Hummmmmm..........I'm not sure what I would do if I were you. Only you really know your child, but.........
I have flown with a 16 month old and I have driven from NY with a 20 month old...............I would so much rather drive and I have a longer trip than you do.

But that's just us.
We have flown so many times......to San Diego, Orlando.......and we have driven to Myrtle Beach and Orando about four or five times now. I just don't like that I can't take everything that I want on a plane, but yet it seems like I'm taking the house when you have to carry it all through the airport.

The car seat, the stoller, checking the stroller, connections (we live by a small airport so we always have a connection flight

), uptight because I think my kids are being too loud on the plane, feeling like sardines, ........and that was all before 9-11......now with more restrictions on what you can take on board and waiting times, I almost break out in hives thinking about it.
But I can understand you not wanting to drive if you don't have a child that is a good sleeper or doesn't like to travel. We are very fortunate in that way, I guess.
When my son was 20 months old we went to WDW. We broke up the trip and stayed overnight in a hotel. No problems, but he was a good sleeper even in the car.
Last year, when he was 4, we started out at 7pm. The kids were awake for a little while and then it was bed time and they slept all night until 8am when we stopped for breakfast. We got into Orlando around 2-3pm, checked in and took a little nap. DH and I both decided we would do this again. We have a conversion van so we have tons of space, we stop whenever we want to at rest stops or a for a "pretty sight", we also stop for a meal or two that is sit down and we take our time. But because we drove at night, we only had about 10 hours of them being awake. And believe me, I needed the break from my 11 and 8 yr. old DD's as much as I did the 4 yr.old.
But like I said, only you know your child. this is just what worked for us.
