All in Y: YYZ/FRA, 10 hour layover...left airport and went to Mainz to tour the city) and then another overnight flight to JNB, 3 hour layover and then onward to PLZ. Something like 36 hours.
Also in Y: Once I did YYZ/GRU, 6 hour stop over, onward to GIG. Wildcat strike air traffic controllers closed the Rio airport. Didn't want to venture out to downtown Rio (small airport hotel sold out) at 23:00 so I stayed at the airport. Next AVAILABLE onward flight to SSA was late afternoon so this one turned out to be 40 hours.