Brazil’s largest city can be overwhelming, but navigate the urban sprawl with a purpose and you’ll be a paulistano in no time. Start a visit with a guided tour of the incredible street art galleries, including the most famous graffiti display at the Beco do Batman, which gives the metropolis a dose of color and culture. Break for lunch in a café or “boteco” in the bohemian neighborhood of Vila Madalena. For a fun activity, swing by The Coffee Lab for a caffeine hit and a lesson in in coffee brewing (the café is also a school).
In the afternoon, opt for either a traditional Brazilian cooking class or head to Parque Ibirapuera, the city’s largest park, and one of the only respites from the urban landscape. For dinner, try Brasil a Gosto for traditional Brazilian cuisine or D.O.M. for a big night out. To partake in Sao Paulo’s vibrant nightlife, head to Hot Hot after your meal, which hosts a roaring electronic music scene.
Start the next day at the Muesu de Arte de São Paulo, which is especially fun on Saturdays, when a street fair sets up camp outside. After visiting the museum, stroll through the markets for one-of-a-kind mementos and delicious street food. In the afternoon, explore Avenida Paulista, which was once the business-center of the city, but now boasts a beautiful mix of grand architecture and upscale homes. The nearby Jardins neighborhood is the place to go for luxury shopping. Before heading back to your hotel, visit Edifício Copan, the contemporary building designed by Oscar Niemeyer that is now an apartment complex. The nearby skyscraper Edifício Italia has an observation deck with sweeping sunset views of the city.
For dinner, splurge on a feast at French-Italian Kaá or at high-end sushi spot Kinoshita. For something more family-friendly and low key, try the city’s best pizza restaurant, Braz, or the charming Chou, located in the Pinheiros district that's known as São Paulo's "new downtown."