Nervous/worried about trip planning?

Don't get me wrong, I'm excited about our trip, but I'm also nervous. I'm the one doing the planning. We are going May 23-28, 2010, staying at the Contemporary, 6 day passes, can't decide on waterparks and more or a one day waterpark pass.
Here's the problem .... there are lots of new things this trip, I'm worried I've made bad decisions. 1st, this will be my kids' first trip during a time other than September. We made one trip as a family and one trip with me and one child (with friends). All three trips were in September, taking them out of school. Now that they are getting older, I did not want to take them out of school. I picked this week in May because they are out of school, but it's the week before Memorial Day and I was hoping most people aren't out of school yet. I am so very nervous about the parks being so crowded that it ruins everyone's trip. They are so used to walking on rides and getting to repeat their favorite rides, that I'm not sure how they'll handle the crowds.
Also, my daughter wasn't so excited about this trip (she gave me a "been there, done that" response when I first told her about the trip. Seriously, I have NO IDEA where that child came from! :secret:), but "agreed" to it when I promised we could go to waterparks. I'm trying to plan the trip and I'm not sure when we will be able to fit in waterparks. I like hitting the big parks in the morning so they are less crowded. I guess we can hit the waterparks in the afternoon, but I can't decide if it's better to buy a single day pass or add waterparks and more to our park hoppers. Big sigh. Decisions, decisions.
Also, I've scheduled several ADRs. I know from our last family trip that my DH isn't happy if we are doing a least one sitdown meal a day. Well, so far, I haven't scheduled a meal on Sunday - the day we arrive. I know we have to eat that day, but I'm uncertain what park we will hit. It will be SWW, so we'll probably skip DHS. We will probably start at Epcot, but MK has really late EMH, not sure if we will make it that late or not. I hope that we can just walk in some place. I would hate to give Mr. Grouchy an excuse to be grouchy on the first day!
Lastly, we are staying at the Contemporary. I guess this is a good option. My DH wanted a Deluxe. I thought BW would be better, but he liked the looks of the Contemporary. Now, my daughter is upset about the pool. She wanted a better pool, but if we were planning on waterparks, I thought she could **** it up with a not so great pool at the hotel. I also picked Contemporary because we could walk to MK - because I'm not a fan of public transportation and I thought ever other park is easier to park and enter than MK.

Oh well, I know this is long and rambling. Sorry.:( I was just wondering if any other planners ever had big doubts about every single decision about their trip. I can't believe I'm so worried about this trip, but I can't get over it. I think my biggest concern is how we will handle it if it's miserably crowded. We really are spoiled going in September. I hope I don't regret scheduling the trip for this time.

You are not alone! I stress everytime I do a Disney trip and I have gone at least once a year for the past 20 years and I still stress everytime I go and I don't even have children! I'm always afraid that I won't get everything done that I want to get done and I tend to over analyze everything. Let me guess your daughter is a teenager. We had a similar experienc when we took my 16 year old niece. Don't worry about it too much, I've learned that it always works out and sometimes things end up better than you could ever imagine!

I don't know how old your daughter is, but I know that once my sister and I were teenagers we loved Disney even more because our parents allowed us to do the parks by ourselves at night for EMH's or while they went back at the pool during the day. We loved having the freedom to have our own vacation time and do exactly what we wanted to do for part of the trip. Not sure if you already do this but it was great for us (and I'm sure for my parents!).

Don't second guess yourself...daughter will be OK with the pool...she probably doesn't want to go on the 'slide' anyway...she can always take her towel and go down to the beach area...can't swim there, but can tan. You can eat at the food court at the Contemporary...it's pretty nice and you can order a lot of different food. If you want table service your first night, you need to book...unless you want to eat at one of the resorts, you may be able to get in...depending on how many people you have in your party...smart thing is to book and see how you feel, if you cancel, some lucky person will get lucky...just remember to cancel.
We were there the week after Memorial Day, and although it was a bit more crowded than in September (I go alot in September for free dining)...it really wasn't that bad...but I haven't been able to walk on anything in a long time...except very early AM or very late PM.
:pirate:

Whew..that's awhole lot of stressin! Don't worry though, we all feel some during the planning process. It's does take some planning to have a successful trip, but be careful not to plan so much that you can't enjoy yourself. I'm assuming your DD is a teenager, hence the blase' attitude, but don't worry. Even if she won't admit it, she'll feel differently once she's there..they all do! If she's old enough and you're comfortable w/it, allow her some solo time. As for you, make some time to relax and really enjoy yourself. It can be done, even @ WDW and you deserve it! :pixie:

You sound exactly like me! Mostly my family was so glad not to have to do the planning, they were quite content. I did make ONE terrible mistake...which turned into a true magical Disney story. We had a day off site in Universal, which I *thought* was to end with dinner at Cape May. It was all written down, but I wasn't feeling well, and forgot to bring my planner with me. The cab drops us off at Cape May - no Ressie. It's 15 minutes before the time we're supposed to be....wherever. I go to the concierge - my ressie that night was actually at O'hana. I'm so upset I'm nearly in tears and apologizing to my family. The concierge calls a cab, and puts us in it for free and sends us straight over to the Poly - we were there with time to spare!!

Thanks for the words of encouragement.
My DD is actually 9, going on 25 ... she wasn't as excited about Disney because she wants to go to NYC instead. She's interested in "checking" states visited off her list! Oh well.
Her last trip was 2007, her brother's trip was 2008 - so, once I reminded her that RRC was closed on her last trip (she loved it on her 2006 trip) and her brother had the chance to ride it 12 times one day (have to love Sept no lines!) and she missed TSM, she was a little more excited. Also, she really is a waterpark freak, so she loved the idea of BC pool. I just need to figure out how to add waterpark days. I may buy extra day passes and we'll stay in Orlando an extra day for a waterpark day. Although, of course, that gets into the super busy Memorial Day weekend....sigh.
Okay, I'm going to step back and just let things work themselves out. I'm sure we'll have a good trip.

All I can say is I'll be SO sad when my kids aren't super excited about Disney anymore. I hope it never happens!

Enjoy the trip you're spending so much time planning for!!

My kids are older and sometimes don't get as excited as I would like but once we are there that all goes out the window. They have a great time. A day at Disney is better than a day at home anytime!!!!:mickey:

This Louisiana family will be there at the same time period: I think that the thing to keep in mind, is that this is not your first trip, so you can pick & choose the rides to use FP for. Our family is also used to going in low attendance months, late Nov & early Dec., & I have also stressed a bit over the week prior to Memorial Day. I'm just keeping in mind that, it's not our first trip, & that the pool & weather will be a nice change. My plan is to be there at park opening & plan our FP times. I think the Disney magic will win over your child! Have a great time!

Goodness! Take a deep breath! This is your vacation too and you are also entitled to have a good time so try to relax a bit.

Since you've promised your daughter a water park, I'd try to set aside a day to do that and would likely head there first thing in the morning.

Crowds are beginning to pick up at the end of May so I'd expect moderate crowds. Still, I think you'll be able to manage the parks quite nicely, particularly if you utilize fast pass.

I think the pool at the Contemporary is quite nice and enjoyable.

If you're not sure where you'll eat on your arrival day, call Disney Dining when you arrive and ask what is available. You might be surprised at the options available to you. If all else fails, go for room service and pretend you'd planned that all along!