Some of my points have already been echoed by everyone else....
1) Leave early in the morning, and i don't mean 6am, i mean 2-3am. Definately use a radar detector if you plan to cruise at a good clip. Leaving this early will put you in the NYC/NJ area by the early part of rush hour but if you follow point 2's advice, you'll avoid it. It will also put you at the DC Beltway around noon-2pm when you'll avoid all the DC rush hour. The Beltway is one of the top 10 bottlenecks in the country and you DON'T want to get stuck there, especially after 10-12 hours of driving already.
2) When you get to the end of CT, you have the option of taking the Cross-Bronx Expressway(staying on 95 essentially), or taking a right up and thru westchester county and over the Tappanzee bridge, down-Hudson from Westpoint. I'd suggest doing the Tappanzee. A handful of miles after you cross the tappanzee is the southern exit onto the garden state parkway. If you were to stay on 95, aesthetically you'd be depressed. White Plains itself isn't anything to look at(highway-wise) but the tappanzee and then the garden state parkway stretch are ALL GREEN and i've rarely encountered backups around this area, sans rush hour travelling which is horrid anywhere near NYC. The Garden State Parkway eventually merges with the NJ Turnpike via marked exits but you'll have cut out the worst chunk of it up near NYC.
3) As some have said, if you aren't used to distance driving and/or are showing signs of fatigue, then anywhere in VA is a good place to catch some sleep. I'd recommend doing searches on mapquest or some of the better chain's sites and write down info on a bunch instead of just one. I usually pick a state or two i figure we'll stay over in and write down a bunch at various exits because we never know exactly when we'll want to stop driving. If you book a hotel ahead of time you may find that you could/would have driven longer and made the 2nd day's driving that much less. Since its your first time i'd say, like the others, that VA is probably a safe place to focus on for that first night.
4) If you've never driven through the south then be prepared for "the wall," as an ex-gf used to call it. New England, and even the tri-state area are no comparison to the size of the southern states and how long it takes to get through them. So if you aren't used to it, your first time doing this drive is going to seem like you'll never reach south carolina, and then georgia, and finally florida.
5) "South of the Border" and other "attractions" are advertised constantly on billboards in the carolinas depending on whether you're headed north or south. Its one of those things you'll stop and see and i'll leave it at that...:lookaround:
6) Once you get through South Carolina you start to get excited because you're only in Georgia briefly and then you're headed towards Jacksonville. The Jacksonville interchanges are interesting to say the least. After that its all straight forward; 95S to I-4W.
7) One last thing is depending on what time you're hitting the Orlando area, you may want to take the Greenway(that's the name, orlando locals, right?) which is a tollroad that goes around downtown orlando and right to the WDW vicinity.
8) For your drive back, if you can make it back to mid-NC/S. VA you'll be in good shape. Just keep in mind starting out that 2nd day to avoid NYC traffic and take the Garden State->Tappanzee-> White Plains->95 again.
Lastly, a month or so before your trip, look up construction adviseries for the 95 route so that you can possibly flank it to keep on schedule.
Good luck!
:wave: