Relaxing?
What route do you take and how much time (days) do you give yourself?
Coming from NYC, you have both NJ and DC to contend with.
We drove down from just outside of Philadelphia two years ago for a cruise. 95 is a white knuckle drive almost the whole way down. I booked a return on the Autotrain before our cruise departed
Thinking that maybe I timed the traffic wrong (didn't leave early enough?), we did a similar trip over the holidays this last December (down to Charleston SC to spend a couple nights, and then on to parents/grandparents in Sarasota)... basically the same experience... 95 is a nightmare IMO.
My advice to others thinking about driving down... unless you have a large group, extra vacation days to spare, and/or in your 20's... I really don't think it's worth the safety risk and added stress to drive.
Driving
at WDW is relaxing. But the drive down doesn't bother me at all.
We leave NY at around 4am on a Saturday so the NJ Turnpike is empty and the DC corridor is really not congested by the time we get down there. I use Waze for routing, but it's basically 95 the entire way. I set the cruise control at 70 and stay in the middle or right lane depending on how fast everyone else is driving. Southbound, Waze always sends us 895 through the Baltimore Harbor Tunnel and then 295 (Baltimore-Washington Parkway) and 395 through DC back to 95. We use the 395/95 express lanes in VA. Coming home, we get through DC early evening on a Saturday and there's not much going on in DC at that time.
The first two years we stopped over in Santee, SC on the way down. Last year we stopped in Savannah, GA and are doing the same this year. The return trip we have always just done straight through. My wife and I (both early 40s) split the driving and our kids (triplets, nearly 11) are pretty good in the car. At some point I assume we'll stop doing this, but it really beats spending around $2500 to fly 5 people non-stop from NYC to MCO and back. Our trips are normally 2 weeks, and we also like to rent a car, so it eliminates that expense as well.