Thing the first: Where do I feel like going - is it interesting or have good bacon sarnies
Thing the second: Will the wx/conditions allow it
Thing the third: How long will it take - can I get an a/c for long enough to complete the trip comfortably
After that it's all pretty straightforward that's to say when those three criteria answered it'll usually dictate the destination
Ace currently praying for good wx and an aircraft so I can take the Texan Rimmers on a Pub StJean (LE2K) run on Friday