T.,
The size of your family makes a difference. For your size family, I would recommend staying onsite. You get free transportation to and from the airport and the parks and that saves a bundle. The value resorts in the offseason go between $62-82 per night and you won't do much better than that offsite even without the free transportation.
The age of your children makes a difference, too. Age 10 is an adult in Disney's eyes and you will pay more for food and admittance, so you may want to go before your son turns 10.
We went the end of Jan/beginning of Feb and I would highly recommend that time frame. Disney is next to deserted. It was unusual to stand in line for anything. It is 60-70 degrees. I have been with college roommates in June and it is HOT and HUMID and we spent more time standing in line than anything else.
September is a great time if you are willing to take a little risk. Yes, it is hot and humid and hurricane season. But Disney almost never shuts down (maybe 1 day per decade) and it is the only chance at getting free Disney Dining package. If you have to pay for the dining package, it is $41 per day adults and $11 per day for kids. It is also lowest attendance month of the year.
I would recommend staying on site if you have no more than 2 children + baby. When you look at the cost of car rental and parking, it is cheaper to stay on site and take advantage of the free transportation. We stayed at the Pop Century Value Resort and really enjoyed it. It is like a 3 star hotel in Disney decor - nothing spectacular, but we were only there to sleep. It is at the lowest end of the Disney on site resorts (we paid $62 a night) but all the Disney benefits are there and the room was clean and all we needed. If you go up in price ($160-$1000+,) you get more hotel restaurant choices, better views & fancier grounds, more pools to choose from, and more transportation options to the park. (Buses every 15 minutes vs. buses and boats or trams.) My only complaint about Pop Century was that the bus stop was the furthest from the park. The more you pay the closer bus stop you get. But I guess that is fair, isn't it?
Buying tickets: I recommend at least 4 days in order to see a good overview of all 4 parks. Disney charges through the nose for the first 3 days of tickets, after that, they are nearly free - $1-3 per person per day to get in. It is to their advantage because after the third day statistically people start shopping and spending money and don't do as many attractions. Your airfare will be the same regardless, so you may just want to stay longer, especially if you can get free meals, too.
- You can upgrade to "park hopper" (visit more than one park in a day) and sometimes you can get this for free. If you can’t, I would just plan to see one park per day. If you get park hopper free, I would spend ½ day at Epcot and more time at the Magic Kingdom.
- You can upgrade to include water parks for a couple hundred dollars, but they are geared for older kids who can handle fast waterslides. There is stuff to do for little kids if they give you the upgrade for free, but I wouldn't pay for it because your hotel will have a heated pool open year round that your kids may like just as much. It’s cheaper to just take your kids to a local water park for the day. Sometimes you can get water parks in your package for free.
Small World Vacations Travel Agency is great for getting you a good deal. Saved us an extra $300 + free park hopper & water park after I searched deals for 6 months.
www.allearsnet.com and www.mousesavers.com has great info.
If you stay onsite, Disney will give you free bus transportation to and from the airport and in between parks and hotels. If you use Disney’s free airport transportation, pack so that you don't need your checked luggage for several hours - they may not come to your room for 2-4 hours or more because Disney gets your checked bags for you. But now most airlines charge $15 each way per bag, so it may be better just to carry on smaller luggage.
Because of the dining package, we did some character meals - WAY FUN! We had the best time at the Liberty Tree Tavern in Magic Kingdom. The rotating restaurant and the underwater restaurant and the princess character breakfast are the best in Epcot. We did Cinderella's castle (last meal before they doubled the prices / voucher points) and it was a bit of a disappointment. You could tell that Cinderella & Godmother were a bit burned out from all the brats they had to deal with. Hopefully they rotated their cast members and brought in new ones. We didn't do any other character stuff, the meals were plenty and saved time for other things.
Where to eat: If you can go between late August and early October, I would highly recommend getting the free dining package. It comes with staying onsite and each family member gets 1 fast food meal with drink and dessert, 1 restaurant meal with drink and dessert and 1 snack per day of your visit. Disney offers huge meals and any but the “all you can eat family style” character meals can be split. We didn’t need to purchase any additional food while we were there. We did attend some character meals and had a blast. Liberty Tree in Magic Kingdom and Coral Reef at Epcot were the best. If you can’t go in the fall and have to pay to eat, fast food meals are about $9-11 for adults and $5-8 for kids. You can still split. Cosmic Ray’s in Magic Kingdom and Sunshine Seasons in Epcot give you ½ an entire chicken plus two generous side dishes for $9. That can be enough for 2 people. You can also bring in food you pack as long as it’s not in glass containers or in a big cooler. (And no straws in the Animal Kingdom, including juice box straws.) Character meals are $30 and up for adults and $10 and up for kids, so get the dining package if you want to do those. Paying for the dining package costs $40 for adults and $11 for kids per day.
As far as shows, parades and fireworks go, you can't go wrong. They are all really good. I would highly recommend Storytime with Belle. Hardly anyone knows or goes. It is surrounded by trees - quiet and secluded and a good break from the Disney chaos. Belle tells the Beauty and the Beast story and invites kids to come on stage, dress up and do the parts. It was wonderful! The only things I wouldn't recommend attending are Ariel's Grotto and Stitch's Great Escape - I'm not sure if they are even still there, but our only disappointments the whole week.
I wish we would have brought rain ponchos like everyone says to. We got caught in a bad pour. If you are trying to pinch pennies, go to the Disney Store, Target, Walmark or eBay and prepurchase souveniers to bring along. We had all sorts of Disney trinkets and new Disney PJs for our kids - paid a couple bucks on clearance and the kids were thrilled. We also brought our own glow sticks for the parades. I bought brand new autograph books on eBay for $5 including shipping - they are $16-20 at the park. We had matching Disney outfits for the kids everyday. It was fun, they were easier to keep track of, and we were able to overcome the temptation of buying $28 t-shirts for them in the park. They wore those outfits at home afterward until they literally fell apart. You could also get Disney t-shirts ahead of time for a few bucks.
www.kayak.com might get you the best airfare. I have seen flights from MSP to Orlando for $169. We used AA.com because we had saved up point for two free tickets, then used their "travel deals alert" on the website to know when to purchase. www.farecast.com is a good predictor, too.
Use fast pass. Fast pass is a ticket to come back and ride later without having to wait in line. You will see this for popular rides and busy days.
My last bit of advice is to RELAX and ENJOY YOURSELF. If you are anything like me, there is a temptation to do it all, see it all and get your money's worth. That can ruin a Disney Vacation, especially with little kids. We did 4 days at the parks and got to see a lot, but not all of it. Just get in what you can.
You can go to the Disney website www.disney.go.com and see attractions and order a free DVD that's a lot of fun to watch before you go. It comes with a very helpful map.
If you have any other questions, feel free to email me.
Have fun,
S.