First, I'd suggest buying a book called a "Passporter" it's written by Jennifer and Dave Marx and it's my favorite planning book. Others will likely weigh in on their planning book, but this is my favorite since it has pockets where I can store everything and I think it is very well organized.
I agree with the previous poster -- deciding when you want to go is the first step! While "value" season is certainly the cheapest...my family wants to go to Florida for sunshine and warm weather...temps in the 60s just aren't warm enough for my family to swim and that's one of the BIG things on my son's list.
I personally like to go AFTER the spring break crush...but before the Summer rush -- mid-April (depending on when Easter falls) to just before Memorial Day is good...not too hot...not too cold...just right!
As far as money saving tips...don't fall into that trap of "off-property is cheaper than on-property." The value resorts are themed really well for kids (my son loves Pop Century for that reason...even over the Grand Floridian!) and are very affordable. Last year, we actually purchased an annual pass (yep, we don't live anywhere NEAR Orlando) and got a $52 per night rate for Pop Century in early May.
Some people love the dining plan. It does have some advantages, but they largely depend on how your family likes to eat. We have never done the dining plan and I don't think we will (unless maybe it's free again like it was this fall). It does give you the benefit of "pre-paying" for all your meals, which some people really like because of the budgeting aspect of it. We generally eat breakfast in our room (cereal, cereal bars, etc) because I'm just not a bacon and eggs kind of person (cold pizza, sure...but eggs?) and my son and hubby like cereal a lot. Lunch, we might do a sit down place (they are cheaper then) or we might eat at a counter-service place and then have a nice dinner somewhere (again...you'll get lots of opinions on restaurants on the DisBoards). We're not big snackers and we generally bring bottles of water to the parks with us (I just can't handle paying more than $.99 for a large bottle of water!).
As far as tickets go...definitely go to mousesavers and sign up for their newsletter. You'll get an e-mail with a special savings for tickets. I've done it 3 ways: 1) bought the package from Disney with room and tickets; 2) booked the room with Disney and bought tickets from a discount broker and 3) got an annual pass. It depends on how long you are going (and what the room discount is for annual passholders) as to what the best thing is for you. If you want the dining package, then you'll need to book everything through Disney. By the way, if you are a
AAA member, you can generally get a bit of a room discount either from AAA or Disney. If you don't want the dining package, then either a ticket broker or an annual pass might be the way to go (use the annual pass calculator to see if it's worth it for you). The one downfall with the Annual Pass is that you get these really cool mailings from Disney with incredible hotel rates that make you want to book another trip (take us...we went in December of last year, May of this year and we're going again over Thanksgiving...just because of how "cheap" it is to go once your tickets are all paid for!).
If you have questions or need help, let me know. You can send me a PM (private message) through the Boards and I'll be happy to help.
Last thought....here's what you CAN'T miss with your son.
1. Riding up front with the driver on the Monorail
2. Taking a tour -- we loved the Family Magic Tour of Magic Kingdom and my son loved the Pirate Tour from the Grand Floridian (it gave me some down time too which was great!) My husband loved the Segway tour of Future World at EPCOT! At Thanksgiving we're doing Mickey's Magical Milestones tour.
3. Riding the bus back to your resort with a great bus driver -- some of them ask trivia questions and crack jokes that are wonderful after a full day in the parks!
4. The
Lego store...'nuf said...all legos!
5. The "Stars and Cars Motor Parade" at MGM...my son's favorite (as he puts it...it's not all about some dumb princess)!
6. The street performers at Animal Kingdom (and really everywhere)...take a few minutes as you are running (from ride to ride to show) to enjoy these stops...they are great!
Have a TON of fun...it's the best place for being a kid with your kid!
Karen