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giant fireworks and smoke surround the Disney castle during a lights and fireworks show!

Top First Time Disney World Trip Mistakes

There are almost countless Walt Disney World lists out there.  Many of which can be found on our own site here. However, there certainly is some value to these lists and I even appreciate all of the various opinions expressed in them.  This list (or guide if you will) might be a bit more opinion than some of our other pieces. What we list as mistakes others may very well see as a must-do. Please, take advantage of our experience and perspective, use this information to make more informed choices with what works best or is desired for your vacation.  After all, helping you is exactly what we’re here for. We love it and appreciate that you give us the opportunity to help make your Disney dream vacation come true!

That first trip to Walt Disney World can be an incredibly painful “learning experience” that comes with discovering how easy it is to make a mistake. As we discussed in our previous Reasons Why Heyday Travel Agents Make your Disney Trip Better, we’re here to help reduce that pain.  Even with the best of planning and help, take some solace in the fact that everyone experiences some mistake on their first trip. No amount of planning can prevent the inevitable error. As I type that I realize that may create more concern than it does soothe. Just know, you’re in good company and sometimes with the passing of time and retrospect, those mistakes make for great stories. ;) Like the time I went to Legoland with my son and we found it was closed that day! Let’s begin.


image shows various lines that represent the average high, average low, record high, record low, and average precipitation throughout the year for Florida weather.

Even more specifically, not packing for the Florida weather that you’ll be experiencing.  Although known as the “Sunshine State” this isn’t always accurate. Plenty of days are overcast, cloudy, and we can’t forget the rain that comes through almost daily.  Although, while snow is incredibly rare, that doesn’t mean that it doesn’t get cold.  

The weather in the area can fluctuate widely and dramatically.  How about a 30-degree swing? It can easily be high 40’s/low 50’s when you head out in the morning, hitting 80 in the afternoon, and hitting low 60’s before you’re back to your resort at night.  We suggest using our Orlando, FL weather resources tab averages during your planning phase and then check back for actual forecasts as you get closer.

We are always focused on setting expectations and this is easily one that gets overlooked.  Just because it is sunny doesn’t mean it’s not cold. Just look at nearly any marketing photo for ski resorts!  Late fall to early spring you can easily see temperatures range from freezing to 80’s over the course of a week.  At least during the summer, you can count on high temps, high humidity, definitely sun, and don’t forget the inevitable afternoon shower or occasional thunderstorm.

The important thing to remember is to be flexible and pack for a variety of weather conditions.


Disney Mickey Mouse icecream bar

This one may raise an eyebrow or two.  Yes, it is your dining plan and you’re free to spend it as you see fit.  All I’m saying is that you may want to be a bit selective about where you spend it.  I love a good Rice Krispie treat as much as the next person, my wife may even say my belly testifies a bit more than most.  However, there are plenty of other options to consider before making that your go-to treat.

Our suggestion is that before you use all of your snack credits on those, you take a look at some of the other delicious items you can get.  Avoid the pre-packaged goodies and enjoy some of the freshly baked or frozen goodies that you can find all over the park. Or, in our opinion, if you are going pre-packaged get a classic Mickey Bar ice cream. If you have leftover spending, some packaged goodies make a great “souvenir” to bring home!


Christmas decorations at Disney World during a busy, but magical time of the year!

If you choose to go during a major, or even some minor holiday, don’t be surprised by the crowds.  I’ll let you in on a big open secret, there is never an absolutely slow time at Disney. There are always people there! (I mean, it is the most magical place on Earth). The easiest rule of thumb to follow is to look at a typical school schedule. If there is a time that most schools are out, Disney is likely to be busier.

This doesn’t mean that you can’t have fun at these times.  In fact, Christmas is one of our favorite times of year to go! We’re just looking to set expectations with what you may encounter.  Some longer wait times, higher levels of competition for ADRs, etc. Still, we suggest not making a holiday trip your first experience.  Disney can already be an overwhelming experience, you don’t need to add excessive crowds on top of that. If that’s your thing, then, by all means, we would still be happy to help with any planning.


A giant mac n cheese burger with a pickle, side bucket of waffle fries and a dark colored pop from Disney.

… at the counter-service restaurants.  I’m not saying you have to avoid those items, per se, but not eating only those items.  We are well aware of the reputation that theme park food is overpriced and ‘meh’ at best.  Some of it is and they are absolutely taking advantage of the captive audience and charging more than they would off-property. This is not necessarily the case with everything that Walt Disney World offers.

Plenty of locations have your standard fare (see the title). Many have some very interesting and rewarding dishes too. Many of which aren’t significantly more expensive than the titular offerings here. Even Casey’s Corner, known for their hotdogs, takes them a step above what you might find at a street vendor.

This part also ties back into the planning pieces we’ve mentioned before.  Something beyond that stock fare is more likely to be found at a table-service restaurant.  The same ones that start taking dining reservations at 180 days before arrival (see our planning timeline). If you missed that reservation window, you may miss out on some amazing food and be stuck eating only burgers, hot dogs, and pizza. We take care of reservations for you, so please don’t hesitate to reach out with any dining reservation questions.


The sunrise peeking over some morning glory flowers with a Disney resort and palm trees in the background.

Early hours can be incredibly productive in the parks!  Being there for rope drop and getting to experience some of the most sought after attractions without a FastPass+ is great.  Especially when you can still use those FP+ later in the day. Getting up super early on vacation doesn’t always match-up with people’s desires. That’s ok too!

We can help you with plenty of strategies for maximizing your time in the park or relaxing, or a mix if you want.  One of our favorites is to actually alternate our days. Day 1, we may get up early to hit the park, return to our room for a rest in the afternoon, and then head back out for a late-night at the park. Day 2, we’ll sleep in, head out at our leisure, and then stay out until we’re ready to head back for the night. Day 3, repeat day 1. And so on, you get the idea. That seems to give us the best of both worlds. LOTS of fun, but without the burnout. This was especially effective when my son was younger (like age 4 or 5).

This is hardly a unique recommendation and could easily be covered in a Walt Disney World 101 course.  Yet, it is something that we still hear about and could be even higher on this list.


A young couple on Disney transit, a ferry or boat from park to park!

We covered this extensively in our Getting Around Disney article. We love the on-site transit and find it helps make our busy vacation a little bit more relaxing.  However, it isn’t without its headaches too. The buses seem to take some very perplexing routes on a schedule based on the same principles used to determine women’s clothing sizes (my wife could dedicate an entire website to her observations on that one!).  These observations and just from getting to parks from resorts, good luck if you’re trying to go resort to resort!

First-timers (or any logical human, for that matter) might assume that a more efficient system would be in Disney’s best interest.  Time lost in commute is time that is not spent doing any of the things that allow you to spend more money while there. Unfortunately, for reasons unknown, this does not seem to be the case. Transportation is not always efficient and it will take you longer than you expect to get anywhere. Just like morning traffic when you’re in a hurry.


Walt Disney World cards have Donald Duck and Goofy on them as a lady holds them to the camera

There are plenty of options when it comes to tickets and making them customizable to you.  This creates a double-edged sword situation. The downside is that without research, and possibly some experience, you risk paying for things you’re not going to use.  The upside is that with some research, and a bit of experience, you can really enjoy some extra magic with those add-ons!

This, of course, leads to a big dilemma for first-time visitors.  At the risk of sounding cliché at this point, that’s what we’re here for!

A great example is that on an extended trip, during warm months, the Park Hopper Plus option can really be beneficial.  Giving you access to the waterparks, in addition to the main theme parks and even some mini-golf time can be amazing changes of pace.  However, if you’re there for only 3 or 4 days in the middle of winter that option is unlikely to be used to its fullest on your trip.  There isn’t any true steadfast rule though. But, at least we can have the conversation and guide you to what makes sense for you.


Indiana Jones and a woman running away from fire

Alright, you probably saw this one coming.  Under-planning is a commonly cited diagnosis after a return home and relaying your story to friends or family that go frequently.  Although, we could question their loyalties if they go often and allowed you to go for your first time with barely any planning…  

Even if not yourself directly, if you’ve been a Disney fan long enough, you’ve heard from someone that returned home from their first trip and they had an awful time. With a few questions, you can usually see what happened.  Did they make Advance Dining Reservations? Nope. Have even a sense of how they’d like to approach the parks? Nope. Book FastPass+? Book what? Doesn’t that cost extra? You see how this is going.

You may lament the ‘death of spontaneity’ all you’d like when it comes to a Walt Disney World vacation.  To an extent, I agree and unfortunately, I don’t see a way back at this point. There are significant things you need to know before you go, which is precisely why we (Heyday Travel Company) and this blog exist.  However, I do visit non-Disney destinations, and no matter where you go there is an increased need for research and planning. Disney is hardly the only childhood destination, looking at you Niagara Falls, which has changed significantly and requires a new approach to visiting.



Yes, this seems in direct contrast.  Perhaps even odd that the trip “planner” is saying too much planning is bad.  The point is, find a balance that works for you. You can’t go in blind and expect everything to go the way you want on vacation.  Conversely, you can’t plan it down to the minute expecting everything to happen exactly as planned. Remember how I showed up to Legoland with my son on a day they were closed one time?

This is exactly why we like to discuss must-do items with clients.  There is always some amount of prioritization that needs to take place.  At worst, we’ll find you a way to get your must-do attractions in. Best, you hit all of your must-dos and a few of them ‘that could be fun too’ items. Approaching with some flexibility and reasonable expectations makes for a much better trip.


Jayme Mccolgan from unsplash shared an image of the Disney castle all lit up during a fireworks display.

Even with spending almost 30 days of 2019 in Walt Disney World, we didn’t do everything there!  There is just simply no way to do everything in a single trip. Even if you’re looking for an extended, once-in-a-lifetime vacation you’re not going to be able to do it all.  This is perhaps the single biggest mistake of first-timers and attempting this often leads to the kind of experience that causes people to never even consider another Disney vacation.

Bonus: Blindly Following Internet Lists!

So are you or are you not to follow these instructions?

Well, we believe that there is more than one right answer.  All of our suggestions here, as with all of our guides, are based on our experiences and opinions.  We offer them to others in the hope to improve their experience. We sincerely hope that you’re taking our comments along with your own research to make more informed decisions on your vacation.  If you read far enough you’ll find lists likely running counter to ours. While I personally avoid TriceraTop Spin, I also see people in line for it on every single trip that I take. In the end, it’s YOUR trip.

This about sums up our “top” first time mistakes for Walt Disney World.  This is by no means a comprehensive list of any and all mistakes that could be made… just some of the most common or perhaps most impactful ones we’ve experienced or heard of.  If you have any others, please don’t hesitate to comment or share by email. Your sharing, even of a “friend’s” experience, could help save someone else some heartache or a child’s tears.

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