Continuing along Rua Boa Vista from the Pátio do Colégio brings you to Largo de São Bento. Amid a cluster of high-rise financial buildings is the Mosteiro de São Bento (Largo de São Bento, Centro, tel. 11/3328-8799, www.mosteiro.org.br, 6 a.m.–6:30 p.m. Mon.–Fri., 6 a.m.–noon and 4–6 p.m. Sat.–Sun., free).

Though it dates back over 400 years, the Benedictine monastery has received numerous facelifts over the centuries. Its basilica was built in 1912. Compared with the sober facade, the interior is more ornate. An interestingly subversive pagan touch is the painting of a red sun (representing God) with beams radiating the 12 signs of the zodiac.

Most of the Mosteiro de São Bento is off-limits to visitors since its quarters are home to the Benedictine monks, who not only sing divinely (Gregorian chants are performed at 7 a.m. Mon.–Fri., 6 a.m. Sat., 10 a.m. Sun.), but also bake well: Try the pão de mandioquinha (a type of sweet potato bread) and the bolo Santa Ecolástica, a cake made with apples and walnuts, which are sold on the premises.

Near the Mosteiro de São Bento is a trio of more modern, but equally striking landmarks. Built in 1901 to house the Banco do Brasil’s city headquarters, the Centro Cultural Banco do Brasil (CCBB) (Rua Álvares Penteado 112, Centro, tel. 11/3113-3651, www.bb.com.br/cultura, 10 a.m.–9 p.m. Tues.–Sun.) is an opulent beaux arts building decked out with mosaic murals and crystal chandeliers that hosts a wide variety of cultural and artistic events.

Close by, the Prédio do Banespa (Rua João Bricola 24, Centro, tel. 11/3249-7180, 10 a.m.–5 p.m. Mon.–Fri.) was São Paulo’s answer to the New York’s Empire State Building. Inaugurated in 1947, this grand skyscraper—headquarters of the Banespa bank—remains one of Sampa’s tallest buildings. From the panoramic deck on the 35th floor, you are treated to impressive views of the city.

Prior to the Banespa building, Sampa’s tallest building was the elegant Edifício Martinelli (Rua Libero Badaró 504, Centro, www.prediomartinelli.com.br), completed in 1929.