I've singlehanded this trip a number of times, always outside except for the first time when I went inside from Norfolk to Beaufort. If single handing, think NY Harbor to Cape May. You can anchor off the Coast Guard Station (but not too close), then Cape May to Norfolk. You could leave the boat there in a slip if needed and return for the next leg. Norfolk to Beaufort on the inside can be a pleasant trip (but once is enough) and keep going outside on to Charleston, where you could leave the boat again in a slip. Then to Fernandina Beach (I go to Canaveral, but I have a sloop so the docking is easier as there is no where there to drop an anchor, that I know of). Then on to Ft Pierce or on to Palm Beach or just go straight on to Miami depending on how you feel and how many days you brain can stay alert with just cat naps. Bear in mind that there is much more ship traffic (and fishing and barges in tow) on a trip like this than if you were off to Bermuda or the Caribbean, so staying alert really counts. Also, I never, never make night landfalls. As such, I plan my departure times based on making arrivals in the AM. (e.g I departed NY Harbor at 4 PM for an AM Cape May arrival) More often than not, I am taking a reef to slow the boat at midnight so as to not arrive at a port before dawn. The stopping off points mentioned are based on both nautical criteria and airport locations.

As to shoaling, I don't know of any areas except that there is an exclusion zone near Canaveral that is clearly marked on the chart. Once you get to south Florida you can stay safely off the shore but inside the Stream. And after the colder legs from the north, you'll love the sunshine and air temp.

Jon will also have valuable input, and hopefully he will provide his thoughts as well.

I will inquire has to the various options for you here in Miami. The fact that you are a cat can complicate thing, but I'll have the info to you in the next few of days.

Cheers,
Ron