Well, let me offer some thoughts that may help.
I will not fly. Period. I have flown before and loved it. I flew from my home here in Georgia to California 3 times over a period of 4 weeks one time. It was exhilerating and never boring.
Now then - DON'T READ THIS PARAGRAPH UNLESS YOU WANT TO GET A LITTLE WIERDED OUT. (So, you're gonna read it anyway, huh?

) We did have a flight coming from either LAX to Dallas-Fort Worth, or Dallas to Atlanta that seemed very tense. I believe it was from Dallas to Atlanta because I think it was the last flight I was on. Anyway, for some reason, it was very uncomfortable. I knew we were running late, and the pilots were trying to make up time, apparently. Everyone on the plane was very quiet. I don't know why, but it was just one of thse thing you could sense. Anyway, when we came in for a landing, I noticed that the things we were passing on the ground were usually things that I thought, at least, I would normally see going past after we had landed. When we did touch down, it was very hard and a lot of people on the plane screamed out, just for a second. Then, we passed all of these fire trucks and ambulances that had their lights on and were waiting as we passed. That unnerved me and I think a lot of people on the plane. The stewardesses came over the loudspeaker and said that it was just a drill and that we shouldn't worry about the vehicles that looked as though they had started following our plane. When we stopped, there was a sigh of relief. But, there was nothing out of the ordinary as far as de-planing, so I'm not sure what the deal was.
OK...BACK TO THE NON-SCARY STUFF.
Actually, plane travel is really safe. The only reason I flew to California is because of a girl. As a matter of fact, I always told myself that a girl would be the ONLY thing that would ever get me on a plane. Now, I'm think maybe a trip to Orlando would be good reason, also.
For you, the first alternative I thought of was Amtrak. I looked on their site and a ticket would run you about $118, each way I believe, per adult. I put in from Cleveland to Orlando, and unfortunetly, Amtrak still hasn't figured out how to get someone from point A to point B without going around the world. You'd have to go through Washington and possibly NY to get there and back. Pretty ridiculous. The trip would also take about 27 to 30 hours. If you had a sleeper cabin, then that would be kind of fun. But, I have another story about Amtrak, in case you aren't familiar with it.
I took a train earlier this year from Atlanta to New London, Connecticut and the trip took about 22 hours. I thought of all the cool stuff about trains. Disney World has great trains. It's very nostalgic. I had this vision of riding through the old west on an Amtrak train. (I'm from Georgia, remember, so I may not be the brightest bulb in the pack.) Anyway, it turns out that modern trains are like Greyhound buses on rails. They're not a bad way to travel, though, and I would take one again. However, I wouldn't take a long trip without renting a bedroom. That would've changed my whole experience. Instead, I was stuck trying to sleep in a seat like you'd find on a GReyhound. It was comfortable, but not for 22 hours. The nice thing is that you can get up and walk around and stretch your legs and even have breakfast, lunch, and dinner in the dining car. There's also a snack car for when you get hungry, too. It looks like it would take you about an extra 10 hours, something you're probably not willing to do, to take the train rather than drive. I even had a friend that went from NY to Miami on Amtrak and he loved it because he had a sleeper cabin and they even hauled his car along. Sounds like that part may be $$$$. But, all in all, a train would be nice if you had the time and had a bedroom.
So, the question would be: How much time do you have on your vacation? If you plan to drive, then I would try to break the trip up, if possible. I drove to Dallas from my house and it took 14 hours. I ended up staying over somewhere. But, if you don't break the trip up into 2 days, you could drive it in 1. Make sure to take breaks when you need them. And, it seems like I have jet-lag the day after I drive anywhere that's a long distance.
OK, so I probably didn't help much. But, if nothing else, let me say this: Please don't force anybody to do what they don't want to. I know that wouldn't be your intention, but if they have a fear of it, maybe that's not all bad. And, (again this isn't something you would do, but I'll say it anyway) don't give them too hard a time if they're not comfortable with the idea of flying. The whole time I was flying to California, I kept thinking, "Only a girl could get me into something like this." And, maybe Disney...
Good luck to you!
- John