Welcome aboard, you'll find Gord May a source of lots of useful info.
I'm an Alaskan, now retired and cruising in the Sea of Cortez
, who had to go to Seattle
to find a decent boat
(the Inside Passage
trip back to Juneau made up for it). If you spend a lot of time in Florida
you'll find more to choose from, at better prices, when you get ready to buy your cruising dream boat
. You're also in a great place to start your cruising.
Glad to see you currently sailing a 16' boat - the life you described doesn't lend itself to maintaining a big one, and you gain seat-of-the-pants feel for sailing that you can't get from a big boat, like moving from a dirt bike to a Harley. Folks who start with a 36' or larger face a steep -- and often expensive -- learning
curve, and are a source of both consternation and amusement for the rest of us.