I'd be really interested to know what experiences other boaters have had along the Intracoastal Waterway as far as holding, and places to wait out a blow, places to avoid.
My boat is an extremely heavily constructed fiberglass schooner of 33' on deck, 12' beam, 5' draft, with 8600 lbs of internal lead ballast. Displacement is 24,000 lbs and the fiberglass hull is 1 1/2" thick at the keel, 1 1/4" at the waterline, and 3/4" at the sheer. It is solid and sound, and you can see how hard it would be to raise if I'm dumb enough to let it get sunk. Like any other boat, if you fill it with water, it sinks. It's just a little harder to fill than most.
I plan to head away from the Tampa area this year and go through the Okeechobee and work my way north to the Chesapeake. If I get a good weather window, I might sail around the Keys instead, but if there's no wind, I'll motor through the shortcut.