Milan is 5 hours ahead of São Paulo. Put the other way round: São Paulo is 5 hours behind Milan.
São Paulo is UTC-3 in summer and UTC-3 in winter; Milan is UTC+2 and UTC+1.
Working 09:00 to 17:00 in both cities leaves 3 hours in common: 09:00 to 12:00 in São Paulo, which is 14:00 to 17:00 in Milan. Those are the hours to aim a call at.
Milan changes its clocks for summer and São Paulo does not, so there is no single answer: the gap is 5 hours for the northern summer and 4 hours for the rest of the year.
| São Paulo | Milan |
|---|---|
| 08:00 | 13:00 |
| 09:00 | 14:00 |
| 10:00 | 15:00 |
| 11:00 | 16:00 |
| 12:00 | 17:00 |
| 13:00 | 18:00 |
| 14:00 | 19:00 |
| 15:00 | 20:00 |
| 16:00 | 21:00 |
| 17:00 | 22:00 |
| 18:00 | 23:00 |
This page covers one pair. TimeGap takes a list: add every city you care about, drag one marker, and every row reads the same instant on its own clock. It marks the hours you would actually take a call, finds the window where the most people are reachable, flags public holidays, and puts the time you pick straight into Outlook or Google Calendar.