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On the ICW you stop every night and anchor, so it's not a continuous trip, in the sense of trying to stay awake for long periods of time. There are many good anchorages to choose from along the way. (Get a copy of Skipper Bob's "anchorages along the ICW" for help with that). When we sailed the ICW, we planned on traveling 30-60 miles each day.
Insurance companies look at the overall # of years you have been boating, what boats you have owned previously, and what boats you have operated (and where), including crewing for friends and charters. So if you're light on experience, you might offer to volunteer as crew for an owner looking for crew, especially multiple day delivery trips. Keep a log of all your time on the water and turn that in when you're to apply for insurance. In addition to helping you with qualifying for insurance, you should learn invaluable lessons from the the captains you sail with. "Crew listings" sections can be found on 7-knots, SSCA, and your very own Cruisers Forum.
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