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Any reason you wouldn't just bring it around by water?
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Yes, a few reasons.
1. My boat is VERY slow. If we take it by water we will plan a 3 day trip going as far as Cape May on day 1, Atlantic City on day 2, and to the marina on day 3. As I am self employed it's difficult for me to be out of touch for 3 entire days. I'll be stopping the entire trip to answer e-mails on my blackberry dragging the trip out for 3 weeks!!

I will make a trip like that someday but now is not the time.
2. I've been having an overheating problem (see my other thread). I am afraid I might experience a mechanical problem in an unfamiliar area.
3. From what I see talking to one transport company I will save almost half having the boat transported vs. burning gas to drive.
It would be a great trip but just not feasable right now.