On the Bob trailer, you would have to talk to the ferry company. I have no clue. I carried my four panniers and handlebar bag on as carry-on luggage. I strapped two panniers together so that I had two "pairs" of panniers plus one handlebar bag.

I found that just about everywhere we went had good paving, so I see no reason that a bob would not work fine on this route. The route is quite flat, almost all the time I used only a few mid-range gears.

Bugs were bad at times in the campgrounds, bring repellent and be quick to put it on.

The guy I toured with grew up in North Carolina. He was always looking for good sea food. Be prepared (financially) to eat out occasionally.

You will find that camping, good food, most other things are more expensive than you would typically expect elsewhere.