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Cruising NY to Florida -- intercoastal
As you can see, everyone has their own opinion. Big versus small, full keel versus fin keel, deck stepped versus keel stepped. I bought the perfect boat FOR ME, the right charts FOR ME, and went down the ICW sometimes and outside sometimes. I would talk to as many (experienced) people as you can find, take everything they say with a grain of salt (including my opinions), and after a while, you will befriend and trust those who do things (right or wrong) the way you think they should be done. After a trip down the ICW, you will have your own opinions, and think like the rest of us, that everyone else is doing it wrong and you are the only one with his head screwed on right.
I am too much of a coward to go down the ICW without charts, so I bought a good chart book, a good companion book, and asked those I trusted to mark down their favorite anchorages. If you draw more than 6'', you will want to sail outside more than if you draw less than 6''. Everyone occasionally runs aground on the ICW, and I have never seen anyone go to the extremes of getting unstuck like you see in the sailing magazines (filling the dinghy with water while suspended from the boom, kedging off with another anchor, etc.) The first time it happens you will think the world is ending, the 10th time you will swear, hit reverse, and either back off the mud or wait an hour or two for the tide to come in.
The experience will come - the most important thing is to JUST GO!