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Just as a reference I brought my 34 Sabre from Annapolis to St Pete Fl leaving End of October and took 32 days. We had several 2 day stops for weather but generally were pushing pretty hard. We anchored or got slips every night except one.

ICW all the way to Hilton head then outside direct to Fernandino beach. You should figure a max of 50 mi / day and always plan out your next day including stopping point the day before.

Good luck, its a fun trip that you can do with a friend and enjoy.
 
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