re: Sailing across the Florida keys
Like others have said the ICW is not doable with your draft. You will have to be careful about Marathon Bridge because it is not the normal 66/68' height that most bridges are. You might have to wait until very low tide to get under it. I would go to Key West and around. Key West is way to much fun to miss if one hasn't been there before especially on a boat.
Catalina 445, Hull #90