Begin at the Edifício Copan,designed by Brazilian architect Oscar Niemeyer. Farther up Avenida Ipiranga is Edifício Itália,once the city's tallest building. Continue north along the avenue and turn right on the pedestrians-only Rua Barão de Itapetininga, with its many shops and street vendors. Follow it to the neobaroque Teatro Municipal,in the Praça Ramos de Azevedo. Head east across the square to the Viaduto do Chá, a monumental overpass above the Vale do Anhangabaú—the heart of São Paulo. At the end of this viaduct, walk left down Rua Líbero Badaró until you reach Avenida São João, then turn right to see the gothic Edifício Martinelli. A bit farther along São João, between Rua 15 de Novembro and Rua João Brícola, is the 36-floor Edifício BANESPA. Continue right on 15 de Novembro and you will reach Praça da Sé, the city's true center and the site of the Catedral da Sé.
Head north out of Praça da Sé and right onto Rua Roberto Simonsen, home of the Solar da Marquesa de Santos,the city's only surviving late-18th-century residence. Nearby is the Pátio do Colégio,which marks the spot where the city was founded, and has a nice café. Walk north along Rua Boa Vista, then right down Ladeira Porto Geral and Rua Basílio Jafet until the corner of Rua da Cantareira, where you can see the fully restored Mercado Municipal. Go back to Rua Boa Vista and follow it right onto Largo de São Bento to the must-see Mosteiro de São Bento.
This route requires two to three hours on foot, depending on where you choose to stop. Start early so you can linger at your leisure. Streets are less crowded on weekends, but some buildings are closed. On Sundays and holidays you can do a carriage tour. Pickpocketing can be a problem, so keep a low profile, don't wear expensive jewelry or watches, and bring only what money you absolutely need. Touring with a guide usually provides some extra security.