We live in CT and made the drive down to WDW three times. If we had more time to vacation, we would not hesitate to do it again - especially since our two kids are now driving age and can pitch in with the driving. At the risk of repeating some of the sentiments already expressed by previous posters, I'll share some of the tips and lessons learned from these drives:
-We avoid Interstate 95 in the Northeast like the plague. It is a great drive once you get south of Virginia, but anywhere between CT and Washington D.C. is awful. Especially avoid going over the George Washington Bridge. We typically use an alternative route that takes us on Interstate 84W through NY and PA, then onto Interstate 81 in PA, then you head down in a southeasterly direction toward Virginia. There are a few different routes that will take you on this path. When you look at this on the map, it appears you are going very far West to go South, but believe me the time you save in NOT being stuck in traffic (and also the toll savings) is well worth it. Here is a route that I found on Mapquest that has the general idea:
https://www.mapquest.com/directions/list/2/us/ct/west-hartford/to/us/fl/orlando
-We typically stretched the drive over 2-3 days and stayed overnight either with family along the way, or stayed in a moderately priced hotel like Hampton Inn or Country Inn and Suites. These are great because they are usually very well maintained and breakfast is included in the price of the room. I scour the travel sites for deals on these hotels and have been able to get some very affordable rates.
-Bring plenty of stuff to keep your kids occupied, like movies they can watch or games they can play in the car. When our kids were younger, each one had an activity center type of thing that hung down from the front seats and folded down to make a "desk" surface that they could use to write, color or play with their toys. We also used a portable DVD player and brought along plenty of Disney movies to get them in the spirit (like they really needed any help for that!).
-Pack some snacks that are easy to eat - ones that kids can on their own and don't get too messy. Pack plenty of water and other beverages in a cooler so you are not stuck paying crazy inflated prices for drinks at the rest stops.
-Speaking of rest stops, give yourself plenty of time to make stops...although UNDER NO CIRCUMSTANCES SHOULD YOU WAKE UP KIDS WHEN THEY ARE SLEEPING to make a rest stop. Hoo boy did we learn that the hard way! The major highways have plenty of rest stop options - we have found that Love's Travel Stops and Petro Stopping Centers are clean, reliable and convenient. Chick-fil-A restaurants are also very clean and their service is exceptionally friendly. The state-run highway rest stops in Pennsylvania, Virginia and South Carolina are fantastic and I am actually jealous of them. Any CT residents on this board know exactly what I am talking about.
-If time is of the essence, avoid getting bogged down at a restaurant to eat a meal, unless that is something that you really want to do. We typically would just grab a quick lunch at McDonald's or Chick-fil-A (or eat a picnic lunch of what we packed for ourselves) and then get back on the road as soon as possible. We kept the nice, comfortable sit-down meal for when we would reach our driving destination for that day.
-Another rest stop tip: Try to find a place that has some kind of playground or other open recreational space for your kids to run around and get their ya-yas out. Some of the state rest stops do have playscapes, but also some restaurants like McDonald's and Chick-fil-A have them.
-You may not need to rent an RV for this trip. They are expensive to rent and you will pay a ton for gas. We made this drive in a Honda CR-V and it certainly did the trick for us. As I mentioned above, if you search the travel and hotel sites, you can find perfectly good and clean accommodations for a price that I am sure would be less than the daily cost of an RV. In addition to the ones I mentioned above. we have had good luck with Microtel, Holiday Inn Express and Hyatt Place. Just be sure to check the reviews because of course individual properties can be better than others.
-We used this guide book the first time we drove down and found it very helpful:
https://www.amazon.com/Drive-I-95-History-Trivia-Interstate/dp/1894979974
-We would limit the amount of driving done in a day to about 8 hours tops, with each driver taking 2 hour shifts.
-I am a history geek, so we used this as an opportunity to visit some historical sites like Civil War battlefields, and there are plenty of places of interest along the way if you are into that sort of thing.
-If you are driving on I-95, you will see lots of billboard advertising for South of the Border. This is a tourist trap, but it has become somewhat of an institution I guess. We have never gone there, but we do find the billboards to be rather amusing. They usually have some corny joke starting with "Pedro says..." We play a game that the first one in the car to spot a South of the Border billboard wins.
Good luck and enjoy the ride!