Question 1 – What are you trying to escape?
Question 2 – Do plan to re-enter later?
Question 3 – Where will you go?
Question 4 – Would it be better to be “caught” for now and “escape” later?

Good points Robin.
Event that I described actually happened (more then once) in small village (coast) in period where law was more or less absent, or even when some kind of law was there “actions” like plundering were even encouraged in a way.

Guy had information right on time about units (paramilitary groups of different kinds) coming to the village, and he simply took small boat and paddle behind small islands, rocks actually not so far from the place, and wait there to raid to be done.
It was happening during the night time, in time when as I said organized groups simply go in night time and steal (and beat and kill) from unprotected villages.

Obviously it worked for him, but as I said every situation is specific. This was maybe more case of luck and right mindset.
Fact that someone is living on coast (or next to river or similar) is I think enough to have some kind of boat in preparations, everything else depends on specifics.

About “Would it be better to be “caught” for now and “escape” later? ” question, no, from my experience definitely no, but it is my experience.