The flaw that I see (at least for the South Florida location), is that the most likely reason you would be "bugging out" would be a hurricane.I am not a prepper but since moving back to Long Island to take care of elderly family it has made me wonder about bugging out in a “bad” situation.
1. Assume health and finances are taking care of.
2. Living somewhere near large body of water (Long Island or South Florida)
3. Excluding a WW III scenario cause obviously there would be a whole other set of concerns.
Rather than bugout to a rural area or bug in somewhere in the suburbs what do you think about bugging out in a sailboat? From South Florida you could get to the Bahamas or most anywhere in the Caribbean to stock up on supplies or even Latin America. I know there are pirates etc but seems like this would give you some great advantages. You can carry fresh water and purify some as well. You could fish for food or simply go resupply somewhere in the Caribbean and buy yourself time and distance from the problem.
Just curious what you all think about the viability of such a plan.