Drop your bags at one of the many affordable hostels in the Paulista district - the most LGBTQ tourist-friendly area in town.
Once checked in and settled, go for a walk in the Jardins area or the Frei Caneca street nearby.
Get a extremely well-filled Hot-Dog Brazilian style at the the Black Dog eatery or a pastel, a traditional local fried pastry in one of the street stalls around (Try the pizza pastel - it's particularly tasty).
For drinks, head to Athenas bar for ice cold beers and cocktails and tapas-like portions. But arrive early as it get super busy from the afternoon happy hour until late. Ask for an outside table, weather permitting.
Bella Paulista Bakery close by is open 24 hours and has a good selection for breakfast, lunch or dinner.
A good club in the area is 'A Loca' with its themed nights during the week.
Once on Paulista Avenue, stop at the MASP 'gap' and head towards the end of the piazza for a view of the city-centre skyline.
Across the road is the Trianon Park, a very good option for a pit-stop and nature, a break from the city hustle. Note that the park closes overnight, and male escorts offer their services in the area.