What comes to mind for me is doing low-level scientific research over Antarctica in a DC-8 based out of Punta Arenas, Chile (Google Operation Ice Bridge).
The next happy memory is flying to/from Alaska VFR in a 185 via the Cassiar Hwy and/or the Trench, with excursions to Skagway and Haines, AK. Nice folks and scenery in BC and YT. 13 trips in 14 years, and the fun meter still pegs. Hard to beat a high wing taildragger in the mountains, i.e. flying in the shade with a great view, and do I make a wheeler or a three-pointer? What's not to like?
To be fair, it's not all roses. Canadian avgas prices are OPPRESSIVE, especially at Whitehorse.
