Choosing destinations

When you fly for pleasure, how do you select your destination for a flight?
How long a flight do you prefer, ideally? How close do you remain to your
home base (if any)? And do you prefer to fly alone, or do you like to have
passengers? In the latter case, whom do you usually bring along?

Also, please indicate whether you own your own aircraft or simply rent one, as
this presumably has an influence on the choices above.