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It's best to know someone from Sao Paulo to get by in the enormous Brazilian mega-city. To explore Sao Paulo, count on the must-see locations.
During the daytime, the centre of Sao Paulo swarms with people. Businessmen rush into the buildings and only leave in the evening, often after several hours of traffic jams up to their condominium, high-security residences with all services in the affluent suburbs. The city centre of Sao Paulo is disorganised. Following a map in Brazil's largest city is like a Chinese Puzzle. The Viaduto do Chá might be a good starting point.
You must start with lunch in the mercado central, a very pretty building, where you can try two specialities: the pastel de bacalhau (fish cake) and the sanduiche de mortadela (mortadella). Climbing to the top of the Altino Arantes Building, a building based on the model of the Empire State Building, will give you a breathtaking view of the city's skyscrapers. You will find the interesting gothic buildings in the old districts. In the historical centre of Sao Paulo, note the Patio do Colegio monument where the city was institutionally founded and the star Marco Zero on the parvis of the Catedral da Sé, a symbol of its development.
If you have the time, make sure you go to the beautiful Ibirapuera Park, with its lake, multicoloured birds and immaculately white buildings (auditorium, Oca pavilion etc.). The Pinacotheca of the Estaçao da Luz and the Japanese district of Liberdade are easily accessible by the underground.
You will notice that Sao Paulo is a rich city and is very developed. The buildings are guarded by security guards who monitor the arrivals and departures, penthouses flourish in the attractive districts, as do the latest shopping centres. The Shopping Cidade Jardim, from which you can see the Octávio Frias de Oliveira Bridge, is a good example, as are the shops on the Paulista Avenue where locals do their shopping. La Casa das Rosas is completely anachronic in the landscape.
Sao Paulo is undeniably a cultural city. The MASP, Museum of Contemporary Art, offers quality exhibitions and the small cultural centres offer numerous free exhibitions. It's also a city of intentional gastronomy because you will definitely find all the dishes you can dream about (Indian, Chinese, Lebanese and of course...French cuisines!). I recommend going to the chic Oscar Freire street to eat. Ideally, you would be invited to someone's house to try a feijoada with kidney beans and a little salt.
Vila Madalena is the boho district of Sao Paulo. In fact it's just an enormous roundabout where you will find adolescents on café terraces. The people of Sao Paulo go out very late. As the shops close at 21:00, it's common for them to go to their house to get ready then arrange to meet at 1 or 2 in the morning to go dancing. A card system allows you to pay for all your drinks at the end of the night... Dangerous for your wallet! To enjoy all of Sao Paulo's districts, you must allow 4 or 5 days. In a day, you will see the city centre but Sao Paulo will probably leave you with a bad impression.