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Coming up the ICW from Canaveral to St. Augustine is a long two day run. No problems with 6' draft or 55' mast so long as you watch your depth gague. You will find some bridges that open only on schedule and some on demand so a cruising guide will help greatly.
As for coming into St. Augustine from the water, I went out and back in on 6/28/09 and never saw anything less than 12' in the channel at low tide. You MUST start at the Sea Bouy (the only charted bouy near the St. Augustine inlet) and then follow the channel bouys in on visual. It can be a slow ride in if you are fighting an outgoing tide. It can be a slow and rough ride in if you are fighting an outgoing tide and an onshore breeze.
Good Luck
--Eric
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