Just remember the "6-months of use outside Florida" for any boat purchased outside Florida
- if you wish to avoid paying the Florida Sales/Use Tax.
Routing wise - I would suggest, considering that you do not have a mast
, that you head
down the Long Island Sound
to Manhattan then down the East River to New York
Harbor to Atlantic Highlands in New Jersey
When the weather
back up and around Red Hook and down the Atlantic coastline to Manasquan Inlet and the Pt Pleasant Canal south down the New Jersey
ICW. That will take you all the way to Cape May and consume a fair amount of time.
From Cape May Canal you enter the Delaware River and head north to the C&D Canal - maybe with a diversion to Philadelphia. The C&D Canal will take you to the Chesapeake Bay
and a lot more places to spend time until you get to Norfolk and the Atlantic ICW. From there to Florida there is no end of great and interesting places to stop and explore. However, you will be sucking up months working your way south if you take advantage of a lot of the great places to visit.
Leave a month before the Annapolis Boat Show
and then you can take in that event before it gets too cold to remain in the Chesapeake. When to leave is really dependent upon how many places you want to stop and explore. You can rough out your time by adding a day or two for exploring ashore every other day of underway running. But it is highly variable.