The Truth About Your Obsession with Vacation Planning

The Truth About Your Obsession With Vacation Planning

Your Obsession With Vacation Planning May Cause You to Miss Out on Some Great Parts of Orlando

If you’re obsessed with vacation planning, don’t worry. You’re in good company with a lot of other folks who choose a Walt Disney World vacation in Orlando.

If this is your first time, we really do encourage you to research and plan your Orlando vacation. It would be a shame to miss out on some of the things you would really enjoy if you didn’t do a little advance research and made some plans or reservations.

Of course, an obsession with vacation planning can actually cause you to miss out on some aspects of your Orlando vacation. If you’re busy running from ride to ride, you may miss out on some of the spontaneous joys that appear when you give yourself time to look around.

If you’re making a return trip to Orlando or Walt Disney World, we’ll give you some tips to make great plans while still leaving flexibility to change your mind and explore new options.


Welcome to the Orlando Local Show, episode twenty-seven.

William:   Thank you very much for joining us on the Orlando Local Show. Today’s topic: we’re going to be talking about whether you should plan out your Walt Disney World vacation or just wing it; kind of take it day by day.

Hi, my name is William Beem.

Lee:         My name is Lee Beem.

William:   We’ve done it both ways.  With a lot of planning and a lot of winging it!

Lee:         Yes!

William:   I guess there are kind of pros and cons to each way of doing it, but we kind of wanted to go over what some of those were so you can make a decision for yourself.

Before we get into the show, let me just say welcome to the Orlando Local Show. You can find show notes available at  and of course there is a free transcript of the show there.  We would love it if you would subscribe to the show on iTunes, Google Play or a number of other services.

Just go to  We’ll have links there for you to subscribe.

Let’s get down to it. Are you a planner or do you like to take it as it comes?

Lee:         I am a planner by heart.

William:   By heart you want to plan.

Lee:         It’s in my nature. I tend to plan things. It’s just what I do.

William:   Before we get into the advantages and disadvantages of whether you are planning it or winging it, I think it kind of matters if this is your first time. Like this is your first trip to Orlando and your first trip to Walt Disney World, because you might not really know everything to expect.

Lee:         You don’t. And you know what? Sometimes part of the joy of being there for the first time is not knowing some things so you can enjoy the surprises and discover things.

I think you have the two extreme ends of planning and winging it.  But it doesn’t really matter if you lean to one side or the other. I think more of it depends on what you’re looking for in your vacation.

Disney is not a typical vacation like anything else.  There is a lot to do; it’s a huge sensory overload, there are so many options and there is never enough time. Even if you don’t plan out day by day, having an idea of what is important to you and your family or your group of friends is, I think, absolutely essential for a first timer.

William:   I think one of the essential things to know is, are you someone who just likes to relax and just see what’s available to you, or are you someone who wants to experience everything that is there and make sure that you get a chance to take advantage of it?

Lee:         This is – yes – this is a very important thing to consider.

William:   You and I are on the opposite sides of this.

Lee:         Yes we are.

William:   You like to plan and I just kind of like to show up and say, “Hey, what’s here?”

Lee:         I do. Now I just want to clarify something.  When we started going I wanted to plan, but I always left flexibility within the plan.  Disney has made it a little bit more difficult to be as flexible as what you were able to be a few years back.

The FastPass Plus system where you are having to reserve and pick your rides and times, it almost locks you into a park for a certain time of day.  And they tell you quite happily that you can reschedule.

We’ve been there in the middle of summer and tried to reschedule because we had a change of heart and we had rides that we had selected staying onsite 60 days out; and they were headliners. They were high value FastPasses.  We wanted to change the park and there was really nothing good left there at that stage, so that also depends on the season and what’s available to you, but keep in mind that changing can work, depending what you are looking for, but it’s more difficult to  be able to just have a change of heart on the fly and switch things up now.

William:   I think you’re absolutely right. It depends upon the season. If you are there at a very busy time, whether it’s going to be the summer time when a lot of families are there or Christmas time when again, a lot of families are there, you don’t necessarily have the options to change because the park is so full. If an opportunity comes up and somebody cancels their FastPass and it goes back in the system and you want to try and grab it, well a lot of other people are trying to grab it too.  And they may get it before you do, the lines are going to be long and if you don’t have a FastPass to get on the rides or experience some of the other things that are going on at Walt Disney World, you are going to be waiting in a very, very long line and that’s going to take up a good part of your day.

Lee:         Yes.

William:   I’ve seen something as simple as a meet and greet with a character, like for example Merida when she came out – it was over a two hour wait for a lot of these families to go have their child take a picture with Merida.

Lee:         Well remember with Frozen – the stampede when the park opened to get there because not everybody could get a FastPass. It was kind of hiking up to almost three hour waits within the first hour of the park opening.  These things happen. Those are the extremes when something new and in high demand comes out, but it is a reality and you have to be prepared for it.

What I would say is that if you have – and often this is the case for families with very young children  - little kids get up early in the morning.  So it makes sense to just get up and go.

It is possible to do the things you want to do in the morning if you get there early for park opening, as long as you know where the high demand attractions are and you make sure that you knock these out first before the lines start to build.  I do believe it’s possible to do this without FastPasses.  Not everybody always wants to or is able to race back and forth across the park, trying to churn up everything in one day. And it might not be what you want.

William:   Well, let’s take a look at some of the advantages and disadvantages of planning.  One thing, I mean you were just talking about if you get up in the morning. If you haven’t planned, you wouldn’t even know when the busy times are.

Lee:         No, this is true. But I think there is a difference between research and planning. I think a little bit of research is absolutely essential.  And I see it as very different to planning.

Being aware of how things work is something that I do think everybody need to do. If you want to get the most out of your Disney experience you need to be aware of how things work, and the best way to do them to maximize your experience.

The planning is a very personal thing.

William:   And you went to, for me what I would call almost an extreme.  You created a spreadsheet.

Lee:        I did.

William:   Go ahead and tell me about that, because I have never made a spreadsheet to go to Walt Disney World.

Lee:         I had a color coded spreadsheet.  Each park had a color and I broke the day up into three or four sections. The resort and waterparks had a color as well.  So you could, at a glance, kind of see an overview.

What I would do was I would choose our highest priority things to do; they might have been rides, they might have been shows, but anything that was likely to get busy or lines would build earlier before the rest of the park got too busy, those were done in a darker shade which meant we would do these first.

Then the shade would gradually lighten through the day as things had a lower priority. And basically what that was, was those were the things that were most important to us during the course of that day. So for example if I had planned to be at Magic Kingdom all day for Tuesday, we would have Splash Mountain, Space Mountain, Big Thunder Mountain (that was for Tové and I). That would be in dark shade of the Magic Kingdom color, which for me was red.  Then after the colors would get lighter we might get to the medium shade and say, you know we are not going to stay here tonight. Let’s head over to Epcot.

William:   So you built in some flexibility to change your plans.

Lee:         I believe it’s absolutely essential because that way you don’t feel like you are completely locked in.  What made things very difficult for us was FastPass Plus because all of a sudden getting there early wasn’t good enough. It didn’t give you any advantage if you wanted to use the FastPass system other than maybe getting onto things before the lines build significantly.

William:   One of the things that I remember you talking about is you had your plan, you had your priorities that you want to go to, but then you kind of had some things “well maybe this, maybe that.”  But you’ve also told me that there were times that you and Tové would just look around and say, you know what? I don’t want to follow the plan anymore.

Lee:         Yes.

William:   Let’s go do something else. So I want to ask you two things. How did that affect your plan. I mean were you OK with just saying we are not going to follow the plan today and we are going to go wing it for the rest of the day?  And two, were you happy following the plan?

Lee:         Yes, to both.  We were happy to follow the plan because it meant that the things that were important to us were things that we got to do. There were rare occasions like sometimes you wake up and you are tired and you just think getting some rest and sitting around the pool for a few hours is more important than riding Splash Mountain for the 47th time this trip.

William:   Because if you have a full day in a park it wears you down. So the next morning you wake up and think, do I have to do this again?

Lee:         It does. Actually we ... we really used to burn the candle at both ends but it was part of the thrill for us. We had fun doing it and that suited our style. This is not for everyone.

But we enjoyed following the plan because it secured the things that were important to us. I would also say that my plan was designed to be abandoned at will.  And I specifically did it that way because we also loved not following the plan. Sometimes the nicest evenings that we had were when we had just completely broken the plan, decided to get on the monorail and go somewhere else. We ended up somewhere we hadn’t expected to be and just enjoyed it and I tried to build spontaneous relaxation in there.

William:   See that is one of the things I consider a disadvantage of the plan.  You follow the plan, you’re doing the things that you want, which is good, but you are not necessarily giving yourself a chance to explore something unexpected and something new.  As long as you are following the plan. Now when you abandon the plan, then you might notice things that are there that you hadn’t considered or didn’t know about.

Because Disney throws in stuff every once in a while that is unexpected.

Lee:         They do and this is true. I think that if you walk around and you are aware and you make the conscious effort to take in what is around you and just enjoy where you are right now, even with the plan you can enjoy it. You need to build enough reasonable time into your plan so that you are not literally racing from one thing to the next. Because you can turn up the pressure or you can dial it down a little bit as you please.

What I will say is that having no plan – those days, fortunately, were relaxation days, but there were some days when we got up and just didn’t have our act together and we sort of went OK let’s abandon the plan. But we really were wandering around aimlessly and it can lead to frustration. Because all of I sudden I felt like I wasn’t used to not achieving anything and when you’ve got a plan that allows flexibility you feel like even if you are just winging it and you have abandoned the plan, you planned to do that so ironically you feel like you are still sticking with your plan by giving yourself that time out that you’d allowed yourself to have.

I just like to have some kind of ... I don’t want every moment of every day to be mapped out. That is not a vacation for me. But I do want to know that things are important to me are there and I want to have the flexibility and a structure.

William:   Actually you used a work that just really stuck out to me. And to me it has no relevance to a vacation.  And that is because I usually like to wing it.  You said “I haven’t achieved anything.”

Lee:         But your view on this is very different.

William:   It is.

Lee:         You weren’t saving up all your vacation days, saving up all your saving money to go and make this an experience and I think a local’s experience at a Disney Park or I’d say even someone who visits very regularly (because things have changed for us).... The more we went the less important all these things became, because we had done them so many times and we were OK to give it a miss.

William:   Right, because you were traveling what, once a year? From the UK.

Lee:         Or more, yeah.

William:  Maybe twice a year and this was a special event. You were coming over here and you wanted to do all you could because you knew you couldn’t come back for a while and you’re not sure necessarily if you were going to come back.

Lee:         Right. You never take anything for granted, especially with foreign economy.

William:   But being a local here, and now you are too, I can go to Walt Disney World any time I want, which kind of sometimes means that well, you don’t necessarily want to go when you are not going to have a good experience.

For example, on some of the crowded days as much as I love seeing the Christmas decorations  - which we did go out to see  - I didn’t go a lot during the holiday season because the crowds are overwhelming.

Lee:         Yes. We went once.

William:   We went once this year and that is less than I usually do, but at the same time we have a family here and we had other things to do.

Lee:         Yes.

William:   But for planning a vacation I think that’s really what it is. Are you a planner and are you trying to make sure you see everything, or maybe it’s not your first time and you’ve been here a number of times and you think, you know what? Let’s see what happens because I’ve done all the rides, I’ve seen most of the things in there.  What have I not seen?

And what can still surprise me? I really believe that there are things that still surprise me. So for example on was it our last trip? I think – in the Magic Kingdom. You did something I have never ever seen or heard anyone do.

Lee:         And I do it a lot.

William:   That was over in Liberty Square and they’ve got the replica over there of the Liberty Bell.  And you reached in, you grabbed the clapper and you gonged the bell.

Lee:         I did.

William:   Everybody stopped and looked. I mean everybody.

Lee:         It was just dead silence.  The whole of Liberty Square just came to a standstill.

William:   I just loved the smile on your Face when you did it. But I thought about it and you had said, “You know what? If Disney didn’t want you to have that experience to see and touch and hear it, they wouldn’t have put a clapper in the bell.” Or they would have put up a sign that says Do Not Touch The Liberty Bell.

And you get there and you realize this is not a museum. This is a place where they want you to see and touch and experience things.  You are supposed to put your hands on things.

But most people never think about it. They see the Liberty Bell and think, oh that’s like a museum piece. I can’t touch that!

Lee:         Well you know honestly, they have got that fence around there and with my short little legs I really have to lean in to reach it. But there is no sign there. Had there been a sign there I would never have disrespected it and touched it.  But also, nobody has ever stopped me and I have done this in the presence of cast members who have high fived me on the way out. So I am assuming that this is not a problem.

William:   I don’t think it is. As a matter of fact, this is one of the things we are going to ask of you. If you are listening to the Orlando Local Show, which if you hear me right now, clearly you are! Next time you go to Magic Kingdom ring the Liberty Bell.

Lee:         Yes.

William:   Let’s make it a thing.

Lee:         I think we should. The Orlando Local Bell Ringers.

William:   And if you did ring the bell, let us know in the show notes at

Just put a little comment there and say “I rang the bell.”

Lee:         Yes. And also don’t go when it’s quiet. Because you just don’t get the full glory of the experience. Do it when there are people sitting around there.

William:   They stop and look.

Lee:         You can actually see them sort of hushed, whispering to each other and sort of glancing over. They don’t want you to see that they are pointing at you, but they are like “She just rang the bell!”

William:   And that’s something that most people would never plan to do.  That to me is a spontaneous kind of thing.

Lee:         It really was on that day as well, because I ran by and thought it’s been a long time since I rang the bell.

William:   But this is ... alright, let’s go over to kind of the advantages and disadvantages of winging it.

Now when you mention the disadvantages, if you don’t get FastPass or you don’t plan or for example, even if you don’t do your research and know that in the morning is kind of the best time to get in a line or something, you can miss out on a lot of rides.  Particularly on busy days.

Lee:         Yes.

William:   I think that a lot of that planning and saying, I must be here at this time and I must be here at that time, even within the range of FastPass, puts pressure on you. I want a vacation where I can relax.

Lee:         I do too.

William:   I don’t want to have to be anywhere at a certain time, other than my meals.

Lee:         Well, that’s true. I mean, I like a relaxed vacation – part of it – but I also like an active vacation. I needed to find a way and we perfected and adapted it over the years to suit ourselves and our own family.  But I needed a way to allow me to do both.

I’m not the kind of person who is happy to sit around and do nothing to relax or read a book for a week.  I really do want to get up and be doing things.  But I also don’t want to be running around under pressure all the time.

William:   I disagree with that. We went down to Sanibel and you went down by the pool and happily relaxed in the sun.

Lee:         I did!

William:   So you have your moments when you can relax.

Lee:         I do.

William:   I have a very different experience with Walt Disney World, having grown up here. I’ve gone there, I’ve seen it, I’ve done it and it is all very familiar to me.  There are things that I really love to do.  If I walk into Hollywood Studios I am going to hang a left and I want to go to Star Tours first every time.

Lee:         Yes!

William:   I’ll wait in the line, I’ll go do it. I really enjoy that ride.  And there are some rides like you really love Big Thunder Mountain, you love Splash Mountain, Tove loves Space Mountain.  Those are things that you want to do.  But other than that, once I’m in a park I like to look around.  I don’t necessarily just want to do the rides. I want to take in the experience.

Lee:         Well, I enjoy that as well. We both do.

What we did in our last two or three full on trips that we took was we had a challenge that every day we had to either do something that we had never done before or find or see something that we hadn’t noticed before.  And it was actually quite a fun challenge because you are partly looking, but eventually you start ... instead of looking around thinking what’s new? What’s new? You just have a sense of awareness where you are paying attention and you are a little bit more observant. And it’s amazing what you find.  We saw things that, after hundreds of days in the parks, we had just never noticed before.

William:   No and that happens. And you know this also extends to meals.  Everybody is kind of into the mood of breakfast, lunch and dinner. But you don’t necessarily have to do it at the time that most people take breakfast, lunch and dinner.

Lee:         We never did. For different reasons, but we never did.

William:   I usually like doing it off the time when I’m in Walt Disney World, simply because I want to avoid the crowd.  Maybe that’s a little bit of planning, but that’s like ..... I want to go avoid the crowd. So my plan, I guess, if anything, is to see where is everybody at? And not be there!

Lee:         Yes!

William:   And that works for me. It also gives me a chance to, like I said, experience things. I’m walking around, I’m looking at things. Most of my trips there in recent years have been kind of with a photographer’s eye. I always think, what can I take a photo of that most people may have missed. Or what is a memory that they have and would like to relive? And you’ve got to do that when there’s not a crowd around because otherwise, everybody is walking in front of your camera.  So that’s kind of really driven me to “What can I get?” rather than “I must walk in there and get this.”  Because that leads to frustration. If I feel like I’ve got a plan that I’ve got to go get something and something gets in the way of that ... we had that with a FastPass. We were trying to get on Big Thunder Mountain. We were in the middle of the queue and then they said sorry, the ride is closed.

Lee:         Yeah. They had to get us all out of there.

William:   So your plans are ruined and then you think, alright, what am I going to do now?

Lee:         It just messed things around. And it’s not ... these things happen.  It happens.  If you are there for more than a week it is probably going to happen to you somewhere, sometime unless you’re not spending a lot of time on rides. It’s just a reality of trying to run such high demand attractions. Things go wrong. Safety is always a primary concern.

William:   Oh absolutely. I don’t want to get hurt while I’m there. I don’t want to see anyone else get hurt when I’m there so I prefer that they shut down and say, look we have a problem. It’s a safety concern, it’s a mechanical concern. Whatever the case may be. Sometimes they don’t even tell you.

I guess if I’m in a plan mode and my plan just got disrupted, how do I recover from it.

Lee:         Well, if you don’t have kids it’s pretty easy. I can tell you right now no matter what you say, your kids are not going to see it this way. It is the end of the world. It is the worst thing that has absolutely ruined the vacation, we cannot ride Splash Mountain or whatever it is that you are waiting for, I don’t want to go and eat wherever we are going to eat, I don’t want to do anything else .... I’m giving you an extreme exaggeration.

Don’t expect your kids to let it slide as easily.

William:   That’s one of the advantages I find, of winging it. I am never disappointed. I don’t have an expectation when I get there so I’m never disappointed.

Now like I said, if you’re a first-timer and you know of certain rides and you go there on your vacation and you never get to them because you didn’t plan for a FastPass you may be disappointed.

Lee:         And also you know, for some people this really is a once-in-a-lifetime visit. Disney is not a cheap vacation.

William:   No it’s not.

Lee:         Most people put a lot of sacrifices and saving into this. This is a big deal. It’s not just that it feels like it; it really is a big deal for anyone who is planning a vacation. For someone who is going on their once-ever trip to Disney World and they have one day in the Magic Kingdom and the ride you’ve got your FastPass to ride shuts down ... I know that we need to let it slide, but I totally get it. Because in a situation like that it is a big deal. So I’m not going to suggest that someone is silly for getting upset because I can tell you now, one day, once only? I would be absolutely gutted about it.

William:   I believe that.  You know the reason that this whole idea came to me is I read an article about people who are wasting their day at Disney World because they don’t plan.  And I thought, how arrogant is that?

Lee:         It is. It’s a very general blanket to cast over people because there are so many different classifications of type of visitor and the purposes for visiting and your family structure. I mean the list is just endless.

You need to do what suits you and what makes you and your family happy. But if you guys are happy, you have done a perfect job of executing your plan or no plan, or whatever you’ve done and I think that’s the way you need to look at it.  Don’t let somebody tell you that because you are doing something differently to the way they do that it is wrong. There is no wrong if it’s right for you.

William:   Thank you very much and that covers our show for today of whether you should plan your Walt Disney World vacation or wing it.

My recommendation really is a bit of both. I like the idea that you plan the major things that you want to see, but you’ve also left room to go explore or change your mind if you want to.

Lee:         I make a plan that is intended to be abandoned somewhere.

William:   There we go!

Thank you for listening to the Orlando Local Show.  Show notes are going to be available at  and of course you can find a free transcript of the show there. We would really love it if you would subscribe to the Orlando Local Show. It’s easy. We send you off to

and a few others. We will put them on the show notes.  Have a good week, everybody. We’ll see you next time.

Get Free Updates of The Orlando Local Show

Discover More Episodes!
The Orlando Local Show Podcast Library

The Orlando Local Show podcast library is here for you to search and listen to helpful episodes about Orlando.

Listen Now

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *