1) Feeling ashamed when in line at character meet and greets.
Ultimately, when you think about it, if you're in line with children behind you, you're taking away the potential time from them that they could have met their favorite princess or character sooner if you weren't there and then you start feeling ashamed. It's a matter of ethics, but who can resist meeting royalty or maybe even a childhood hero? You get the evil eye from the parents. Second thoughts?
Just think about the inclusion that is Disney World if this scenario is getting you down. It's a space for everyone to have fun and feel something special. Some youngsters might even be afraid to meet the characters, so maybe standing in line and watching you interact with the characters could let them know that everything should be all right.
2) Not bringing enough money.
Let's face it, we could spend a small fortune at the Marketplace Co-Op in Disney Springs or Mitsukoshi at World Showcase's Japan or Tangier Traders at Morocco (both in EPCOT). Having a spending limit (and sticking to it!) before you head out on your trip will help make purchase decisions easier. Don't be afraid to buy something in the parks, especially if it is a specialty item that you cannot get elsewhere.
Pooh and Tigger Character Spot
There are a lot of ways to save and make money throughout the year (giving blood and plasma?! All I can think of off the top of my head...oh, and mowing lawns?) and the Budget Board has a lot of great ideas. There could be double shift opportunities at your place of employment during the holidays that could get you some extra spending cash... there's a trade off, though - no family time for one day versus lots of family time on vacation-it's your call and everyone's situation is different.
3) Settling on quick service/not experiencing signature restaurants.
Don't get me wrong, there are a lot of quick service locations that I enjoy. They are convenient, comparable to fast food outside of the parks (don't waste time leaving the park!), and they should all accept the Dining Plan. Grabbing a quick bite to eat in the middle of shopping at Disney Springs may even make more sense than to suddenly stop what you're doing just to go to a reservation in a different area. However, going to a few table service locations, I can tell you that the food is just more complex and tasty.
What this boils down to is that you're missing out if you don't take the time to make a reservation. Be Our Guest Restaurant would be the gateway to get you there. I know the phone is a scary item, especially to people with social anxiety, but there's hope, since you can usually get the reservations you want on the Disney website if you're 180 days away from your trip.
4) Skipping an attraction to ride later, but the park closes before you return.
You might have a reservation on the opposite side of the park, a line is just too long, or the time to meet up with your friends or group is creeping up on you, so you decide to skip the attraction and come back to it later. I know it's a horrible feeling when you find your way back and the queue line is still long, or the park is closing.
Shop in Morocco at World Showcase.
Remember that Extra Magic Hours may not include an attraction that you want to experience, so don't bank on that. Ride what you can, when you can. Adjust your plans to have some flexible time slots and keep an eye on closures and refurbishments before (and even during) your trip. Also, watch for soft openings for new attractions!
5) Not enough energy.
We all know your feet hurt and you should probably take a break before you make the trek over to Expedition Everest, but the park closes in an hour and do you just end up regretting not going or do you punish your feet to the point of blisters just to experience this attraction?
Innoventions' best attraction!
I usually walk about 3-4 miles a day, but I think I can handle 10 miles a day. Stopping to eat and standing in line are alternate forms of a break, right? WRONG! Build up your stamina before you go; you should already know your goals. Animal Kingdom is probably the park I will walk the most in (probably why I mentioned Expedition Everest earlier), since there are many shows to experience spread out to the extremes in the park, so our group always ends up crisscrossing paths - even though we know we're trying to stick with a walking plan.
6) Drinking too much/not staying hydrated.
So, on our first trip together, my wife observed a group of friends going around World Showcase and drinking heavily (and this was not during the Food & Wine Festival, by the way). A certain person couldn't handle it (they were passed out in the bushes) and we later saw that person on the way out of the park... their group had rented a wheelchair to keep them together with the group (because they were still passed out). There are many ways to enjoy the parks, but drinking so much that you can't enjoy all that a park has to offer is not one of them. Please, drink responsibly.
Also, you must keep hydrated since you're going to be walking around a lot (and usually in the heat). If you can't stand the notoriously bad-tasting, 500 mile, underwater system that is the source for the fountains (and ice machines in the parks), try a filter that goes into your water bottle. It's a small item to pack, but hassle-free. No sulfur taste!
7) Not staying enough days.
Ah, yes. You were concerned that a first-timer in your party wouldn't find all of this "kid stuff" appealing, so you held back and only planned a four night stay (that's what they advertise anyway, right?) only to find out that they're begging to stay longer now. It's a tough balance between what's right or appropriate for everyone in your group and what's available or financially feasible.
There are many ways to keep the magic going, even if you're not on property anymore. Until your next trip, reminiscing about the last one will spark positive conversations and can instantly turn frowns upside down. Learning what worked and what didn't work from that first trip will help you decide how adventurous you wish to be when planning your next trip!
8) Getting around without ease.
Is there a bus that goes from Hollywood Studios to Animal Kingdom? Does the Ferry Boat only go to the TTC? If my reservation is at a restaurant on the Monorail line and it closes, how do I get back to my resort? Does this attraction require me to transfer or is there a wheelchair-equipped ride vehicle?
Doing your research can save you a lot of headaches. For example, know how tall your children are and which attractions they can enjoy. Find out alternate ways of getting to the parks in case something closes or cancels. Vacations should be fun, worrying about getting around is not.
9) Forgetting items in your luggage.
Some stuff you can replace, like sunscreen, over-the-counter medicine, clothes, towels, moleskin, etc., but other things like prescription medication, expensive video cameras, and your MagicBands could cause a small panic if you realize you didn't pack them.
Any bench will do when your feet are hurting.
...and don't forget about your furry friends! Make sure there's a plan in place if they aren't going on vacation with you (or if they are, there's a kennel called Best Friends Pet Care near Port Orleans Riverside). You wouldn't want to worry about them.
If I fits, I ships?