We are staying at Orange Lake Resort, so off site in a time share. We are driving down, so will have our car if needed but I think they may shuttle to WDW. Will check on that. I'm reading all I can. Thanks so much. I will check the calendar but I think it will be crowded no matter what as it is Memorial Day weekend and the week after. :/
Here's my thinking in a nutshell.
1. If you have never been to WDW, then you don't know. Don't beat yourself up over what you don't know. You don't know what attractions your family will love best, or which dining. MOST importantly, you don't know how long it takes to get from place to place!
Even though we have been to Disney a great many times, the last is almost always a fairly wide unknown (see below).
2. One BIG unknown is always the weather. Florida is essentially tropical, sudden downbursts are often short lived and (nearly) unpredictable, but common. Perfect weather = extras, bad weather can equal less. Then again, bad weather also= less crowds. May is close to ideal, except it might feel a bit hot. DO bring water tolerant footwear. I also strongly suggest buying cheap plastic ponchos, also rain jackets in case of longer rain.
The crowds will be worst very close to the holiday, and thin out further form that day/weekend.
3. I ONLY bring footwear that is good for walking. WDW is much walking. The day's fun often ends when your feet/legs hurt. I make sure everyone brings at least two pairs of quality footwear (alternate to avoid blisters!), where one is water tolerant! (Kali at AK, rainy days, to/from the pool) Walking shoes are worth every penny.
4. I go to Disney for the things that are unique to Disney. I can (fairly easily) visit thins like non-Disney water parks and mini-golf, and the Disney version usually costs extra.
5. Drink plenty of WATER!
6. With those basics, the rest is kind of icing. I wouldn't pick dining every day for many reasons. #1, it locks you down. I suggest keeping your first trip a flexible as possible, so you can accommodate the unexpected without any stress. Pick one or two options that sound very fun and are easy to locate.
7.You DO kind of need to pick your 3FP for each park day. No, we don't like this new system either. It helps to pick the # of park days you want, then which parks to visit. You'll probably want 2 days in MK, and one in each of the rest.
8. Simply put, any opportunity to zip when the masses zag, works in your favor. Avoid following the herd if you can do it happily. Pick the less crowded turnstile. Eat ice cream before lunch! You'll do very well if you simply choose to go on the older/less popular rides during the peak crowd hours (11am-4pm). The rides with FP, and the longest mid-day waits are the ones you want to ride outside peak hours or with a FP. Stretch as much as possible, but not to the point of misery.
9. Drink PLENTY of WATER! We carry bottled water. Disney's bottled water is $$. If you pick up one type of grocery item, buy water.
10. Did I mention LOTS of walking?!?!? Almost every WDW path is as long as possible! One of the best ways to prep for Disney is daily walks. Well, that and having a small emergency slush fund. We find most vacation problems can be solved with a little bit of $, and/or walking a little further.