Six Steps to Planning a Walt Disney World Vacation: T’s Breakdown

Knowing me (~T~) means that you know I have quite an affinity for Walt Disney World!  It is no secret to my friends and family and I take no shame in my infatuation.  Over the last few months, I’ve actually had some tremendous chat sessions with many of my friends about vacationing at Walt Disney World Resort (WDW) in Orlando, Florida.  While many of my cronies have been down there already and many times, I  know some who are still dreaming of meeting the Mouse for the very first time.  Among those who have never been, there is a good handful who have expressed to me how overwhelmed they are with even the thought of planning this kind of a trip.  There are too many choices to make, too many things to see, too many expenses for which to plan! A few of them have even shied away from going on a WDW vacation because of the immense amount of planning they fear goes into it, which could, of course, potentially and ultimately become a negative part of the process. Well, let me speak from experience.  Yes – it can be overwhelming.  It can be daunting.  However – it can also be contagious, exciting, eye-opening and magical!

Our family has been vacationing at Walt Disney World since 2007. If you know anything about our family, finding a safe vacation spot has been difficult over the years as we have a little guy who struggles with severe, life-threatening food allergies.  Because of the care and dedication Disney chefs have demonstrated towards our family (and countless others), we have found ourselves our home way from home in WDW.  This has afforded me the opportunity to spend many hours planning our at least annual trips and I recently came to notice that I have somewhat of a system that tends to take the sting out of the burden, the exhaustion out of the process for me.

I’ve noticed that, in planning our trips to Walt Disney World, there are six major areas of decisions that need to be addressed: dates, transportation, accommodations, dining, Theme Parks and FastPass+ selection.  I tend to carve out a little time each day to spend solely working out the details of each section and find that my trip is planned in no time.  Let’s see if we can make this work for you. I’m going to encourage you to grab about six to eight pieces of paper. Go ahead – I’ll wait…Oh, don’t forget a pencil!   Some people (like me) even like to grab a three ring binder and start a whole planner on this sort of thing, but there is no pressure to do so.  Okay, now label at least one sheet each with the section titles listed above. Below, I’m going to try to share with you step-by-step the order in which I personally break the planning down.  You can use the paper to doodle your own ideas, scratch down things to keep in mind, etc.  I am going to be as basic as I can to avoid overwhelming you, but there is still a lot of ground to cover.  In the future, I plan to flesh out these six sections in dedicated blog posts in order to provide a more detailed look at planning a WDW vacation.

Dates: Okay – first things first.  You need to determine when you are planning to take this magical trip.  Take out your calendar and the first piece of paper labeled “Dates.”  Figure out when you are going to vacation and the length of your stay.  Be sure to take school vacations, upcoming business meetings, family events and travel-time into account.   Now jot down a few options, weighing out the pros and cons as to why this would be a good time to visit Florida.   Some of the questions you can ask yourself are as follows:

  1. Is there a time of the year you have to go on vacation or can you be flexible?  Some companies require their employees to schedule their time-off during certain times of the year.  Teachers usually have less-than-flexible times they can vacation during the school year and, believe it or not, there are some kids who don’t like to miss school (I, oddly enough, have three of those very strange and unusual children).
  2. Is there a particular season or month of the year that you have been dreaming of visiting WDW?   Some like to visit in the summer and others during the Christmas holidays.  WDW also hosts many special events throughout the year that tend to attract Guests, such as the Epcot International Flower & Garden Festival, the Epcot International Food & Wine Festival,  Mickey’s Not So Scary Halloween Party and Mickey’s Very Merry Christmas Party.  
  3. Do crowd levels matter when you plan on visiting the Resort? Florida schools  are in session August to May and we usually love to go at the very end of August when the crowds are fairly low. There are months during the year when it is nearly wall-to-wall Guest (and stroller brigades), while there are other months where you can ride an attraction several times before noon!

TIP: There are many websites that have crowd calendars, which can be very useful tools when it comes to planning out your trip.  I encourage you to do some research on which one(s) makes the most sense to you.

Transportation: Go ahead and grab the sheet that you have labeled, “Transportation.”  Here is where you decide whether you are going to fly, take a train or travel down in your personally-owned vehicle. This may be the easiest of all decisions to make.

  1. Which will be more cost-effective for your family?  Do your research!  Compare costs of airline tickets, check gas prices, take weather conditions during that time of the year into consideration, et cetera.
  2. Which would be the lesser of three evils? It’s important to get there  and home with as many brain cells intact as possible.
  3. Which one will test your sanity less?  See above.

When we travel down as a family, we go down in our own mini-van because I am not quite there yet when it comes to trusting airlines with our son’s food allergies.  Our three boys actually love the long drive! Yes, I know – what strange and unusual children I have.   Now, when I go down by myself or with one other family member, we do tend to fly because getting there as soon as possible becomes the magical priority.

TIP: If you do fly and plan on staying at a Walt Disney World Resort hotel, you have the added perk of using the Disney’s Magical Express to get you to and from the airport.  I LOVE this bus trip from the airport….not so much the trip back to the airport (at which point many of us change its name to the Tragical Express).

Accommodations: It’s time to find the sheet you have labeled, “Accommodations.”  This one may take up both the front and back of the sheet you are using next.  Here is where you decide where you are going to spend your off time when not enjoying the Theme Parks or Disney Springs.

Disney's Grand Floridian Resort & Spa ~ photo taken by T.M. Brown
Disney’s Grand Floridian Resort & Spa ~ photo taken by T.M. Brown
Disney's Pop Century Resort ~ photo taken by T.M. Brown
Disney’s Pop Century Resort ~ photo taken by T.M. Brown






  1. The first question to ask yourself is: Are we going to stay on or off the Resort?  Some people think they can get a better deal off the Resort, while others feel that staying on provides them with more perks and the all-inclusive feeling of being on a WDW vacation. We have done both and I would rather stay on the property and be as close as I can to the action.  Staying in a Walt Disney World Resort hotel also provides you various methods of free transportation to and from the Parks and Disney Springs, the added plus of Extra Magic Hours and the accessibility to Cast Member assistance 24/7.
  2. Should you decide to stay on the WDW Resort, what type of accommodations should you choose?  This is where you ask yourself, “Am I going for cost-effective, simple comfort or going all out because, heck, we’re on vacation?!”   It’s important here to also know what your family’s needs are with regard to space. WDW offers numerous themed value, moderate and deluxe resort accommodations, making sure there is something for everyone.  We have stayed in all three styles of accommodations and, though we have our favorites, we have enjoyed every single one of our many resort stays.

Theme Park Tickets:  Normally, our family would begin to plan out our dining itinerary at this point.  However, as this may be the first time you are taking on this adventure, it may be more beneficial to decide on your park plan first.   There are four main Theme Parks and two Water Parks, for which tickets are required.   There are also many available ticket options from single day tickets, multi-day tickets, Park Hopper tickets and tickets that come with packages to military discount tickets and the coveted annual passes.  The point is not to stress out about these. Just talk yourself through this step, keeping the next few thoughts in mind, before committing.  The website has a page that allows you to play around with pricing, as well.

  1. Based on your vacation time, how many days do you plan to spend in any or all of the Theme Parks?  Speaking from experience, I would highly recommend spending a day at your Resort or at Disney Springs (which has been growing over the last year or so and is a wonderful place to spend some “free” time).  That day off may very well be the decision that becomes the salvation of your trip.
  2. From there, you can determine if you would like to add on the Park Hopper option to your tickets.  This enables you to visit more than one of the Theme Parks in the time frame of one operating day. This is particularly helpful if you plan to spend the morning in one park and have dining reservations in another.  I’m not so sure I’d recommend it for those with little ones.  Just my own two cents.
  3. There is also an option that allows you to purchase an add-on that grants entrance into the two Water Parks on the Resort property.  I admit, I have not been to either of the Water Parks as of yet.  I can’t get myself to feel comfortable enough since Logan has to carry around an Epi-Pen everywhere.   BUT – this may be high on your list of must-do things for your vacation, so be sure to check it out on-line!
  4. We will leave the details of an annual pass to the more dedicated blog post coming in the future.  If this is your first trip, it is probably not going to be the first ticket you purchase and there is always the option of upgrading your pass at Guest Services if you decide this would be a good choice for you.

Dining: Okay – you are definitely going to need two sheets for this section!    Here is where you are going to decide your family’s dining plan for your vacation.   Knowing your family’s eating habits is a must here as you don’t want to over-plan your dining experiences.   This is actually our favorite part of the planning process!  With a household of growing boys, the Disney Dining experience must be just that – an experience and Disney offers many!!!   We spend most of our planning time on this section because we like to glean through the list of dining options on the website and create our list of musts for our next trip.    Before we move forward, it is important to note a few things. Some restaurants are in the Parks, some are at Resort hotels and others are at Disney Springs.   The website (and smartphone app  – to be discussed at a later date) offers you the opportunity to select a location (Park, Resort hotel, Boardwalk or Disney Springs) to help you find the appropriate dining options available.   Please take note that table service dining locations found inside the Parks do require that you have paid Park entrance, so plan these out accordingly.   Questions that you will need to ask yourself while planning out this part of your vacation would include the following:

Dinner at Grand Floridian Cafe ~ photo taken by T.M. Brown
Dinner at Grand Floridian Cafe ~ photo taken by T.M. Brown
Captain Cook's at Disney's Polynesian Resort ~ photo taken by T.M. Brown
Captain Cook’s at Disney’s Polynesian Resort ~ photo taken by T.M. Brown






  1. What type of dining experiences are you looking to have?  Are you interested in all table service, quick service, snack-style foods or a healthy combination of the three?  When choosing table service, there are buffets, family style service, character meals and regular sit-down table service. The quick service (or counter-service) option allows you to just wing-it time-wise and do eating when you are ready without reservations.  There is also a plethora of opportunities to grab a small bite or two on the fly and Walt Disney World has some of the BEST snacks!  For our family, we tend to eat breakfast in the room most trips, snag a table service for lunch and then eat on the go at a quick service for dinner when we finally get hungry again.
  2. What kind of dining experience are you looking to have? For instance, if character dining is high on your list of priorities, these are some of the experiences that fill up quickly.  There are many options here, so determine what characters are the family favorites and I would recommend you find those first.
  3. Does purchasing any of the various Disney Dining plans offer you any added benefit?  This also depends upon your family’s eating habits and takes a little bit of mathematical thinking to figure out.  Some people just find it so much easier to purchase one of these because they know what they are allowed and don’t have to worry about cost (except gratuity, which is not included).  NOTE: I did try to link the page explaining the dining plans, but there were some technical difficulties when trying to do so.

TIP: Here’s a great tidbit of information to keep in  mind when it comes to making advanced dining reservations (ADRs).  Guests can make their ADRs up to 180 days prior to their first day of arrival.    I have an entire post dedicated to this coming in the near future, as well.

EXTRA TIP: If anyone in your family has food allergies, Walt Disney World does not want you to worry!  Their Disney chefs have the training, knowledge and expertise needed to serve an allergen-safe meal to accommodate most, if not all, situations!   Keep an eye out for my piece regarding our experiences with Disney Chefs in the near future!

FastPass selections: This will likely be one of the last major decisions you have to make with regard to your fundamental pre-trip planning sessions (minus packing, of course).  There are some attractions that draw the crowds and tend to develop very lengthy wait times in the queues.   In the past, WDW offered paper FastPasses at the attractions themselves that provided Guests with a one hour window in which to return to the ride for a quicker entrance.  Around 2012/2013, WDW updated the system and created the FastPass+ system, which enables Guests to pre-select and schedule on-line up to 60 days prior to their vacation and up to three attractions in a Park for each day of their visit (to include shows, events and character meet-and-greets). Once those three FastPasses are complete, you have the option to add more for that particular day.  Now, some have found this a spontaneity-killer.  We have actually found it liberating! I’m going to elaborate more about the FastPass+ options in a future post because there are some tips I’d like to offer that have worked for us…but I did have every intention of keeping this particular post brief (I really did!).

And there here you have it – the six fundamental parts to planning a Walt Disney World vacation… my own personal opinion, of course.   I wanted to at least create a sense of “do-ability,” as well as find a somewhat simple way to help people organize their thoughts and begin the planning process for a vacation like this.  I’m not a travel agent, nor do I want to become one.  In fact, if you still find this overwhelming, there are tons of wonderful Disney-certified travel agent out there to help you plan your trip, as well as Cast Members on the website ready and available for questions.  Another tremendous resource for magical answers is the Disney Parks Moms Panel.  Of course, I’m always open to questions, as well, so please feel free to drop a note below.

Stay tuned as I plan to flesh out the above sections and offer added tips and ideas on how to work out your own Walt Disney World vacation plans!!!   If you have a system, I’d love to hear it!  How do YOU plan a magical vacation to see the Mouse!

Until the next step ~ T

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