We have made the drive twice - we live in WV about 30 minutes from the PA Line about and hour 1/2 south of Pittsburgh.
Our first three trips to WDW we flew - but we decided we wanted to drive to see what we were missing on the highway.
So last December (2009) we had a 3 night cruise booked followed by a week at WDW. SO - we decided to book on property at BLT for one night before our cruise to assure we were in closer proximity to the port a day before we had to be.
Our cruise left on Thursday, so we decided to leave home very early Tuesday morning.
We got home from work on Monday - didn't want to dirty the dishes so we went out to eat. During dinner I said - "What if we left tonight and just stop when we get tired to get a hotel so we get on property sooner - and might even get to go to a park?" My wife who isn't a fan of spontaneous decisions said - "For once I am going to say whatever - as long as you know we can get a hotel for the night." Of course I said we could! HAHA
We left dinner - went home - packed the car - and got out of town around 10:30 - 11:00pm
We drove all night - stopped a few times for restroom breaks - slept for 1/2 hour at a rest area - and slept for an hour or so around 5:00am - then woke up and continued driving. Around 7:00am we realized that we WERE going to make it on property that day. SO we said what should we do?
We are DVC members - so we called Member Services and sure enough - a Studio was available for one night - at our absolutely FAVORITE resort - Wilderness Lodge.
We literally rolled up to Wilderness Lodge as the clock changed from 3:59 to 4:00pm - SO we went in - AND our room was ready! YIPEE We just added an extra day to our vacation!!!!
So we got into our room - which was an amazing ground floor room with a beautiful wood meadow view with bunnies and squirrels - we showered and said what now - so we went out to pick up a few last minute things - went to dinner and then made our way back to the room to get a good night's rest.
The next morning we slept in - got things packed up to move to Bay Lake Tower. We had the dining plan for that one night with a reservation at Ohana so we spent the day at the Magic Kingdom and then went back to BLT in time to enjoy the fireworks from the Top Of The World Lounge - and THEN to dinner - we made it back to our room around 10:30 or so and really started to get into cruise mode!
I would HIGHLY suggest leaving as soon as possible - driving through the night - and leaving your schedule open for ... whatever!
One variable that we did not have to worry about - kids - we don't have any (yet!)
If you have a reservation and it turns out you could have driven further - or possibly even made it all the way - you will just lie in bed thinking of ALL the fun and good times that await you at WDW!!!
On our 2nd drive things were different because I had recently reconnected with my god parents - and wanted to spend a few hours with them - so we drove to Charlotte, NC - making in in shortly after midnight - and then left the next day around Noon - making it to WDW by around 7:00pm if I remember correctly.
I travel a lot for work - so I have hotel reward points to use - so all I have to do to get a room on the road is call the rewards program hotline and tell them where I am - what I am looking for and how long I want to stay.
I am not guaranteed a room (unless I book 48 hours in advance) but if our schedule is totally flexible - it doesn't matter where we sleep.
We have stayed in Columbia, SC, Charlotte, NC, and Jonesville, NC.
As we are usually traveling on weekends - we always find someplace to go to Mass (we are Catholic) - and we have had some really great experiences doing that! We've really seen some beautiful Christian communities that really made us feel welcome. We also enjoy visiting the Basilica of the Shrine of Mary Queen of the Universe when we are at WDW. Such a cool experience to worship with a congregation of folks literally from every corner of the globe.
But anyway - as I always say - have a great solid plan.... to be FLEXIBLE!
While yes, we have been lucky in always finding a room where we needed one - we have also always been flexible enough to do what we had to do.
If you are traveling with young ones - it may be a good idea to think of a few scenarios, and make more than one hotel reservation (being sure to check the hotel's cancellation policy) The hotel chain I stay with when traveling for work has an almost across the board cancel before 6:00pm with no penalty which I think is really great as it allows me to be flexible and maintain a schedule and make a decision after I finish up a day's work about where I'll spend the night.
In the end - pack a pillow - be prepared for an exciting drive - and bring along at least 1 extra book!