Surprise Trip to Walt Disney World

Is a Surprise Trip to Walt Disney World Right for Your Family

A Surprise Trip to Walt Disney World Can Go Either Way

Your surprise trip to Walt Disney World could make you feel like a hero or a fool. Give it some thought before you decide to tell your family to drop everything because you planned a surprise trip that they weren’t expecting.

Thank you for listening to The Orlando Local Show. We have a bit of experience with the surprise trip to Walt Disney World and can share the positive aspects, as well as some potential negative issues.

If this is your first trip to Walt Disney World, we recommend that you may not want to make it a surprise. There are some benefits you get when looking forward to a trip for a while, as it builds anticipation. Don’t overlook the value of that anticipation, because your trip may be anti-climatic without it.

Also, it’s easier for your family to know what they’re getting in a surprise trip after they’ve already been to Walt Disney World. You may find that you won’t have to face a barrage of questions, too. Your family knows what to expect when you surprise them.

We have plenty of other recommendations in this episode, but one of the biggest is to avoid misleading your family about a vacation. They may get excited about the fake trip and be disappointed if you pull a switch.

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William:    Welcome to the Orlando Local Show. My name is William Beem. Lee:     Hi. My name is Lee Beem.

William: And today we want to talk about something a little unique; maybe it’s not so unique because I guess a lot of people do this. We are going to talk about a surprise trip to Walt Disney World for your children.

And you’ve done this at least once before.

Lee:          Only once. That’s what I always said. Only once.

William: Before we get into our topic, I just want to let you know that show notes are going to be available at and of course you can find a free transcript of the show there. And there will be links to subscribe to and to the Orlando Local Show. We would really love to have you as a subscriber. You’ll be our special friend.

Lee:           Yes. Forever!

William: OK, today’s topic: we’re going to be talking about surprise trips. And this is something that I know people do it and you can see videos on YouTube when somebody goes and tells their kid there’s going to be a surprise trip. Drop everything. We’re going to Walt Disney World right now!

Lee:           Really? Like today?

William:     But the thing is there are times when you want to do it and maybe there are times that you might not want to do it. So we are going to kind of go over a little bit of each and let’s just start off with why you want to do a surprise trip for your kid?

Lee:          This is something that’s fun. What prompted me to do it was the first time I booked a vacation to Disney World we had almost eleven months of the countdown. The kid was five at the time that I made the booking.

Eleven months for a five year old feels like their whole life and eventually it got to a point where this was just never going to happen and it was almost like she’d run out of steam; there was no excitement left by the time we were getting ready to go. I mean on departure day it all came right back again, but it became very long and tedious. Not a

day went by where I wasn’t asked how many days until Disney World. How many sleeps is that?

William:     It really is something special and fun for your family. You mentioned there is a long countdown so we are talking about children that are

younger and don’t necessarily have a concept of how long it’s going to be or even I think if you’re a teenager. It’s like OK I’m still waiting!

Lee:           Yeah, I think teens have a better ability though, to use that time and get distracted with other things.

William:     It’s in the back of their mind somewhere. Like the idea is that you are still doing the planning. You are still getting everything ready as adults. But for your children you’re kind of not letting them in on it so they don’t have to worry about it, they don’t have to deal with it; they are not going to tell their friends and then their friends say, “Well when are you ever going to go?”

Lee:           Yeah.

William:     At least that’s the idea behind it. You want to make them happy. You want to avoid all the delay and wondering and all the questions maybe, that go with it.

Alright, so you’ve made the decision that you want to have a surprise trip to Walt Disney World.

Lee:          Yes.

William:    What do you have to think about when you’re going to do this?

Lee:           The first thing I’d think about is if it’s a surprise trip, what is the risk of her finding out? And my view was every person you tell significantly increases the risk. They don’t have the same investment in keeping the secret that you do.

So I decided not to tell anybody. Nobody knew where I was going. Just let them know we were going to have a vacation sometime over to Spain. I hadn’t said anything to Tové yet. I didn’t lie about it. We had

actually been looking at going to see some friends there and I just left it loose and casual and didn’t say anything to anyone. Even my parents, who drove us to the airport, to the hotel – the overnight hotel – didn’t know that we were going to Disney until they came to load up the luggage and my dad said, “That is a lot of luggage!”

William:     Well, actually you kind of brought up something. It’s one thing to want to do a surprise trip. But another thing is, it can backfire on you. If

you’re trying to keep this a secret.

Lee:           Oh, just search Disney surprise trips gone wrong on YouTube. You’ll be watching for weeks. And it can go wrong.

William: Well, one of the things you mentioned like “Oh we’re thinking about going on a trip to Spain.” OK, great. Your kids get the idea. It’s like, we’re going to Spain!

Lee:          If you tell them that you’re going to go and do something on the

assumption that Disney is going to be better, don’t count on it. I had a child who I knew if I promised her something no matter what I offered her, when I said something was going to happen that was what was going to happen. So I did not want to mislead her. And that is why I didn’t tell stories to other people either because I didn’t want it to slip and her to think she was going somewhere and work up excitement and suddenly this is instead of ...

William:     So what is your advice? Basically don’t tell anybody you are going anywhere?

Lee: Well you might need to tell somebody. I mean this depends. You might need help and support. It may be that you need ....

William:     I think as you get closer like taking care of the house or maybe you have pets and need someone to take care of them, you need a ride to the airport and that sort of thing. But you don’t need to necessarily do that if you are planning up to a year out or so.

Lee:           You really don’t. Certainly not in the initial stages.

William: Does it matter how many children you have? You and Tové went and it was just the two of you. But if you have multiple children, especially if they are at different ages. How does that impact your plans?

Lee: I think it has a significant impact on your plans. It was much easier for me only having one. She had been before. In fact when I booked the trip I’m not even sure if it was before we came back from our next trip at the time. So we were ... we’d made at least two consecutive trips already within the space of less than a year. So that made it, I think, a little bit easier for me to get a fair idea of what she liked and to plan around it on her behalf. Because bear in mind if your kids like to be involved in the planning as part of the build up, they are not going to get this if you exclude them right until the last minute.

So make sure that is not going to be an issue. I think that becomes more of a problem when your kids are a bit older if they show an interest in planning and expressing their views. But because of our past Disney trips and it was so important to her and something she had enjoyed so much it was pretty easy to slip in, “If we go back to Disney one day, what would you ...?” and then ask the question.

William: OK so that way you would ask questions without necessarily tipping her off to the fact that you’re going and when you’re going.

Lee: That’s right. So she was feeding me information and I just had a little notebook and I was keeping notes on anything, which I used for my planning.

William: Now does it make a difference if you’ve never been there before or if you have? I guess you could ask, what would you like if we went to Walt Disney World?

Lee: I think it’s harder if you haven’t been before.  I also think it’s harder and there’s just so much that is involved in the planning and the research because they’ve made it so there is too much to do in one vacation, no matter how long you stay.

William:    Yeah, they want you to come back.

Lee:   Even if at the time you’re going to run out of energy!  I think having the benefit of past experiences and just knowing how to structure your day could take a lot of pressure off. Because when you plan a surprise trip there is almost in increase in the level of responsibility that you feel for your kids to have fun. I don’t know. It’s a really strange thing.

What I would say is one of the down sides of a surprise trip when you don’t tell anyone is I realized by the end of it that it was such an anti climax. For me the whole ... there was no build up. Nothing felt real. It didn’t register. I got on the plane and I was waiting for that “I’m going to Disney” feeling and it never really came because I hadn’t been able to express it. I hadn’t been speaking to people about it. Nobody was asking me questions or what are you looking forward to?

William: You know, that is something that I guess people don’t think about but it’s a real part of your vacation. You want that build up.

Lee:           Yeah.

William: And if you’re doing this by yourself and you keep it all to yourself and then you don’t get to share that with anybody, they don’t get to ask you any questions and there really isn’t a build up.

The next thing it’s like you’re going. Hop on the plane.

Lee: Well that’s something else. If you’re doing it as a couple I don’t think you have quite the same problem with that. There are two of you and you can bounce it off; maybe you’ve even got one or both sets of parents or some cousins or somebody else coming with you. Those people are obviously going to be included and going to know to keep the secret.

William: Here’s another problem that I can see coming to mind. If you don’t tell your child what you’re planning on vacation and they know that pretty much every year, if this is the way your family works, that you have a summer vacation or whatever the vacation may be.

Lee:          Yes.

William: They may start thinking about something else and start asking you, “You know what? I’m really looking forward to going to ...” wherever. And they start hitting you with that because they are building up in their mind, “I want to go to this place. I want to go to New York. I want to go to Miami. I want to go to the beach somewhere.”

Lee:           Well, that happened to me.

William: And then you’re thinking of this trip that you planned or you’re planning in your mind and you can’t tell them. Like no, we’re not going there. Well why?

Lee: Well I didn’t actually do that. She was asking. We had some friends in Spain who had come over to see us a number of times and they had invited us to go over and spend some time with them. I was seriously looking at doing it. It was just going to be maybe a long weekend or something so I didn’t commit to it and I didn’t tell her we were going or when we were going, but when she asked I just said to her I hadn’t dismissed the idea. It was just a case of finding the right time. So she knew that plan hadn’t been abandoned, but also hadn’t been cemented in any way yet. And that’s how I dealt with it. I didn’t want to build her hopes up towards something that I knew wasn’t going to happen, but also because I genuinely hadn’t dismissed it, I just said to her I am not at a stage where I can make these plans right now.

William: One of the things I was wondering about was unexpected reactions. Like you build up to something; I’m doing something wonderful for my family. I can’t wait to tell them and then you tell your child, “We’re going to Walt Disney World. I’ve got your bags packed. Let’s go.” And then what happens?

Lee: It can be anything and I can just say you think you know your kid? I mean I know that if ... I had to watch the reaction unfold. I am guilty of this. I tend to suffer from a bit of a delayed reaction issue when something catches me off guard. I just sit there completely dead-pan. It has to process through my head. This is exactly what Tové did. She stared at me and she laughed.

William:    She laughed at you?

Lee: She did! And she said OK is that for next year? And I said to her we are going tomorrow. And she looked at me and laughed again and she said, “No, for real. Come on Mom. Is it for real?”

I said, “Yep, for real.”

She said, “Do you have tickets?” And I said yes. She said, “Well I want to see them please.”

As the evening progressed I then took her out for dinner and my family was there as well and so we enjoyed some time together. You could see as it started to register, the excitement was building.

So it wasn’t an anti climax, but I also hadn’t built myself up to expect anything specific. I just knew that she was going to be surprised and I didn’t want to tell her on the day of departure because my child did not like to be put on the spot. She needed that time to process things and I knew it; which is why I decided to do it the night before.

William: So it’s really important to understand how your child is going to react to something before you plan when you’re going to tell them.

Lee:  That’s right. I needed her not to be asking questions while I’m trying to go through security because you know you’ve got to go through various processes and you need to do things and it could be anything... the kid has got one thing on their mind. They do not have the same responsibilities you do and they want you to tell them now, because it’s really important.

This is going to vary. You’ve got ... you know sometimes you’ve got a few siblings with varying ages and the older ones are sometimes just so cute and adorable with the younger ones and they kind of help explain things.

William: Is there a down side to saying pack your bags. We’re going right now or we’re going tomorrow? Or do you want to give them a longer, like maybe a week’s notice, or something?

Lee: I’ve seen that work as well. And some people do that and I think it can be a very smart move.

There are no rules other than think carefully about how your own family reacts and also think about the time that you might need. I told Tove in the evening and then expected her to go to sleep for an early wake up. Well she didn’t. She lay in the bed in the hotel and talked persistently until I even just disabled the alarm because we were still awake. So take these little things into account. They are going to be excited. Hopefully.

William: Here’s kind of the last question I’ve got for you. So you’ve done all the planning and she didn’t really get a chance to give any input to it. Did that have any impact on the vacation? I mean you know your child and what she likes, but did it make a different when you involved her in the planning ahead of time versus whether you decided everything for her?

Lee: At that age, no it didn’t. I had always involved her in the planning, however that is why I’d asked her things and made the notes because when she said, “Oh but you should have told me because I would have asked ....” and I said to her, “Don’t worry. We’ve got that covered.”

Because things had been coming out in discussions just in watching some Disney YouTube videos and then she’d say, “Oh I want to do that. Next time when we go back one day, I want to do that.” So I was kind of keeping notes. So she actually did give input. It just wasn’t in the conventional sense.

William:    OK. But you said you only did this once. Lee:   I only did it once!

William:    What made you decide that you didn’t want to do another surprise?

Lee: I think I knew that before I’d even executed the surprise. And that is because my dad used to surprise us with taking us away. It wasn’t Disney World trips, but he used to just come in and announce things. And it wasn’t that he tried to surprise us, but he was just quite impulsive sometimes. And he’s say, “Right, guys pack your bags. We’re leaving now.”

Where are we going

“I don’t know. We’re going to get in the car and drive. Be prepared to stay out for the night.”

You get to a point where you almost anticipate the unexpected and I didn’t want her to start thinking, “OK, if I haven’t heard anything for a while [because you don’t know what’s going to happen in the future] well where is my surprise?” So I figure once you’ve done it twice, it is almost starting to set a trend.

But I think the main reason is once we got back I knew I had no regrets at all. It was a wonderful thing. I’m so glad I did it. She still speaks about it as one of her best vacations, but that anti climax that I felt going into it was pretty hard. I struggled with that. I felt like I’d spent this long build up, put in so much work and kept a secret and I also wanted to get excited about it. But it wasn’t even that. I mean that was kind of funny watching her with it, but I just didn’t get that “I’m going on vacation” feeling. And I missed that.

William: Yeah, I understand that. And I know what you mean about like your dad coming home with a surprise because I grew up here in Orlando and every once in a while my dad would come home on a Friday night and say, “You know what? Let’s go to Walt Disney World. “ And I’m a kid, I’m excited and it was much more affordable for a family to do that then. I think it cost us like $14 to just drive over there and we would spend the day. It wasn’t the same thing like taking a trip where you’ve got to plan hotels and air fare or whatever else might go with it. It was really cool when you were a kid and your dad comes home and says, “Let’s go to Disney World tonight.”

And we’d go there; we’d have a great time. And I loved that anticipation. I know what you’re talking about. But alright I said a last question, but I changed my mind. I do have one other last question.

Lee:          OK.

William:    Would you recommend a surprise trip?

Lee: There isn’t going to be a yes or no answer. This is actually a very highly controversial discussion. There are people who have had really good successes and have done it multiple times and it’s just been something they’ll never forget; absolutely positive. And they are going to recommend it.

But there are also people where it’s turned into an absolute disaster and a lot of the time this has been because they have worked the kids up to expect something. “We’re going to Grandma.” And they’ve been excited and then ... well that means we’re not going to Grandma! Kids want both. They want something extra. What happened to the first one?

William:    Yeah, why can’t Grandma come to Walt Disney World with us?

Lee: Exactly! So I would urge you to be very cautious of what you say to  your kids. But you know, you know your kids. It’s not for me or anybody else to tell someone how to approach something like this because every family dynamic is completely unique.

William: I think that’s really the advice. Before you make the decision to have a surprise trip you really need to think it through for your family. Like what are the reactions going to be either way?

Lee: You really are the best qualified person to make that decision. The only qualified person to make that decision. And you can get some input from others to help you come to a decision on this.

William: With that in mind, this is what we’ve learned about taking surprise trips. We’d love to know if you’ve had any experience. Leave us a comment at

Thank you so much for listening to us on the Orlando Local Show. We really appreciate you. As I said at the beginning, show notes are available at and of course you can leave us a comment there if you’ve had a surprise Walt Disney World Trip. Let us know how it worked out for you. And if you have any advice for others, please leave it there. You can get a transcript of the show there for free and of course there will be links to subscribe to the Orlando Local Show podcast.

Thank you so much. We’ll see you next week.

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