SAO PAULO IS GIGANTIC. It’s the largest city in the Americas with around 11 million residents and a few hundred different neighborhoods divided into five zones (east, west, central, north and south). You could live here all your life and not see half of it.
In a way, this is where São Paulo began. At the Hospedaria do Imigrante (Immigrant hostel) now turned into the Immigration Museum, some 70 different nationalities first arrived in the city: Italian, Portuguese, Armenian, German, Japanese, Turkish, Syrian and others, running from war, plague or religious persecution. To this day Mooca has a strong Italian vibe, with countless cantinas and pizza places, like Pizzaria do Angelo.
São Paulo’s hippest area is currently facing intense gentrification, slowly losing its hippie charm, and turning into a bunch of office modern office buildings and hipster cafes. A way to get a grip of the area is walking the graffiti lane Beco do Batman (the city’s most Instagrammed place) and walking up Harmonia street toward Rodésia street. Turn right until you reach bar/bookstore/small market Mercearia Sao Pedro, where you can have a simple buffet lunch washed with cold beers on the sidewalk.
Vila Madalena’s older and cooler sister, Pinheiros is a mixed zone of interesting shops and all kinds of services and restaurants. The most interesting area is what people are calling “Baixo Pinheiros,” around the old Pinheiros market, currently going through a moment of rediscovery. Arrive before noon to taste fresh ceviche prepared by chef Checho Gonzale at Comedoria Gonzales on the first floor. After, walk up Artur de Azevedo, crossing all the neighborhoods, and have the best ice cream and coffee combo at Frida e Mina, on the corner of Joaquim Antunes street.
The biggest Japanese community outside of Japan is in São Paulo. Immigrants started arriving in the early 20th century, establishing themselves in what’s known today as Bairro da Liberdade. The area is a cacophony of Japanese/Chinese/Korean stalls selling greasy food, manga, cosmetics, fake branded clothes and cheap house supplies, with surprises to be found by those willing to explore. The open-air food market on weekends right on the exit of the subway station is getting too crowded — skip it for beers at Kintarô, a small, very simple joint run by a family of sumô wrestlers. Or have fresh sushi at the oldest Japanese restaurant in town, Hinodê. They’re both in the same street, Tomas Gonzaga.
Centro is a chaotic, sometimes dark area, but it is also where São Paulo’s best architecture and street art is. Use the subway system and come on weekends to avoid crowds. Shop for vinyl records at Galeria Nova Barão, have michelada at La Central (on the ground floor of the iconic Copan Building) or climb to the top of São Paulo’s first skyscraper, Edificio Martinelli. If you want to have a taste of old São Paulo, Teatro Municipal and Centro Cultural Banco do Brasil will give you an idea of how glamorous and grand the city was during the coffee barons period.
Walk down Augusta Street toward the city center and you’ll hit Baixo Augusta. There was a time when people only went that way looking for brothels and prostitutes. They’re still there, but now they share space with countless nightclubs, bars, cheap eats, and shops. Paulistanos call the area between Avenida Paulista and Praça Roosevelt Baixo Augusta — a neighborhood that doesn’t sleep between Thursday and Sunday. Try arriving on an early Friday night at Ibotirama for beers — as Paulistano as can be. And don’t miss the thrift store turned live music bar Caos Augusta.
The most Paulistano of all places, Paulista Avenue was where coffee barons had their mansions. It’s since turned into the financial heart of São Paulo and now is its commercial center. It’s a place for meetings and the extra-official lane for protests in the city. On Sundays, when the avenue is closed to cars, São Paulo’s heart beats stronger. Come to see the world class MASP art collection, right in the middle of the avenue, and maybe see a film for free while sitting on the nearby stairway of Mirante Nove de Julho (you can see it from MASP’s windows).
Walking west down Augusta Street away from Paulista you’ll reach Jardins. It’s nice for a stroll; these are the city’s most elegant streets. There’s some cool architecture from the 50s/60s, as well as classic restaurants like A Figueira Rubaiyat and the epitome of São Paulo chic: Baretto bar inside Fasano hotel. World famous “plastic shoes Melissa” make for a great present, but even if you’re not buying anything, visiting the art gallery/shop is an experience.