The principal highways leading into São Paulo are: the Dutra, from the northeast (and Rio); Anhangüera and Bandeirantes, from the north; Washington Luis, from the northwest; Raposo Tavares, from the west; Régis Bittencourt, from the south; and Anchieta-Imigrantes, from Santos in the southeast. Driving in the city isn't recommended, however, because of the heavy traffic (nothing moves at rush hour, especially when it rains), daredevil drivers, and inadequate parking. You'll also need to obtain a temporary driver's license from Detran, the State Transit Department, which can be a time-consuming endeavor.
The high-speed beltways along the Rio Pinheiros and Rio Tietê rivers—called Marginal Tietê and Marginal Pinheiros—sandwich the main part of São Paulo. Avenida 23 de Maio runs south from Centro and beneath the Parque do Ibirapuera via the Ayrton Senna Tunnel. Avenida Paulista splits Bela Vista and Jardins with Higienópolis and Vila Mariana as bookends.
You can cut through Itaim en route to Brooklin and Santo Amaro by taking avenidas Brasil and Faria Lima southwest to Avenida Santo Amaro. Avenida João Dias and Viaduto José Bonifácio C. Nogueira cut across the Pinheiros River to Morumbi. The Elevado Costa e Silva, also called Minhocão, is an elevated road that connects Centro with Avenida Francisco Matarazzo in the west.
In most commercial neighborhoods you must buy hourly tickets (called Cartão Zona Azul) to park on the street during business hours. Buy them at newsstands, not from people on the street, who may overcharge or sell counterfeited copies. Booklets of 10 tickets cost R$28. Fill out each ticket—you'll need one for every hour you plan to park—with the car's license plate and the time you initially parked. Leave the tickets in the car's window so they're visible to officials from outside. After business hours or at any time near major sights, people may offer to watch your car. If you don't pay these "caretakers," there's a chance they'll damage your car (R$2 is enough to keep your car's paint job intact). But to truly ensure your car's safety, park in a guarded lot, where rates are R$5–R$7 for the first hour and R$1–R$2 each hour thereafter.
Invest in the Guia São Paulo Ruas, published by Quatro Rodas, which shows every street in the city. It's sold at newsstands and bookstores for about R$30.