I've taken advantage of the Intl Date Line on this one ...
Some years back, I left SIN on early morning 6am flight of on UA. Arrived in HKG on stopover. Caught afternoon HKG to SFO. Because I cross the IDL, arrived in SFO same day, morning about 9am or so. Went into the office for couple hours, caught an afternoon flight from SJC to ATL, stopping in SLC along the way.
I count 6 airports and who knows how many miles. Needless to say, I was beat. It was a long long day.