Inspired by the challenges others have given them selves and talked about here; I thought it'd be neat to conduct one of my own.
I decided to fly from pole to pole; North to South. More specifically; from Alert on Baffin Island to McMurdo Station; Antarctica.
With modern instruments and your choice of weather conditions; it's really not too difficult; just time-consuming. So I decided 'what the hell; go all out'.

I decided on the following format: I'll fly the venerable DC-3; in the red-and-yellow paint scheme to aid in visibility in case I go down in the polar regions. For weight; in addition to myself and a copilot I'm carrying 2000 lbs. of gear (including survival equipment if required) and 1500lb. of spare fuel in drums in the back; just in case I can't reach an airport. Should I need to put down and use the spare fuel; it'll be added to the tanks and deducted from the weight, of course. Doing so will take 2 hrs.per 500lb.

I fly under full realism; with max autogen enabled; plus realistic weather on and set to update every 15 minutes. Also; I fly strictly from the VC; no extras - such as the status bar - enabled. Navigation is by ground alone; using the map beforehand to plot my next leg.
Whooo - this is gonna be tough!
Anyhoo; just finished the first leg; a short shakedown hop from Alert (CYLT) to Thule Greenland (BGTL). Distance; around 400mi. This was the one and only time I set the time; I set it for a noon takeoff - the rest will be system time. (Needed the visibility for an accurate shakedown - only flown the Gooney Bird twice before. LOL!) Time at touchdown; 14:18. Moderate to heavy turbulence encountered during the flight with poor visibility on approach into Thule - fortunately it cleared within 15,000' of the ground.
Hee hee - this is gonna take a while; but man, will it be fun! If you want; I'll keep you posted.
