This thread seems to a mix of a bucket list of "what" one wants to fly and "where" one wants to fly. My post is in the "where" category.
15 years ago, I got the thought in my head that I would like to fly around Canada. "Around" was a generic thought for a while but eventually morphed into "AROUND" Canada. Since then I have been planning and working towards circumnavigating continental Canada. This mean flying north to the Arctic Ocean near the Alaska-Yukon border and "hanging a right" and coming out on the northern shore of Quebec/Labrador. I am not planning going north around the northern islands such as Ellesmere and Baffin. That just seems a little ambitious
I had hoped to be the first to do that type of trip in an ultralight airplane but after a 2006 trip to the sub arctic (north of the Arctic Circle) in my Rotax 582 Beaver RX550, I realized that my not be so smart

Time to step up the planning.
I have spent the last 5 years plans building a Zenith CH750 with this goal in mind. I have decided that the CH750 is already slow enough that I want to do it on wheels; forget the floats. It will have about a 12 hour fuel range with a Rotax 912iS fuel injected engine and will have a fully equipped panel (glass). I have about a year left on my build project and then I will start working my way up to an experience level that hopefully will see me succeed in my goal.
Obviously, the northern portion of the circumnavigation is the most challenging part. I have been in the north enough (although not that far north) to know that weather, weather, and weather is the challenge. I will be under no schedule and I will be pursuing my instrument rating, although I plan on making the trip VFR. The 750 will not be IFR certified (but will have a fully capable panel) and I suspect CH750s don't like ice

Once I am flying I will be making several longer and longer trips into the north and I will be flying my wife across Canada to Nova Scotia and Newfoundland, as promised, very soon after getting this pile of scrap aluminum into the air
I am not really sure that it will ever happen, but it IS a goal, and working towards it has been fun so far.