I have pulled many smaller boats all those routes over the years.
If you take I 81 to I 77 to I-26 to I 95, in essence you avoide the major headaches to include NYC, tolls, Baltimore/washington, I 95 thru parts of Pennsylvania near Philly and so forth. The trip is breath taking and in Virginia if you are a Civil War Buff, you can stop off in Winchester old town, New Market, Lexington (VMI & WL) and you avoid all the crazyiness. In fact, near Roanoke is a restaurant called the HOme Place and it is good food and good pricing. I own a dodge caravan and I have pulled heavier boats with it on that route.
If you want to go I -95 and want to avoid Washington/Baltimore, then pick up 301 south just past the Delaware Bridge of I-95 and take it to Rt 50 west. About 15 miles west of Annapolis take 301 south. Watch out for the cameras in several locations. Once in VA on 301, follow the sign to I-95 and take I-295 around Richmond going toward Rocky Mount, NC. Then I-95 south taking I-295 around Jacksonville, Fl during rush hour traffic.
If you go I 95 thru Virginia, do not speed particualry at the VA NC border as Emporia is known for giving out safety speed awards.
Crazy Dave Condon