I like to follow my favourite sport teams around (NHL, OHL, MLB, NFL, and the occasional NASCAR race). I do this mainly with my PC-12 (from Flight1) and my PC-24 (from Iris). I've added dozens of freeware and payware airports and sceneries for all of the cities I hit. When there's a day or two between games I just fly back to my home airport.
To change things up a bit from time to time I do special tours. I've done a Capitol Cities World Tour with the PC-12. I completed a Canada 150 tour by hitting each provincial capitol and a tour of Route 66 with my DHC-2 Beaver (from Aeorosoft).
Right now, I have the Beaver sitting in Clearwater FL ready to follow the Toronto Blue Jays around Spring Training and when that tour is done, I'll be tracing the Mississippi River from Louisiana to it's headwaters in Minnesota. From there I'll jump it over to Vancouver BC and start a tour of the Trans-Canada Highway. All of my tours with the Beaver are done low altitude VFR.
As with my sports team following I look for (mostly freeware) airports and sceneries for my tours.