Bob -
I tow from Herndon, VA (in northern VA 20 miles west of Wash, DC) to Key Biscayne, FL which is 1,067 miles by the most direct route. When I tow, I usually avoid the DC Beltway and I-95 north of Frederickburg, because it is a continuous traffic jam on that stretch of I-95 from the big interchange at the bottom of the beltway, all the way down I-95 to Fredericksburg. So, I swing to the west and take US 29 south out to Warrenton, VA. then US 17 south to Fredericksburg. This adds about 20-25 miles, but well worth it to me. All in all, it's about a 1,100 mile tow.
Once you reach central VA, the rest of the trip south is very easy driving.
I do it in two days, with one night over on the way down. I generally stay overnight in SC, and have a few hotels in mind that I know have good turn-aound room for trailers. Actually, in the Carolinas, most hotels just off the interstate have lots of room.
I actually enjoy the drive down. I usually go about 70 mph the entire way, and that is the speed limit for most of the trip. VA is 65, and most of the southern half of NC is 65. A couple pieces of GA and FL are 65, but the majority of the trip is 70. The trailer does fine at 70. Hubs are barelt warm when I check at rest stops. I bought an "overkill" trailer with the big 6 bolt hubs for this boat. The original trailer had barely enough capacity. The new one is not worked very hard. It's capacity far exceeds the boat's weight.
Assuming you have a decent trailer, you should definitely do the trip. You will not regret it. But, go down there enough to make it worthwhile. We took it down this month. we'll be down again in December with relatives joining us. We have our plane tickets for January and March. Then there's the return trip towing it north in April.
Another consideration is trailer storage, so you don't have to bring it back with you to NJ and you don't need to tow it down to FL again in the spring to pick up the boat. It's best if it is left there in FL to avoid dragging around an empty trailer. We store our trailer at the marina in Key Biscayne.
Let me know if you have more questions.