Why is driving to Florida my favorite topic?
NYC to Orlando is listed as a 20 hour drive, but if you stay with the traffic and you encounter no accidents you may do it in less.
The half-way point is Fayetteville NC. No need to stop there, though, if you are starting at dawn. In 1974, we got as far as Savannah GA the first day, and that included a leisurely breakfast in the DC area, and the fact that I-95 was not completely finished!
Get one of those I-95 guides or go to the all-ears (sp?) site. (I differ with some of their details, but I will research before I challenge them.) Major motel chains cluster around I-95 at specific cities every 60 miles or so: Fayetteville, Lumberville, Florence SC, etc. South of the Border looks great but I have never tried their lodging or their food. Their gift shops are incredibly tasteless unless you like things like little potty scultures that include little people. (Not that there is anything wrong with them (!!!) but just where would you put them?) We would have enjoyed the very comprehensive fireworks shop except that it was absolutely forbidden to bring those things back into NYC.
My rule is the later you plan to stop, the fewer amenities you need. Our recent practice has been to leave at 4 PM on Friday, Presidents Weekend (!) and drive to Roanoke Rapids NC, arriving around midnight (or 2 AM if there has been snow in NYC. Snow has happened to us 3 times!) Snacks, no dinner. Big breakfast next morning. Motel 6 is a great place to arrive at 2 AM. You sleep, shower, and leave. If you want to hang around a pool or lobby, or relax in the room, definitely aim for a more expensive chain. This year we are leaving at 4 PM on a Friday in late April, but we are stopping somewhere around Richmond that night.
You MUST make a reservation (about a week ahead) if you plan to stop after 9 PM. Make a driving plan and stick with it! There is nothing more stressful and time wasting than the NO VACANCY sign at a late hour. You can not possibly know if there might be some gigantic NASCAR race in the immediate area that very weekend! It's a toll free call, and a deposit that you must cancel by 5 or 6 PM that night. Usually you know by then if you have come up with something better.
The only food available overnight is the stuff in the convenience stores attached to the overnight gas stations. Beware. If you really want dinner and plan to stop in a nationally recognized franchise, remember that they are not all 24/7 places. My favorite has been the TEXAS BBQ in Roanoake Rapids NC, and they even have a stuffed jackelope on display. (Somebody take the bait, please.) What I am saying is, stop to eat before 8 PM just to be sure. I wish I had info about good local places, but alas they are probably not near I-95 and they probably close even earlier.
Should you drive straight through? We once left at 4 AM and drove straight through to Ft. Lauderdale (3 additional hours) and got there about 2 AM. And then we slept most of the next day, so it was a wash. Motels are more expensive in Orlando. I would advise breaking the trip.
And I haven't mentioned the flat tire we had in Titusville, at 6 PM on Christmas Eve (another Ft. Lauderdale trip). This is the exact hour that everything closes on Dec. 24. Always expect the unexpected.
One driver? Even on the two-day plan, one driver usually needs more breaks than when you have a second person for a few hours relief. Minimal bathroom stops occur every 3-4 hours, hopefully timed to your gas stops. Get good mileage? You will have to stop anyway. Sorry.
Yes, we have flown. And then rented a car. (and enjoyed it.) Taxi/town car only once. But that's another topic.