KEYW
I've done it both East coast and West coast, if you want it easy then you could do it on the West coast. You could effectively get out of Orlando and not speak to anyone until you get to Key West and speak to the US Navy. Although there is not much to see after Everglades City and there is no beach if the engine fails.
The East coast would be a little more challenging but Miami may vector you around as they don't want you near them on occasion.
Marathon is the best place to stop for fuel, it is way cheaper than KEYW.
The Navy will want you on the south of the Keys and yes probably over the water too, just remember KEYW is the small strip to the west, however inviting the Naval Base looks don't set up for finals, THEY WON'T be HAPPY!!
It's a great trip, have fun!!