Disney World Planning 101 (Part 1): The WHY, WHO, WHEN, and HOW

I will be the first to admit that I am, without a doubt, an all-out Disney fan. I love just about everything Disney, and nothing more so than Walt Disney World. I am lucky to have had the opportunity to experience Disney World at different stages of life: as an older kid (my first trip was in sixth grade); as a married, childless adult; as a parent with children back home; and most recently, as a parent with two young kids in tow. I am, by no means, an expert, but I do have one thing going for me: experience.

We recently returned from a week-long trip to celebrate my daughter’s fifth birthday. Even though I had been several times before this, I had never done much planning for those trips. But this time was different. This was the first time we’d be visiting Mickey Mouse with kids, and I knew that would make for a very different trip. I started planning our trip more than a year out! Is that a little overkill? Maybe. But I’m a planner and really enjoy the planning stages of a trip! In my year+ planning period I learned a lot, and thought I’d pass along some of what I learned to you, in case a trip to Disney World is in your future.

There can be so much to consider when planning a trip to Disney World so I’m breaking it down into three separate posts. This one will go into the WHY, WHO, WHEN, and HOW of planning your trip. The second part will look at the options of WHERE to stay, and the third will focus on WHAT you want to do.

Before I dive in, I want to point out that this series is not necessarily about how to do Disney cheaply. I share some money-saving tips, but that was not the main goal of our trip. Also, these tips are specific to Disney World, so some things may or may not work for Disneyland.

Okay, ready to get started?

The very first thing you’re going to want to do is go to the Disney website to create your My Disney Experience account, and download the same app onto your phone. This is where you’ll manage your trip, build your itinerary, and navigate through the parks.

WHY do you want to go?

When planning a Disney World vacation, spend some time thinking about WHY you want to go. Are you celebrating a birthday, anniversary, or wedding/honeymoon? Maybe you want to go just because it fits in your life right now and you think your kids are a good age. Taking the time to think about this will help you make other decisions down the road. If you’re celebrating a special anniversary milestone, you might be more willing to spend a little more for an experience that you might not otherwise want to do. Also, if you’re celebrating your child’s birthday, you might want to factor in his/her interests when deciding which parks to visit, attractions, character meals, and shows to see.

If you are celebrating something, make sure you stop at the guest relations locations at each park to pick up your free celebration button. Kids with birthday buttons, in particular, will be wished a happy birthday from just about every cast member they see (all Disney employees are called cast members). They may even score a few freebies! My daughter got a free cupcake at our character breakfast and a free frozen fruit bar at Hollywood Studios. And Gaston talked to her for about five minutes before moving on to the next person in line.

disney world planning tips

WHO will you take with?

Once you have a clear picture of WHY you want to go, decide WHO you want to include in your travel party. We invited both sets of grandparents and were glad to have the extra sets of hands and eyes. But keep in mind, the larger your party, the more difficult it can be to make Advanced Dining Reservations (ADRs) and FastPass+ (FP) reservations. Not to mention, there is a strong correlation between the size of your group and the speed at which your group can move around the parks.

For example, Hollywood Studios has two evening shows: Fantasmic and Star Wars: A Galactic Spectacular. Fantasmic starts at 9:00 pm and lasts approximately 22 minutes, and the Star Wars fireworks start at 9:30. If my husband and I had been traveling on our own, we probably could have made it to both. But there was no way we were going to get our group of eight from one to the other in time, so we had to choose one. (We chose Star Wars.)

Baby or no?

Are you wondering if you should bring the baby? While it’s a personal decision you’ll have to make, I usually encourage moms to bring the baby. Kids under the age of 3 get into all parks for free. They can also eat for free at buffet meals and can share a meal at all other Table Service (TS) and Quick Service (QS) meals. Each park has a fantastic baby care center where moms and dads can find a quiet, air conditioned place to feed, change, and rest with the baby. There are also some simple activities/toys to keep big brother and sister happy while baby eats!

We took our 16-month-old son who enjoyed pretty much everything, including warm naps in the stroller! Please note, any child whose feet may touch the ground, must wear shoes. If you’re little one is not yet walking, but is put on the ground to crawl, he/she must have shoes on. Some cast members are more particular about this rule than others. If nothing else, at least throw a pair of shoes in the diaper bag!

disney world planning tips

Another benefit to having extended family along is that you can share the cost of the Memory Maker add-on option. We split it three ways between us, my parents, and my in-laws. (More on Memory Maker later in Part Three!)

WHEN do you want to go?

Alright. You’ve figured out WHY you want to go and WHO will be going. Now you need to decide WHEN you want to go. The more flexible your schedule, the more likely you are to find a good deal saving you a little money. But, Disney almost always has some kind of deal to give out any time of year!

Holidays, school breaks, and summer are always more crowded than other times of the year. As are times when there is a festival or special event. That doesn’t mean you shouldn’t go at those times. In fact, Thanksgiving/Christmas time can be an incredibly magical time to go. It just means there will be longer lines for EVERYTHING: rides, ground transportation, dining, etc. If you have no choice but to go at one of these times, just be prepared for the crowds and longer waits. You’ll also want to make sure you take advantage of scheduling FastPasses at each park!

If you do have a flexible schedule, start with a crowd calendar to see which months tend to be less busy. Two of my favorite crowd calendars are:

Undercover Tourist:

This one very clearly shows you which park is recommended each day and how busy the parks are projected to be. You can view the calendar as a whole year to get a feel for which months are generally better, or you can view it month-by-month. It includes the park hours (which could change) and any festivals or special events taking place, as well as historical temp/weather data.

WDW Prep School:

This crowd calendar includes similar info as the Undercover Tourist one, but it also includes the dates at which you can start making ADRs and FP reservations which will come in very handy when you’re planning the WHAT portion of your trip!

Keep in mind the season in which you are planning to go. If you’re there when temps and humidity levels are high, you may not last as long in the parks each day, or you may end up moving slower and taking more breaks throughout the day. During the rainy season you may get rained out entirely (which is extremely rare) or just need to pause and take shelter to let storms blow past. Also, during storms, many of the outdoor rides shut down until the storm has passed, which is a bummer if you’ve already waited in line for a while. During cooler months, you might find the temps to be perfect for park hopping, but not warm enough to spend much time, if any, at the pool.

The other aspect to choosing when you’ll go, is how long you want to stay. A trip of any length can be a great trip! When deciding the length of your trip, take into consideration the number of people in your group and their ages. The older the kids, the longer they’ll last before getting burnt out! If you think this will be you’re one and only trip to Disney World and you want to see and do it all, you’ll want AT LEAST a week, if not longer. But your length of stay depends on WHAT you plan on doing, keeping in mind you will not be able to do it all in one trip.

HOW do you want to get there?

Next, you need to figure out HOW you want to get there, and HOW you want to get around while there.  


For people who live here in Iowa City, obviously the quickest way to get there is to fly. (If you don’t enjoy flying and think you can save money by driving, it’s about an eighteen-hour drive from Iowa City.) Allegiant Airlines has direct flights between the Cedar Rapids and Sanford airports and offers some great prices on flights. However, they have limited flight days/times and their pricing is ala carte (you’ll pay for everything, including carry-on bags, selecting your seat, etc.). It’s also important to know that Sanford is not the main Orlando airport and is located further away from the heart of Orlando and Disney World. If you are staying on-property and plan to make use of Disney’s free transportation from/to the airport, you’ll have to fly into the main Orlando airport.

If you’re willing and able, consider flying out from another airport. Des Moines and Moline are both relatively nearby. If you’re VERY willing and able, you can look further afield to Chicago, St. Louis, Minneapolis, or Milwaukee. My in-laws live in Madison, WI. Since they were going on the trip with us, we chose to fly together and found a great deal on Southwest out of Milwaukee.


If you’re staying on-property, you can get by without a vehicle if you plan to stay in the world of Disney. Disney has you covered on ground transportation for your entire trip. But, if you want to venture further afield (Sea World? The beach? Universal Studios?) you’ll like the freedom of having a vehicle. Plus, you can park for free at your resort and all parks. Depending on which resort you’re staying at, sometimes you can maximize your time by driving yourself to the parks, rather than waiting for a bus!


If you plan to drive yourself to the parks, there are a few things to keep in mind. Epcot, Hollywood Studios, and Animal Kingdom have their own parking lots at each park. Magic Kingdom is a little different. To visit Magic Kingdom, you’ll have to park at the Transportation and Ticket Center (TTC) and either take the Monorail or boat over to Magic Kingdom. The Monorail from the TTC to Magic Kingdom is a direct trip with some great views as you near the park. Many people, kids in particular, are excited to ride the Monorail, but don’t overlook the boat trip! The view from the boat is different from the Monorail and worth experiencing at least once!

disney world planning tips

You can also catch a Monorail to Epcot from the TTC, as well as hop on the Resort Monorail that goes between Magic Kingdom, The Contemporary, Polynesian, and Grand Floridian resorts.

Transportation Tip:

At the end of the day, when you’re leaving the park along with thousands of other people, and have to get back to your car parked at the TTC, you can either take the boat or the Monorail back. There are two Monorail lines in and out of Magic Kingdom: the Express Monorail that goes directly back to the TTC and the Resort Monorail that makes a loop through the three Monorail resorts AND the TTC. Most people, when leaving the park, head straight for the Express Monorail since they are not staying any of the Monorail resorts. The line for the Express Monorail gets LONG fast!

Do yourself a favor and hop on the Resort Monorail; the TTC is the second stop on the loop. Chances are you’ll be able to board the Monorail with little to no wait. Plus, you’ll get to ride through the Contemporary Resort, which is always fun!

If you’re staying on-property, you can park for free at all parks and at the TTC. But if you’re staying off-property, you’ll have to pay $20/day for standard parking, but that allows you to park at any and all parks for the day.

Hopefully this gets you started on planning a magical Disney World trip with your family! In Part Two I’ll go over the ins and outs of choosing WHERE to stay. Like I said, I spent a lot of waking hours researching and planning our trip. In that process I looked through more websites, blogs, discussion groups, and books than I care to admit. And I’ve found a handful of resources that I kept coming back to. Below are the resources that will help you the most and the ones that I liked the best. I’ve also included a short list of common abbreviations you might run into while planning your own trip.



Walt Disney World
WDW PrepSchool
Disney Tourist Blog
Undercover Tourist

Facebook Groups

NL Disney Moms
Smart Moms Planning Disney
Mom Approved Disney World Trip Planning Group


The Unofficial Guide to Walt Disney World with Kids 2017
Hidden Mickeys: A Field Guide to Walt Disney World’s Best Kept Secrets


My Disney Experience
Disney Store
Shop Disney Parks

Glossary of Terms and Abbreviations

7DWM: Seven Dwarfs Mine Train
ADR: Advanced Dining Reservation
AK: Animal Kingdom
BOG: Be Our Guest Restaurant
BTMRR: Big Thunder Mountain Railroad
CM: Cast Member
CRT: Cinderella’s Royal Table
DVA: Disney Vacation Account
EP: Epcot
FP: FastPass
HS: Hollywood Studios
MB: Magic Band
MDE: My Disney Experience
MK: Magic Kingdom
ROL: Rivers of Light
TTC: Transportation and Ticket Center


Becky is a Minnesota Native and Wisconsin Badger fan living in the heart of Hawkeye Country. Since graduating from high school, she has lived in Duluth, MN; Birmingham, UK; Minneapolis, MN; Louisville, KY; and Madison, WI, but is now happy to call Iowa City home. She and her husband have been married for ten years and have a spirited four-year-old daughter and a mischievous baby boy. Becky juggles working from home and keeping two kids happy each and every day. In her free time, she enjoys working her side business, spending time with friends, relaxing with a good book, and eating snacks.



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