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I can only advise from Jacksonville, and south of that. I always leave just before a northern wind comes along. You can be looking at 25- 35 knots of wind. I also hug the shoreline, and make great time to Miami. Along the coast there are a half a dozen inlets for you to jump inside if you wish.
The ICW is fun once IMHO, because it is slow. Although there is lots of sightseeing along the way. What ever you choose. Be safe, and BEST WISHES along the way....i2f
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