There's been a Benedictine monastery on this site by the edge of the Anhangabaú Valley since 1600, just a few decades after São Paulo was founded. The current Basilica de São Bento dates to 1910 and is worth a look if you're passing by, though to tell the truth, despite all the marble, wood, and stained glass that went into the construction, the net effect is far from beautiful. Visitors may be most impressed by the German organ with 6,000 pipes. Come for High Mass on Sunday at 10am, and the service is accompanied by Gregorian chants. Open Saturday to Thursday 6am to noon and 2 to 6pm, and Friday from 2 to 6pm. Gregorian chanting is Monday and Saturday at 7am, and Sunday at 10am.
São Paulo's Metropolitan Cathedral is a curious structure, a blend of Byzantine and High German Gothic. Construction began in 1911, but wasn't completed until 1954. Its best feature may be the Praça da Sé out front, which is lined with stately imperial palms and occupied during the daylight hours by street preachers, some of them quite good. It's open daily 7am to 7pm.
On the other side of Centro on the Largo do Paisssandu stands the pretty yellow Irmandade de N.S. dodo Rosario dos Homens Prêtos. Built by São Paulo's freed-slave community, the church is now something of a refuge for the down and out. Homeless congregate on the steps, and inside the cream-and-ocher interior the offering and donation boxes are housed in thick steel safes.