1. You have a lot of time in the Turks to Georgetown section of your routing...that piece took us 3 days so unless you are stopping to smell the roses...you can save time there. From Georgetown to Nassau can also easily be done in 3 days.
2. Crossing to Jacksonville directly is not a problem and you will have help from the stream...BUT you should have charts and bail out alternatives if the weather threatens to kick up. Ft. Pierce, Canaveral & St. Augustine are all good inlet alternatives.
3. As to storage...one of the safest places down south statistically is right past Jacksonville on up the St John's River up in GreenCove Springs which is as far as you can go with your mast. Another alternative in Georgia is Brunswick but they get full quickly and you should call to reserve. I don't consider anywhere else in GA/SC or NC hurricane safe for an unattended boat. Up the Chesapeake is much safer but still no absolute assurance as I tended to my boat during 3 such hurricanes over a 20 year period there.
4.With no insurance on an expensive boat...I'd be inclined to bury her as far up the Chessie as possible. Since you can't afford insurance...I assume you can't afford to lose her either.
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