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I have done that trip south and have parked my 32foot monohull in Savannah for a month before returning north. The bridges from Ft. Lauderdale and south will drive you crazy...I had 14 in one day, only a few on demand...that''s a good place to go outside.
In many cases it is actually longer to go outside that go ICW because of the very long inlet approaches...check the cruising guides.
Another option is to cut across Florida from Stuart to Ft. Myers via the Okeechobee Waterway, then work south in the Gulf to seven mile bridge and Marathon. Two issues: a railroad bridge makes the controlling mast height 49 feet, and a drought has dropped the level of the lake, so check with Army Engineers at Clewiston, 863-983-8101. Much of this is described in my book, "Sailing to Hemingway''s Cuba", Sheridan House, Oct. 2000.
Have a great time. Dave Schaefer, SV Dream Weaver
 
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