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DQOTD -- sailing southbound along the Florida coast

OK just doing some "what if" thinking about taking the boat south to Miami for the winter with the idea of hopping across to the Bahamas for vacation: Can't take extended time off so I'd probably break it up into multiple two-week segments, and leave the boat to fly back to "keep the plates spinning" at home.

In looking at the charts it's apparent the Stream comes very close inshore from Canaveral south, and there are shoals from near the edge of the Stream to shore.

What's the best strategy for getting the boat south along that coast, assuming late fall time-frame? (Would prefer to sail outside if conditions permit).

Also, what are some good places to winter a multihull in the Miami area (or other good jumping off spot)? Would prefer a fixed mooring rather than a dock (Yacht club reciprocal guest mooring also a possibility).

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