes, a bohemian artist enclave just a few miles to the west.