We just took my son to Disney one of the weeks between Thanksgiving and Christmas. We avoided having to pay for an actual Disney ticket for him and most of his meals by going right before he turned 3. He had a blast! We stayed at the Disney All-Star resort. It's not physically at Disney but its just a short "Mickey Bus" (that what my son called them) ride to any of the parks (including the non-Disney affiliated parks). We stayed 9 days and did the parks 7 days. It worked out great we got to see everything we wanted. There are lots of places to have a beer, no place to gamble though. All in our trip (plane tickets, park tickets w/park hopper & fast passes, meal plan, park trinkets) cost us ~$5,500 going from Houston to Disney. My advice is to go during what they consider "off season" as it will be cheaper. Take your son right before his third birthday if it works out for you. Defiantly get a meal plan for you and your significant other you will save in the long run. Go through a travel agent they will help you get the best deals. Be prepared to be overwhelmed, all of you. Nap time is still a must so you don't have a super cranky child. Make sure to bring a stroller. Don't rent a car if you don't plan on going any where other than the parks its a waste of money, use their provided transportation. Don't over plan your park day's and be prepared to wait from some of the rides (fastpass really comes in handy). Fly into Orlando and take their bus. Bring a computer to upload pictures onto if you are using your phones or multiple memory cards. Remember to bring a few toys & the ipad or whatever to entertain the boy on the flight and in the room. Utilize the Disney Park app on your phone or tablet as the parks do have free wifi and some hidden phone charge stations. And apparently now make sure your son is vaccinated after hearing about what happened over in Disney Land recently. Thats all I can think of off the top of my head. Lastly have fun and relax.