Walt Disney World Trip Planning – Intro

It’s no secret that planning a Walt Disney World vacation takes A LOT of work. For most of us superfans it has become a fun part of the overall experience. For those who are new to Walt Disney World vacations or maybe just aren’t the planning type this is an extremely daunting part of the process. In this post I’m going to peel back to the covers on my trip planning process using my upcoming trip as a real world example.

It sounds cliche but I think it’s useful to break down the reasons for a trip using the tried and true, who, what, when, where, why, and how approach. At this point you’re probably rolling your eyes at my. I don’t blame you. Vacations are supposed to be fun! Why is this guy reminding me of elementary school lessons? Great question. In short, because I have issues and this stuff is fun to me. On a more serious note, it’s because the answers to these questions really do drive the planning process even if you don’t think of them so explicitly.


This is probably the easiest question to answer. For most of us it’s probably our immediate family. But the answer to this is really key. Your approach to planning and everything about the trip is going to be different if this is an adult’s only trip (Check out my Best Hotels for Adults post if this is you), or an extended family trip with elderly grandparents, or a trip with your partner and 3 kids. This will affect everything from where you stay and eat to how you tour the parks.


Whoa, whoa, whoa. It’s who, WHAT, not who, WHY. Well, I admit that who, what has a better rhythym to it, but I think answer the why question is THE single most important question to answer. This will dictate your priorities for the trip. If you’re going because you’re interested in trying every item at EPCOT’s Food and Wine Festival, then you need to plan accordingly. Conversely, if you’re looking for a relaxing and resort focused stay then that’s how you should approach every decision. I think the vast majority of people will say they’re going for a fun family vacation, or do get away from the cold (for those of us who live in the great white north), which is completely fine. The other questions will help you uncover the perfect trip. But if there is a special something type reason for your trip then respect that throughout the process. Don’t square peg, round hole it as they say.

Mickey and Minnie's Runaway Railway
Mickey and Minnie’s Runaway Railway


For some people this is no decision. Many folks only have the option to go when school is out, or when during slow periods at work. For others, Disney presents a myriad of interesting decisions for deciding when. If you have flexibility then think about what is most important to you. Do you prefer a certain kind of weather? Do you prefer less crowds? Do you like when the days are longer or when the parks light up earlier? Be honest with yourself about what matters most to you and your travelling party. There is no objective “best” time to go to Walt Disney World, just keep that in mind.

EPCOT Festival of the Arts
EPCOT Festival of the Arts


Walt Disney World, duh! Ok moving on…Not so fast. Where is not so easily answered. Walt Disney World has literally thousands of hotel rooms on site and there are many, many, more lodging options close by. By now you should have answered the why, who, and when questions. That’s going to give you a great idea of how you should answer this question. I personally always stay on-site because I love the Disney bubble and my travelling party allows maximum flexibility. But if you’re travelling with you and your extended family of 21 this question just got a lot trickier to answer. You know yourself and your travelling party. make sure you’re picking a lodging option that’s going to work for everyone. A disgruntled family is one of the quickest ways to ruin the magic!


For some people the logistics of the how can get very complicated. For most it’s fairly straightforward. Most people are going to fly from their local airport into Orlando International (MCO), pay for transportation to their resort, then do the reverse to go home. Others may rent a car, or if you’re only a few hours away you may just drive. For those flying in the biggest question is probably how to get to the resort from the airport. Since the downfall of Disney’s Magical Express, a loss I mourn to this day, we’ve exclusively done ride shares (Uber or Lift). With 2 people this is easiest and most direct. I’ve also considered the Magical Express Lite, aka the Mears Sunshine Flyer. The sunshine flyer is a good option for large groups or if you know you’ll be looking for a ride share at the most popular times (surge pricing is real!) For smaller groups, ride share is the way to go.

I can’t offer much advice about car rentals as we’ve never done that at Disney. MCO has a huge stable of car rental companies though, so your favorite is probably an option.


By the time we’re down to the last question there shouldn’t be too much left to answer on a high level. I look at this as a summary statement of all the reasons for this trip. “My Wife and I are going Walt Disney World for some time away during winter with a focus on the Festival of the Arts at EPCOT and to experience Tron for the first time. We’ll fly down on Southwest and take a Lyft to the resort.” Distilling everything down into one or two sentences helps me keep myself on track as I run through all the permutations. I still fall into the trap of over complicating the trip because of all the options available. Trust me, unless you KNOW you won’t ever be back to Walt Disney World, take a less is more approach and stick to your priorities.

In the next pieces of this series I’ll walk through a real world example using a trip that I have just booked and am still very much in the planning phases for. Meanwhile, let me know in the comments how you approach your Walt Disney World trip planning!

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