Avenida Paulista

One of the most expensive strips of real estate in Latin America, Avenida Paulista is São Paulo’s most iconic thoroughfare. What started out as a residential street lined with the ornate neoclassical mansions of 19th-century coffee barons has, in a little over a century, turned into an urban canyon of glass and steel and a modern hub of business, culture and entertainment.

Anchored on one end by busy Shopping Paulista mall and on the other by multi-use architectural standout Conjunto Nacional—vaguely reminiscent of the famed congress building in Brasília—, Avenida Paulista serves as the address for many of the city’s most important cultural institutions, including the São Paulo Museum of Art (MASP), lush Parque Trianon and the Casa das Rosas arts center (located in one of the last mansions remaining on the street).

Though several hundred thousand denizens file into Avenida Paulista’s office buildings every weekday, the street remains lively come nightfall, when restaurants and nightclubs along cross-streets in the adjacent neighborhoods of Jardins and Bela Vista fill with diners and party-goers. Anything goes on buzzing Rua Augusta, one of the city’s liveliest nighttime haunts, and even more goes on Rua Frei Caneca, epicenter of São Paulo’s gay and lesbian scene. Sunday afternoons, craft fairs and flea markets spring up at the foot of the MASP as families stroll along the strip, and throughout the year, big events such as the world’s largest gay pride parade (May/June), the renowned São Silvestre road race (December 31st), and New Year’s Eve celebrations bring a few million people into the area.