Hey Jocie! Welcome, I am also a new member (just under a month) and found this spot to be extremely helpful in planning/preparing for a trip.
On a side note, I'm born and raised in Toronto (Mississauga is where I now reside with my Husband and 2 sons) but have many relatives (father's side) in Winnipeg and Portage la Prairie!
We did the trip from Toronto 2 years ago and are planning on driving again next summer. We took I75 the entire route and there is a wonderful book - sorry can't remember the author - that I picked up at Chapters on I75. The author lists every exit and what is available at that exit - food, gas, hotel. Also it had mileage down the side of page and tons of coupons and interesting facts on the area you are driving thru. I found this extremely helpful when deciding where to stop for lunch, how many more miles it would be and making sure the restaurant was a Cracker Barrel. I made the mistake of stopping at one on our first day in Ohio. I had eaten their before on business trips to the States but my boys had not. Once they tasted the food it was Cracker Barrel for the entire trip down and back. Anyway sorry, I'm getting off topic.
At the time my boys were 13 and 9 so I made sure they each took a knapsack with handheld games, crossword puzzles, reading books and CD players with CD's. Our van does not have a DVD so they had to settle for music. I also packed a cooler bag with water, juice, granola bars and Doritos. They also brought their own pillows from home and make sure to take wet wipes for hands and face.
I gave each of them a map with our route highlighted in yellow so they were able to follow along and not continually ask for my map.
We made sure we stopped every 2 hours for a 'pee' break and a quick stretch. I 75 has rest stops every 50 miles and they were clean and tidy (except Ohio they had to be the worst on the entire trip). They also had machines to dispense cold drinks and snacks and some even had small cafeterias for fresh coffee.
The trip from Toronto is approximately 24 hours. We decide to do it in 2 1/2 days. On the 2nd day we stayed just inside the Georgia border. The next morning we slept in, had breakfast and then travelled 30 miles down the road to the Florida border. This was the most important border crossing and we had to stop and have our picture taken under the Florida sign. We then drove another 4 hours into Orlando and shopped until our room was ready. I didn't want to drive too many hours the last day and it worked well for us. Once we arrived at our htl. we were able to unpack, relax, swim and have an early night so that we would be rested and refreshed for our next day visit to the Magic Kingdom.
Next year will be more challenging I'm afraid. I am looking into purchasing those personal DVD players (1 or maybe 2 if I can get a reasonable price) so they can bring along their favorite movies. Seems they need more to do as they get older so this may help a bit. Also we added a little black toy poodle to our family last summer and I have been told that if she does not come on our family vacation then they may boycot the entire thing so I now have to find hotels that allow dogs.
Anyway have a wonderful time browsing the boards, there are also several ready good sites that offer tips on travelling, packing, and what to see and do in WDW.
