One of the special things about São Paulo is its rich mix of cultures that coexist in a hulking metropolis that is one of the only truly cosmopolitan cities in Latin America. The ethnic, social, and cultural background of the city is made up of over one hundred years of immigration from different parts of the world, largely after the abolition of slavery. One such immigrant community which has flourished in São Paulo is the Japanese, with the city having the largest population of Japanese people outside of Japan itself. Nowhere is this more apparent than in the neighborhood of Liberdade, São Paulo’s very own Japantown.
Start your first day off by exploring Liberdade, with its East Asian-inspired design and architecture and traditional Japanese stores and restaurants. On weekends, the neighborhood hosts an arts and crafts festival where visitors can purchase classic Japanese ornaments and trinkets, as well as some delicious street food. Liberdade is also home to other East Asian communities in São Paulo, and Chi Fu, arguably the city’s most famous Chinese restaurant with excellent food, huge portions and Kill Bill-esque décor, is a great spot to have your first lunch.
Once the sun goes down, head over and grab a booth at Izakaya Issa, a classic Japanese izakaya (informal sake bar) with some of the city’s best food. Afterwards, you only really have one choice for a night’s entertainment in Liberdade: karaoke. São Paulo loves karaoke, and all the best bars are concentrated within Liberdade’s streets. Chopperia Liberdade is a superb option for the full São Paulo karaoke experience, with kitsch décor, drinks which pack a punch, and an envious selection of music from around the world (make sure to ask for the livrão, the big book). If singing in front of strangers isn’t your thing, you can rent karaoke booths at Porque Sim, where the staff will bring drinks and food straight to your private room.
If you can manage it after a night of singing and dancing, get an early start on day two and head up to the Núcleo da Pedra Grande, part of the Cantareira State Park to the north of the city. After a brisk hike to the top of the trail, you will be rewarded with one of the greatest possible views of São Paulo, looking down upon its sea of skyscrapers from one of the highest spots in the metropolitan region.
Afterwards, to wind down after your morning hike, head to the hip neighborhood of Vila Madalena and grab a seat at Coffee Lab for a superb cup of joe. With your batteries recharged, take a saunter around the neighborhood and check out Beco do Batman (Batman’s Alley), where you can see amazing examples of São Paulo’s vibrant street art scene. Make sure you bring your camera, as the pieces are constantly being renewed and replaced.
When it’s time for the sunset, head over to Sunset Square, otherwise known as Praça do Pôr-do-Sol, in Alto dos Pinheiros. This green space is frequented by people of all ages at the end of every day for its incredible sunsets.
São Paulo’s historic center is one of the most unjustly overlooked parts of the city, which is precisely why you should dedicate an entire day to soaking up its invigorating atmosphere and gorgeous architecture. Tourists often stay away from Centro as they have been told by locals it is dirty and dangerous, but while it is certainly grittier and more rugged than the rest of São Paulo, it has charm and history which is hard to find in the rest of the city. Start your third day in São Paulo’s Municipal Market, the Mercadão, and marvel at the hundreds of stands and their amazing selection of rare fruit and vegetables. Buying fresh produce from the Mercadão is actually quite expensive, but the sellers will let you try as many samples as you like without an obligation to buy. Before you leave, head upstairs and grab one of the market’s famous foods: either the gargantuan mortadella sandwich, or the pastel de bacalhau—a truly delicious deep-fried thin-crust pie filled with salt cod.
After leaving the market, take a walk around the historic center and soak up the city’s history through some of its major works of architecture (try following this guide). For dinner, while you can certainly find somewhere upmarket, try one of the simpler and more traditional restaurants the center has to offer, such as Peruvian place Rinconcito Peruano, which is already a São Paulo institution, or the charming Middle Eastern spot, Vovô Ali.
As night falls, it’s time to go clubbing. São Paulo’s nightlife, with its wealth of alternative cultures, spontaneous organizing, and parties which go on all night (and well into the following day), is one of the best on the planet. Trackers, Alberta #3, Casa da Luz and L’Amour are all solid options if you’re staying in the historic center, while D-Edge, over in the neighborhood of Barra Funda, is a world-famous electronic music club.
On your way home, do as the locals do and stop by traditional São Paulo diner Estadão and pig out (pun most certainly intended) on one of their incredible pork sandwiches.
Work off your inevitable hangover with a nice walk and an ice-cold coconut water at Ibirapuera Park, voted one of the world’s best urban parks. Ibirapuera is usually packed during the weekends, but the grounds are so vast that you can always find a quiet spot for a picnic or a well-deserved nap in the sun. Make sure to check out the park’s museums, especially the Afro Brasil Museum.
Once you’ve got the museum bug, head over to Paulista Avenue, the city’s main thoroughfare, which on Sundays is closed to traffic, making it a form of urban beach with families walking their dogs, cyclists, and lots of musical and cultural displays. Walk down to São Paulo’s leading art museum, the São Paulo Art Museum commonly known as M.A.S.P. Housed in an impressive building designed by iconic Italo-Brazilian architect Lina Bo Bardi, its four columns are raised above the ground, giving it the impression it is floating above the street. Later, take a walk down to the leafy and swanky neighborhood of Jardins and check out Rua Oscar Freire, Latin America’s most expensive shopping street with stores from all of the world’s top designers. For dinner, head to Tordesilhas, one of the best spots in São Paulo to get a taste of the amazing variety Brazilian cuisine has to offer. The house specialty is a classic Amazonian dish called tacacá, a seafood broth made with a manioc extract called tucupi, jambu (a green leaf from the Amazon that numbs the tongue), and dried shrimp. Tacacá is served hot, but gives an oddly cooling and refreshing sensation upon eating.
For your last day in São Paulo, it’s time to get to know one of São Paulo’s (and Brazil’s) most important traditions: soccer. While the sport is huge all over the country, people in São Paulo take futebol (as it is known in Brazil) very seriously indeed. Experiencing soccer in the city is an excellent way to get an insider’s view of the São Paulo way of life and the city’s traditions. Start the day off by going to São Paulo’s municipal Pacaembu stadium, a gorgeous temple of football which hosted games at the 1950 World Cup. Inside the stadium there is an excellent soccer museum which is a great day out both for fans of the sport and those who are looking to learn a bit more about futebol.
Then, in the afternoon, it’s time for the real thing. São Paulo is home to three massive soccer clubs (São Paulo F.C., Corinthians and Palmeiras), who each have their own stadiums, and on any given weekend at least one of them will be playing in the city. Tickets can be complicated to buy for tourists, but there are independent tour guides who can help.
After the match, finish your five-day stay in São Paulo by trying one of the city’s favorite foods and a matter of local pride: pizza. Paulistanos claim that they have the best pizza in the world, and after trying one, it’s difficult to argue with them. There are so many places to choose from. If you are looking for some of the best true Neapolitan pizza, head to Leggera Pizza—which is one block away from Palmeiras’ Allianz Parque stadium—for some typically São Paulo-style pies, try Speranza, or one of the city’s favorites, Bráz Pizzaria.