Though Paulistas do love their cars, most São Paulo neighborhoods can still easily be explored on foot. Just be very careful when crossing the street. São Paulo has the highest number of motorcycle couriers in the country, and motorcycles are responsible for the highest number of pedestrian deaths. Be particularly careful when crossing in between stopped cars; motorcycles often ride at high speed between lanes.
The original city of São Paulo was founded in 1554 on a hilltop between two rivers, the Tamanduatei and the Anhangabaú. The original site is now occupied by a partial reproduction of the old mission called the Pátio do Colégio. Close by, the Cathedral da Sé (also called the Metropolitan Cathedral) was completed only in 1954, though the square it occupies -- the Praça da Sé -- has had a church on it since the city's founding. Throughout the city center, streets veer off from and intersect with each other in odd and intriguing ways.
Key architectural sights in this area include the all-white Banespa Tower and the 1920s Martinelli Building. Two of the key pedestrian streets are Rua Direita and Rua São Bento, which leads northward to the São Bento Monastery. This, too, dates from the 20th century, but the site, high on the banks of what was once the Anhangabaú River, dates back to 1600.
The river itself was long ago filled and turned into a freeway, an act of ecological madness for which the city has paid ever since with flooded roadways. Where the freeway enters downtown (opposite the monastery), it's been sunk beneath a huge civic plaza called the Parque Anhangabaú. At either end, the park is crossed by two high viaducts, the pedestrian-only Santa Ifigênia Viaduct in the north and the Viaduto do Chá in the south.
Going across the middle of the Parque Anhangabaú you come out on the far side in the Praça Ramos de Azevedo, upon which stands the pretty Beaux Arts Teatro Municipal. This bank of the Anhangabaú is often called Nova Centro or New Centro, to distinguish it from the old center, Centro Velho, across the way. The buildings are newer, and apartments and hotels are mixed in with the office towers. From the Teatro Municipal a number of crowded pedestrian streets -- avenidas 7 de Abril, Baron de Itapetininga, and 24 de Maio -- lead west through downtown to the large and green Praça República.
Going northward from here leads through the run-down Luz neighborhood to the high Victorian Luz Station and adjacent Luz Park. Nearby one also finds the Pinocoteca do Estado and the Sacred Art Museum.
Take a Break -- While strolling the historic part of downtown, duck into the Pátio do Colégio. The Café do Páteo (tel. 011/3105-6899; Tues-Sun 9am-5pm), has a lovely garden and terrace where you can rest your legs over a coffee and slice of cake.
Higienópolis (Healthy City) owes its name to a blatant bit of developer marketing. At the beginning of the 20th century wealthier Paulistas were starting to move out of Centro to get away from the mosquito-infested swamps around the banks of the Anhangabaú River. Green and leafy Higienópolis was one of most sought-after destinations. Even today some of the elegant mansions from 80 years ago still remain. It lies on a slight rise west of Centro, centered around Rua Higienópolis and Avenida Angélica. It's here you'll find the small but restaurant-packed Praça Vila Boim and the Museu Arte Brasileira (FAAP), as well as one of the city's nicest malls, the Shopping Pátio Higienópolis.
What is currently called Jardins (gardens) is a combination of a number of neighborhoods such as Jardim Europa, Jardim Paulista, and Jardim America that extend southwest in a regular grid pattern (mostly) from the towers and offices of the Avenida Paulista. Built after the Avenida Paulista developed at the end of the 19th century, these neighborhoods were carefully planned according to the principles of the British Garden City movement, including rules on lot sizes and restrictions on apartment buildings. Some of these regulations have fallen by the wayside, though Jardim Europa is still home to mostly villas and mansions. The Rua Augusta, which runs through the heart of the Jardins, now has many hotels and some of the best restaurants in the city. Where Rua Augusta meets Rua Oscar Freire is now the prime shopping area in São Paulo.
What was once a track along a ridgeline through virgin Atlantic rainforest has come quite a way in just over 100 years. Over one million people and 100,000 cars make their way along the Avenida Paulista on any given business day. Laid out back in 1891, the street was designed as a grand ceremonial boulevard, a place for São Paulo coffee barons and factory owners to build their magnificent villas. One of these grand mansions still remains, the Casa das Rosas near the Brigadeiro Metrô stop. Beginning in the '30s, however, the old mansions gave way to office buildings and then ever-higher commercial skyscrapers. Collectively, they make for an impressive statement of wealth and prestige, though individually the architecture is pretty mediocre. There are two worthwhile attractions near the north end of the Avenida: the Museu Arte São Paulo (MASP) and, just opposite, Siqueira Campos Park, also called by its old name, Trianon Park. For shoppers, the south end of the avenue is anchored by a large upscale mall, the Shopping Pátio Paulista.
Linked by a single large arterial, Avenida Brig. Faria Lima, Pinheiros and Itaim Bibi flank the Jardins to the north and south respectively. Pinheiros lies sandwiched between Jardim Paulista and the nightlife-rich Vila Madalena. Itaim Bibi flanks the southeast side of Ibirapuera park. Both are prime residential neighborhoods, with good hotels and dining options. Itaim Bibi is particularly blessed with restaurants. Avenida Brig. Faria Lima also has the Museu Casa Brasileira, and the upscale Shopping Iguatemi mall.
Tucked away behind Pinheiros, Vila Madalena became popular in the '60s and '70s among University of São Paulo staff and students looking for affordable housing. The neighborhood still has a slightly bohemian feel, and many artists and designers have both homes and galleries here. The Vila is also one of the city's most popular dining spots, and pulses with bars and nightlife most evenings until the wee hours. The neighborhood centers around the Rua Aspicuelta, from Rua Harmonia to Rua Murato Coelho.