Re: Sailing across the Florida keys
" I would go to Key West and around."
Even better if you can check out the cruise ship schedule for KW and get there on a day when 5000 of your new best friends aren't also going to be visiting.
Hurricane season, good weathercasting, flexible schedule, and a couple of ICW guides and charts with a red highlighter to mark off where you don't want to go. Parts of that trip will have to be offshore and that time of year, you'll need to know where and when you can or can't duck in if you need to.