I think part of a Disney trip is the anticipation. (That’s one of the reasons I'm generally
not on the “surprise” side of the “should we surprise the kids?” threads.) Not that I’d turn down a free spur-of-the-moment trip or anything!

But I do understand what you mean.
I was thinking the same thing. We had just one trip where we surprised the kids, and we decided it was fun to do once, but we wouldn’t do it again, because the trip seemed so darned short because they didn’t help in the planning, and that’s really half the fun! It was their 8th birthday, and we picked them up from school. We’d told them we’d be taking them to McDonald’s Playland for their birthday

but instead, we had everything packed and in the back of the car. We wrote a big poem about the ruse, and they had to read it (while still parked outside school) before they figured out what was going on. We watched the video of it recently (so grateful DH was so handy with the video camera back then!) and DS, while DD was reading the letter, kept saying, “We’re going to Disney, aren’t we!”. It was cute. So finally as we pulled away, you hear DD sort of quizzically say, “So does this mean we‘re not going to McDonald’s Playland?”

(She loved it there, too!)
I have been thinking all day about which trip of ours was a “bad trip”. Really none of our trips were bad, except one was hard. About a week before our first
Disney cruise, on which our kids would be turning six, I was diagnosed with breast cancer. (Have learned never to schedule tests like that before a major vacation now if I can help it.) We were going with friends who offered to postpone, but I didn’t want to disappoint the kids, or any of us, really, as we were so looking forward to it. And I got my doctors’ blessing as they said I’d have a long year ahead of me when we got back. So we went, but it was bittersweet, because so many amazing moments were tainted by that awful feeling of dread you get when something bad is happening in your life. The friend who came with us, a nurse friend, was good about letting me vent or cry if I needed to, but I tried not to. One day as we were eating breakfast I noticed a family beside us with a Make A Wish kid, and that turned it around for me as I realized I was glad it was me and not one of our kids. That gave me a new perspective, and I went from worrying about it, to gearing up for the fight. As we were leaving the ship, DH told me I’d just have to book another cruise for when my treatment was over, so I did, right away, and that planning is what helped me get through the next year. (And was how I wound up here!) The following year when we crossed the threshold to enter the ship, after being battered and bald much of the year, DH and I looked at eachother crying tears of joy and gratitude.
A couple of moments I can think of that were not so nice. One, on the first trip DS was tall enough to go on Space Mountain. He enjoyed it one day with DH, then on the second day, while he was in line, they measured him and one CM said he was too small to ride. We tried to talk to the CM saying he‘d gone on the day before, so the CM bent down to DS and asked, ”How did you like the loops?”. DS, a little confused to what was going on, said ”good”. The CM, in front of everyone in line, said, “There are no loops on Space Mountain, so you couldn’t have gone on yesterday”. And with that, we had to leave the line sort of shamed, as if we were liars. It felt like he needlessly humiliated a little boy. DS is shy, so that was pretty devastating to him! Karma, is all I can say.
Another disappointment was on a trip for the kids’ 21st birthday, I’d booked a couple of nights in a Club Level room that I’d found on Priceline. Great deal. On the morning of their birthday, they went to order a Mimosa at the club lounge and lo and behold, they wouldn’t serve them because their licenses expired at midnight - on the
night of their birthday (seventeen hours later)! And the rest of the trip was hot and cold as to whether they’d get served. World Showcase was pretty good, but the resorts were strict about it, saying they could get in trouble. They did make it up to us, but what a bummer that was for a trip we’d planned for many years! (If they had gotten new licenses before we went they would’ve had to get junior licenses, apparently, and they wanted the adult version. I had no idea about any of that prior to leaving. Oh well, live and learn.)
Another time there were 30 of us who’d gone on a land-sea vacation and booked a private bus for the three way transfers. Well the bus never showed up to pick us up at the cruise terminal so it involved a lot of frantic phone calls, standing around waiting for hours, and some of us almost missing flights home, etc. The company acted like it was no big deal, either.

We like having our own car. Although we once had a rental that wouldn’t start when leaving for the airport to go home and we had to leave it there with the keys locked in the resort safe by the manager, as we were on the last flight out of the night. Total headache with rental company for days afterward, but finally that got resolved, too. I’m careful who I book with now. That same trip my boss had also texted me about a work issue that could’ve waited and put a bit of a damper on the trip for me (the same trip as the license and car issues) so of all our trips, that one was probably the one with the most frustrations.
@apirateslifeforme, Omg, what an awful experience on Jungle Cruise! That guy sounded unstable!
And to those of you who’ve experienced sickness while on trips, injuries, or other problems, ugh! We‘ve somehow managed to avoid illness there, thankfully, however it seemed that almost every year when we were up in NH we wound up in the ER with DS from either an asthma attack or an injury or fever or something.
@Bianca and Bernard We’ve had our dog at the kennel at Disney, too, and I agree, it was not a great experience! I was surprised to see your post because most posts I’ve seen here are generally favorable. They tried to force me to allow them to give my dog a flea bath when he was negative for fleas on check in (via flea comb) AND he was on a flea and tick pill monthly! I refused to sign the paper for a flea bath and they were so pissed at me!! He could’ve become toxic from the chemicals and they didn’t seem care, only wanted the $$. And while there he developed a really nasty eye infection that he didn’t have before! Tons of green guck coming out of both of his eyes! Thankfully I had some ointment with me that cleared it up but that grossed me out a bit. He has picked up mild cases of conjunctivitis at both his home kennel and a groomer’s before (just twice), but this was a whopping infection that came on very fast. And now that I think of it I believe he also got kennel cough that trip (college visit where we drove) even though he’d had the vaccine. Oh, and that same trip (the only one where we’ve had the dog with us) we were in line for Mine Train close to midnight, and almost to the front, having stood in the line for close to an hour already. We’d never been on it before and I was so looking forward to it. When I happened to glance down at my phone and saw that the hotel had texted me to say could we please return because our dog was barking and people were complaining. Omg! We debated for about a minute what to do, since we were so close to the front, but decided to leave to go back right away since it was so late. So there we were walking out the side gait to leave. Dog had been fine in hotels before, in his crate, with the TV and soft lighting on, etc., but what happened that night was that DS had forgotten his hat in the room, so went back in and switched the lights on, and I think the dog must’ve somehow thought his barking would get us back again, so that was a bit of a bummer, too. Had to wait until the next trip to ride the Mine Train! (And it’s now one of my favorite rides at WDW!)