Just so I'm clear on your plan, you are in Lake Okeechobee and planning to
head south towards the Caribbean/Bahamas/Cuba?
First, east or west out of the Lake you will have a
current assist. But if you are heading south once you hit
salt water on the Atlantic coast you will be fighting the
Gulf Stream. If you hug the coast the northerly set is usually not as bad but I have seen it 2-3 kts north just a quarter mile off the beach around West Palm.
I would probably
head south down the
west coast of FL which would put you on course to the
Dry Tortugas if you like,
cruise the Keys and beyond then as you mention, returning up the
east coast of FL with a big boost from the Stream. Down side to that
route is you will be against the
wind from the
Dry Tortugas until about halfway up the Keys. Also a beat if you plan on the
Bahamas but then that would be the case from anywhere in FL.