I had been to Sao Paulo once before and barely remembered anything. It was a quick trip for work (does anyone go to Sao Paulo on vacation?) And this trip was much the same, except I got a day extra to visit and enjoy the city.
The Paulistas, as they’re known, are fashionable and friendly. It’s a very cosmopolitan city, but not without it’s challenges. I noticed a pretty big discrepancy in neighborhoods even just walking a few blocks. There are a lot of warnings on the internet on safety, but I managed fine in the places listed below, and even walked around the hotel after dark (apparently a no-no).
Language was a little challenging, especially since I had to go buy some work supplies at an art store for a specific kind of material that didn’t translate too well into Portuguese.
This is more of a checklist than specific recommendations. Brazil has great food overall, but you should definitely try Pao de Quiejo (little cheese breads), Fejoida (black bean and meat stew), fruit juices, fruits, and meat of any kind.
Parque Ibirapuera: Sao Paulo’s “Central Park” is massive, with ponds, walking trails, and coconut water vendors lining the walkways. There are a few museums inside. I checked out the small Museum of Modern Art.
Morumbi Shopping: A legit shopping center near the Grand Hyatt with upscale shops and excellent restaurants on the lower floor.
Rua Oscar Freire: An upscale shopping street in the Jardim Paulista neighborhood with great boutiques and good people watching.
Grand Hyatt: Great hotel–good location (it was near my client), spacious, modern rooms with great bath products, a good Japanese restaurant, and well-equipped gym and pool.
Japantown area: I was disappointed in the weekend market. I was expecting more, maybe? It was one road and a small craft market. It looked like there were some good restaurants, but I visited too early to be hungry.