I did a six-flight trip once (one overnight stay involved due to final flight being on an EAS leg), with 56 hours, I think, of traveling. Could have pushed it to 7 if I hadn't already been at the one international airport in the origin country, and I could have cut the EAS leg out if my family had driven 2 to 4 hours each way to be able to get me at a larger airport. Friend of mine did a trip that required, I think, 9 flights once. (from somewhere in the Alaskan bush to BDO)
I think anytime I have to flight with multiple flights over 4 hours is brutal. I've done ATL-DXB direct flights with a flight on both sides of that, and I've done ORD-DXB with a stop at LHR or FRA with an additional flight on both sides. I'd much rather have one 15 hour flight than two eight hours. On the 15 hour you can sleep some, maybe get a little ahead of jetlag if your timing lines up well. On the eight hour, you just get abbreviated naps, no sleep cycle, and you might think, oh, but you can get out and stretch your legs, usually what ends up happening is you get stuck going through customs somewhere and stand in line forever, then cram yourself into another plane. Give me one flight.
My worst was 42 hours (with an 8 month old baby) going from the US to New Zealand via Australia. It included an unscheduled 10 hours in SYD due to Virgin Australia not understanding visa regulations for New Zealand. VA tried to have us sent back to the US and Australian customs ended up giving the airline a five figure fine due to how long they delayed us. The thought of another 15 hour flight with a baby after 38 hours was not a happy one...
Not flying, but my worst travel experience ever was a 30 hour bus ride from Ouagadougou to Cape Coast. It's normally a bit shorter, but our bus was held up by highway robbers, who took all of my money.
Haha, I was originally going to comment about how you can always find a topper online. But in my case I get the story (no one was physically harmed, at least, and the police got there quickly). I'll take that over op's 81 hours of airline travel.
The cheapest one-way ticket from HNL to CEK (Chelyabinsk) tomorrow costs $2100. Getting there as quickly as possible (so leaving today and taking only 35h to get there) costs $3k.
Source: your favourite meta-search. And since I work for one, I won't link any :).
He's probably just a Russian who got disturbed on his vacation, you might be overestimating the excitement.
If we're sharing, my longest one to date is:
Cuzco - Lima (long layover, we got to visit Museo Larco and eat pizza) - Panama - Dominicana (technical stop, but we had to disembark) - Frankfurt - Moscow.
It was pretty painless, I only regret missing one lunch by being asleep.
As alluded to in the stack overflow comments, Carl de Marcken (ITA Chief Scientist) wrote some code to determine the longest possible shortest path between two airports with scheduled flights. At that time (circa 2000) the answer was Wasu, New Guinea to Peawanuck, Ontario. The best you could do was something like 48 hours and involved a very large number of flights. On a bad day the best you could do was over 90 hours.
Maybe somebody at Google could run the lisp function that computes that on current data and post the answer.
Typically a single flight number can only accommodate 4 legs/segment one way as this is a limitation in most GDS systems. Of course a ticket buyer can combine flights to create more legs if necessary but airlines don't schedule more than 4. 4 leg flights are not common however. A leg/segment is defined as a takeoff and landing. So a 4 leg flight would be A to B to C to D one way.
The longest flight I did was when I returned from a visit to New Zealand in 2004:
Invercargill -> Christchurch -> Auckland -> Los Angeles -> London LHR -> Edinburgh
The journey took around 36 hours and was largely uneventful. What I did learn was to check your baggage weight allowances; I ended up wearing quite a few of my clothes on the Invercargill to Christchurch leg :)
The Invercargill flight wasn't on my original itinerary as I thought I'd be driving up to Christchurch to catch first leg. So when I rolled up at the Invercargill check in I got a surprise:)
In Northern Canada, flights are chained. This means that to go from Old Crow (YOC) to Whitehorse (YXY), you need to do:
1. Old Crow (YOC) -> Inuvik
2. Inuvik -> Dawson City
3. Dawson City -> Whitehorse
Even getting to NY from there adds another two stops:
4. Whitehorse -> Vancouver
5. Vancouver -> Newark
Supposing you wanted to go to the Galapagos, the shortest trip from Yellowknife happens to go through Newark/New York City (yes, you'd need to change airports):
6. New York City -> Guayaquil
7. Guayaquil -> San Cristóbal Island
But you could probably find better results if you looked to leave the western hemisphere and go somewhere like VOG (7 segments total), UTN (8 segments total), or TMR (8 segments total).
Don't have to be particularly obscure cities to get a lot of segments. I once had to take a last minute flight from Cape Town to Seattle (before the direct Jo-burg to Atlanta route existed).
Cape Town > Johannesburg > Amsterdam > Atlanta > Seattle.
4 segments... and about 40 hours... gooooooood times :)
I think anytime I have to flight with multiple flights over 4 hours is brutal. I've done ATL-DXB direct flights with a flight on both sides of that, and I've done ORD-DXB with a stop at LHR or FRA with an additional flight on both sides. I'd much rather have one 15 hour flight than two eight hours. On the 15 hour you can sleep some, maybe get a little ahead of jetlag if your timing lines up well. On the eight hour, you just get abbreviated naps, no sleep cycle, and you might think, oh, but you can get out and stretch your legs, usually what ends up happening is you get stuck going through customs somewhere and stand in line forever, then cram yourself into another plane. Give me one flight.