I have made the trip around the southern end of Florida and it is very simple and enjoyable.
First I took the ICW south to Ft Lauderdale where I went outside and reentered at Miami. I highly recommend you stop in Bocca Chita for the night in Biscayne Bay.
We went inside all the way down to Islamarada where we satayed for a while (a year!). We very highly recomment BlueWaters Marina on the ocean side of Tavernier.
We crossed from the ocean side at Snake Creek and had an easy run up to Little Shark River which was well marked. Apparently we went during crab season and I have never seen more crab pots which are a real pain. It is worse than Maine and they are all in the channel!
From there we went to Naples and then Ft. Myers Beach which have numerous slip or mooring opportunities.
If you plan to travel north in Pine Island Sound, be sure to stop in Pelican Bay on the eastern shore of Cayo Costa.
'73 GB 42 CL #362
Punta Gorda, Florida