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Share some of your most bizarre, unusual, complicated routings you've ever travelled from A to B. It could be a backtrack, itinerary with multiple stops, etc.
Here's my experience, it's not a long distance between the two cities, but it's a hell lot of travelling.
Back in June, a cousin of mine held a beach wedding in Penang, Malaysia. (How cliche 
) To get from Singapore to Penang, I could either drive, take the train or fly.
Driving
Driving wasn't ideal, as the journey would take at least 8 hours, and this does not include the ferry trip from the mainland (aka Butterworth) to the island. I could also drive directly to the island, skipping the ferry trip, but the bridge which connects Penang and Peninsular Malaysia has a reputation for traffic jams. Long road trips is also not my thing. Thus, driving is out.
Train
Next option, the train. Now, taking the train is not as easy as it sounds. Malaysia's train system is NO China's or Europe's High Speed Train system. The train from Singapore to Penang is not direct. When I mean not direct, I do not mean services with stops, what I meant was I have to take 3 separate trains in order to get to Penang, bringing the journey time to over 10 hours, not ideal.
Flying
Lastly, my family decided on flying. There are 4 airlines flying nonstop between Singapore and Penang. I was searching for tickets 2 weeks in advance. Silkair, as usual, was offering a costly amount of SGD200 return trip per person. Tigerair, a low-cost airline, was offering somewhere around SGD150 base fare, and that was only one way. 
(SIA what r u doing wif ur airlines) Jetstar has SGD140 base fares return, and AirAsia was $20 cheaper at SGD120.
However, I did some deep researching and found a unusual routing which was around SGD75 round trip (including additional ground transportation). Note that the flights are not under the same itinerary.
First, we took a taxi to Senai Airport in Johor Bahru, a city at the southern tip of Peninsular Malaysia, about an hour drive from Singapore.
We took a FireFly (a full-service subsidiary of Malaysia Airlines) flight to Subang (SZB), a secondary airport in Kuala Lumpur, for only RM40 per person (one-way). (A steal imo)
We had another flight booked on Malindo Air (for those of you who don't know, it's a full-service carrier) from KLIA (KUL) to Penang, which was RM80 per person (return). We had to transfer airports in Kuala Lumpur on the outbound trip, with 3 hours in between. The journey between Subang and KLIA took around 1.5 hours (depending on traffic). We took a coach service which costs us RM10 per person. Fortunately, we arrived at KLIA on time for check-in for our Malindo Air flight (thank god, if we did not we had to pay for us to get rebooked since these two flights are on different tickets, it's a good thing they moved from the overbudget "low-cost" 
klia2 terminal to the KLIA Main Terminal).
Fare for outbound trip per person : RM40 + (RM80/2 since it was a return fare) + (RM36/4 for taxi to JHB) + RM10 (Subang to KLIA coach) = RM99 or SGD32
Total travel time outbound : 1 hour taxi + 45 minutes at JHB + 45 minutes flight + 3 hour layover + 45 minutes at KLIA + 1 hour flight = around 7 hours (difference between driving not that much 
)
On the way back from Penang, we flew to KLIA on Malindo Air (since it was a return ticket) and had to self-connect ourselves (again, but this time at the same airport) to a Malaysia Airlines flight back to Singapore. We had a 2 hour layover (which is alright for an international layover). As usual, we made it on time for check-in and breezed through immigration queues with my Malaysian passport 
. The Malaysia Airlines flight costs us RM90 per person, which we think is worth it, since we're arriving into Changi Airport, aka the best airport in the world. 
(and costly taxes and service fees)
Fare for inbound trip per person : (RM80/2 + RM90) = RM130 or SGD43
Total travel time inbound : 45 minutes at PEN + 1 hour flight + 2 hours layover at KLIA + 1 hour flight = around 5 hours (somewhat huge difference between driving)
Total fare per person : RM230 or SGD75
Is the SGD45 difference worth this trouble? In my opinion, yes, since I get to travel on 3 different airlines and visit 4 different airports.
Sorry for this long post. 
I would love to read your bizarre routing experiences.
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