Driving in the city isn't recommended because of the heavy traffic (nothing moves at rush hour, especially when it rains), daredevil drivers, and inadequate parking. If you do opt to drive, there are a few things to keep in mind:
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. You can take avenidas Paulista, Brasil, and Faria Lima southwest to the Morumbi, Brooklin, Itaim, and Santo Amaro neighborhoods, respectively. 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. Booklets of 10 tickets cost R$20. 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$3 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.
Avis (Rua da Consolação 335, Centro. 011/3259-6868 or 0800/19-8456). Hertz (Rua da Consolação 439, Centro. 011/3258-9384 or 4336-7300). Localiza (Rua da Consolação 419, Centro. 011/3231-3055 or 0800/99-2000).