Paulista Avenue in March

April through September gives you the best weather – less rain, cooler temperatures around 20°C, and clearer skies for those Instagram shots from MASP's terrace. The São Paulo Art Biennial happens every two years (next one's in 2027) and transforms the city into an art lover's paradise. Avoid December through February unless you enjoy getting soaked – São Paulo's summer brings daily downpours that flood the streets. Winter (June-August) means you can actually walk outside without sweating through your shirt. The Virada Cultural in May shuts down the entire city center for 24 hours of free concerts, theater, and art installations. Book hotels early during Fashion Week (usually October) when the entire fashion industry descends on the city.