By Walker Dawson

With 31.5 million people in the combined metropolitan area, São Paulo is an impossible city to describe in only a few short words. To call it the New York of Latin America wouldn’t do this megalopolis justice.  Three times the size of Paris, this city would take several lifetimes to get to know.  São Paulo is expensive and crowded, but any city this large will naturally have its negative aspects, but if one is prepared to look beyond these, the positives far outweigh the negatives. São Paulo is a city of distinct neighborhoods and diverse lifestyles intermingling everyday on the subway and in the crowded streets, at the numerous bookstores, bars, nightclubs and restaurants.  Economically, Brazil is one the most unequal countries in the world, yet it is this exact inequality that makes São Paulo so complicated, yet so intriguing. The poorest and the richest of Brazil interact in close quarters, creating a complicated fabric from which emerges Brazil at its most creative and most intellectual. On par with New York and Paris, this is truly one of the world’s greatest and most captivating cities.  Many people overlook São Paulo for the beaches of Rio, or the jungles of the Amazon, but they are missing out on a city that has the ability to humble even the most seasoned traveler.

#5 Barra Funda

Barra Funda is an up and coming industrialized area northwest of downtown, characterized by art galleries and music venues of all types. The slightly rundown streets exude a type of Williamsburg-before-it-was-cool vibe. In 5 minutes, you can walk from D-Edge, one of São Paulo’s trendiest night clubs to Boteco Pratododia, where an alternative crowd dances to Caribbean salsa and other Latin beats late into the night . Not only is Barra Funda filled with an insane array of nightlife options, it is also a center for up and coming artists. Many of the industrialized warehouses are becoming independent studios such as Galeria Fortes Vilaça, which recently hosted an exhibition on the world famous São Paulo graffiti duo, Os Gemeos. Make sure to see what’s on display and check it out.

#4 Liberdade

São Paulo is a city of immigrants and that diversity can best be seen in Liberdade, a densely packed neighborhood of Japanese restaurants, Chinese markets, and narrow, hilly streets that light up beautifully at night. Brazil has the largest concentration of Japanese people outside of Japan, and the majority live in this neighborhood. The best way to discover Liberdade is to attend the wonderful Sunday street market, where you can buy the Japanese delicacy, takoyaki, a ball of octopus, shrimp, tempura flakes, green onion and ginger fried in fresh cream.  No one should leave São Paulo without having a meal at Aska, a cozy, Japanese ramen joint, that has super cheap prices (extremely unusual in this city), delicious food, as well as a long wait. A São Paulo must!

#3 Centro

Centro is the historic heart of the city.  Most Paulistas dismiss the the neighborhood as dirty and crime ridden, but if you are able to see beyond its decay, it is a fascinating area full of pedestrianized streets, 400 year old churches, steep hills with narrow, bustling streets, open-air markets, neoclassical and art deco architecture, and enough energy to impress even a hardened New Yorker. One of the most interesting aspects of Centro is its alternative edge. Most downtowns in North America are strictly about business, yet here in São Paulo, there are numerous alternative art galleries, and underground bars where skateboarders, weed smokers and anarchists rub shoulders with businessmen getting off of work. Be sure to check out Galeria do Rock, a five story mini mall dedicated to punk and skater shops, tattoo parlors and musky record stores.

The area around 25 de Março is considered the largest commercial center in all of Latin America, and is one of the best places in the city to see São Paulo’s diversity. Chinese and Korean merchants sell electronic goods to Bolivians and Paraguayans, while Syrians, Iraqis, Palestinians and Lebanese folks sell clothes and produce to every other race under the sun. One location that perfectly encapsulates the alternative-meets-business feel of Centro is a bar called Papo, Pinga e Petisco, a bohemian joint that wouldn’t be out of place in the most intellectual corner of Greenwich Village. Take a seat in the back behind the pool table, where the smell of African incense and marijuana mix with the aroma of dusty vinyls, books and dark Paulistânia beer.

#2 Vila Madalena/Pinheiros

Vila Madalena and Pinheiros are two trendy, residential neighborhoods adjacent to each other, located southwest of Avenida Paulista. While there aren’t many specific sights to see, its the best place in all of São Paulo to eat and drink. The coolness factor in these two hoods is unmatched anywhere in Brazil, and is on par with the the most hip neighborhoods of New York, Paris and London. Take a stroll down Beco do Batman, an old alleyway that has been converted into a space highlighting local graffiti artists. You won’t go wrong pulling up a chair at any bar in Vila Madalena/Pinheiros, but be sure to start with Mercearia São Pedro, which is part bar, part restaurant, part bookstore and part video store; definitely one of the coolest places in this city. Another great bar is Empório Sagarana, a perfect place to sample every type of cachaça imaginable.

For food, be sure to eat at Meats, an American style diner serving incredible burgers such as the Big Apple, a juicy patty topped with crisp green apples and a honey-wasabi glaze. Wash down your meal with a Guinness and Jack Daniels milkshake. For a slightly lighter meal, check out Kebab Paris, one of the best kebab places this side of the Atlantic. You also won’t go wrong at Feed Food, a stylish organic restaurant serving all types of world food in a greenhouse setting. For coffee, check out Coffee Lab, where baristas in lab coats serve aeropressed coffee for maximum flavor and kick.

#1 Bela Vista/Paulista

Avenida Paulista is the beating heart of São Paulo. While some might disregard the area because of its endless sea of skyscrapers, you only need to pause for a moment to observe the chaotic energy unmatched anywhere else in Brazil. As the sun sets and rush hour begins, artists line the street to sell their work, while musicians of all ages play for the teeming masses of businessmen. In one minute I witnessed a band play Creedence Clearwater while a separate group of Anarchists and Feminists blocked traffic while marching down the middle of the street.  Along Avenida Paulista, relax in a bean bag at Livraria Cultura, the largest bookstore in Brazil.

Adjacent to Avenida Paulista is Bela Vista, whose main thoroughfare, Avenida Augusta, is full of bars, restaurants, movie theaters, comedy clubs and music venues. The neighborhood was once inhabited by punks, skinheads, lesbians, gays and hippies, but today vestiges of the old neighborhood are mingling with business folks who trickle off Ave Paulista in search of drinks, dinner, and more. The contrast between the alternative original nature of Augusta and the recent wave of gentrification is a fascinating.  When in Bela Vista/Augusta, be sure to check out Chicano Taqueria, a new California style taqueria serving up mean burritos, tacos, quesadillas and San Francisco’s finest, Anchor Steam beer. Afterwards, hit up Caos Bar, an eclectic biker bar sporting Americana kitsch and serving up great drinks while you lounge on antique couches.