Trailerable boat vs. Catalina 30
Don''t think that you need the big boat for traveling the Intracoastal. The other day I ran into a guy who was entering the Erie Canal sailing a 23'' boat on his way to Florida. If the layout works for you don''t worry so much about the length of the boat.
Having said all that, consider going with something big enough to have an inboard engine. It''s a really long day if there isn''t any wind and you have to listen to an outboard whine for any length of time.
Good luck and happy sailing.