Hugh,
Living in a coastal city on the northeast has had me thinking of bugout boats for some time. A cabin cruiser with supplies and full tank would make for an expedient exit from a burning city.
Having a retreat to arrive at would beat trying to make it on the boat à la “waterworld”. Sadly the logistics are daunting. A year around-maintained boat is not easy in a zone 5 climate, plus a maintained retreat to arrive at and then trying to make it in your “new home”.
As mentioned in numerous survival articles, you will most likely not be welcomed unless you spend some time living in said retreat. It’s not impossible but not easy if you have to maintain a full-time job and keep your family happy. Right now they may put up with your survival plans; however, make them sacrifice some material things to fund the bug out plan and life at home could get ugly.
I don’t see pirates in the equation for sometime after SHTF, but the Somalians have proved it doesn’t take much to be successful. My plan is 12-gauge slugs aimed at the waterline and .223 aimed at the cabin area. Most light craft here are made of fiberglass, and shotgun slugs should make quick work of the hulls. Of course, you would need a hardened position on your vessel to survive a gun battle.
If you were in Miami and had a cat to sail off in, it might suit your purposes. My plan is to head north and make landfall away from the cities. In a warmer climate maybe an island, but again you have to deal with caching supplies and unfriendlies. – UG