Best I ever did was:

Toronto - Winnipeg by train - timetabled for 34 hours (or was it 32 with time differences) - was over 4 hours late in any case. Couldn't sleep a wink, I think it was another 6-7 hours before I actually got some sleep.

That was part of a journey across Canada by train, of which I got my monies worth. In that month I totalled over 3,000 miles by train, in standard coaches with a lot of sleepless nights.

The return plane journey was worse. In order to get the cheapest flights, and complete disregard for time zones, we managed to end up in Toronto airport for about 11 hours. We were up at 4am Vancouver time, to fly to Toronto, we flew out of Toronto at midnight that night, landed in Dublin the next morning. Didn't get asleep then till that night. Never felt worse in my life. Air transat was cheap, 80euro fare Toronto to Dublin, but Ryanair planes have more leg room. Really uncomfortable.