In a travel destination so imposing in breadth and scope, you'd bet that the number of cultural attractions is going to be an accurate reflection. There are keynotes of Sao Paulo's history in every corner of the city; sadly, it's a let down that numerous European-style buildings and important landmarks have seen some level of degradation over the years. Don't let that deter you. There is enough historic beauty in Sao Paulo to shame many European cities.
It may be best to start your journey via Paulista Avenue, which connects downtown (where the city originated) and western Sao Paulo (where the modern highrises have taken hold). A sight to behold both day and night, this 2.8 km (1.74 mile) stretch contains hundred year old mansions side-by-side with contemporary skyscrapers, with highlights that include the renowned Museu de Arte, the Conjunto Nacional, and the pyramid-shaped Edifício Luís Eulálino de Bueno Vidigal Filho.
Although not as lovely as it once was, Centro is where you'll find a lot of the older architecture of Sao Paulo. The Praça da Sé is a great place to people-watch and stroll about, while the Praça da República is a square surrounded by a small group of famous buildings. Just don't expect a nicely preserved area; vandalism has been an issue in the past and still rears its head on a number of these historic buildings.
Nowadays, Sao Paulo's west region is the center of modern affairs, whether it is from the constant flow of workers during the week or the constant flow of nightlifers during the weekend. Your cultural sensibilities will be well catered to as well, since you'll find a ton of museums in this area (many university-related), and two areas where the world of modern capital has staked a claim, Brooklin Novo and Vila Olímpia. Explore these areas if you'd like a sore neck from constantly looking up.
Numerous other churches, museums, and other bearers of culture exist in other parts of this massive city, particularly in the wealthy South Central area and in the Southeast, where the Parque da Independência is home to the excellent Museu do Ipiranga (a can't miss in our opinion).
There is still much more to this city of 20 million citizens; these are just the highlights! Look through our culture listings and see more about what Sao Paulo, an often forgotten vacation destination, has to offer you.