How to Plan a Trip To Disney World

Mar 21, 2019 | Family Travel | 0 comments

Disneyworld with kids

Planning a trip to Disney World?  But don’t know where to start?

Don’t worry – I’ve got you covered!

Welcome to my <simplified> (I hope!) “How to Plan a Trip to Disney World” Guide

Here are the bullet points.


Using sites like Undercover Tourist’s Crowd Calendar can be helpful. I prefer late January to late February.


It’s up to you to decide if and when your kids will enjoy Disney.  Alice (2.5) was free (bonus) but on the tad too young side.  George (nearly 5) was a perfect age.


If you ask me:  a Disney Resort.


Yes, this is true. But there are free travel agents who can help you.


We get as many days as we are there – minus one – with the Park Hopper option.


So you want to plan a trip to Disney World. 


I fully support this decision!

On a scale of 1-10 for Disney freaks I would put myself at a 7 or 8.   In 1992, I would have put myself at a 12.  My love for Disney is very very high.  But after our recent trip (and my recent research), I realize that my love is no match for the sheer obsession that is out there. 

I was looking around the Magic Kingdom on our last trip, and noticed so many . . . . interesting people. 

I mean true, hardcore, Disney devotees. 

Family Time at Disney World

There was a girl with badass tattoos all up and down her arms and legs – like dark, intricate tattoos – of Disney things.   If she wasn’t displaying her Disney love, I would never have placed her on the Disney spectrum.  I would have placed her at a severely hipster café giving attitude to customers and hiding behind her dye-black hair and huge glasses (I mean she probably is also this).  Anyways, I was surprised she was so into the mouse.

Then there was this ancient looking couple that looked as if they had stepped off Quadra Island (this is a BC reference.  Imagine the most hippie commune place where the staples are granola and weed and you will understand), with long gray hair, Birkenstocks, and necklaces FULL of Disney Pins (do you know the ones I mean?  Pin trading and collecting is BIG BUSINESS).

And in between were all the families in full on matching t-shirts or annual pass holders who proudly declared this on their hats.

Below all that is me. 

I mean my family was coordinated but we didn’t match. 

And I loooooooove Disney World/Land/Euro/Tokyo (yes, I have been to all of them numerous times). 

But I would never tattoo my body, devote every vacation or decorate my house with it.

Disney Kid

All of this is neither here nor there, I’m just setting the scene for my level of expertise (very little) and my love (pretty high) to help you plan your trip to Disney World.

Seriously, this trip meant so much to me.  I’ve been looking forward to it before I had kids. 

The idea of taking my unborn children to the happiest place on earth has been a dream for me.

Which I realize is a nightmare for others.

My knowledge is a drop in the bucket compared to all the information out there.  There are so many blogs out there that it is actually overwhelming. 

I’ve read many of them for months, did my own research, and then learnt my own lessons. 

And now I shall pass them off to you!

Disney World


When you start planning a trip to Disney World this is the biggest question of them all. 

So many factors to consider:  weather, school, crowds, holidays, and cost. 

Disney has made it even harder to figure this out. 

Back when I started going (circa 1988), it was a given that January and the first part of February were DEAD.  You could walk on Space Mountain without a line over and over again. This was true up until my last trip in 2012. 

I used Undercover Tourist’s CROWD CALENDAR to determine when we should go this year.

I opted for the green days of February 26, 27 and 28th with yellow days leading into March. I thought the crowds would be lower and the weather warm (in the past, my January trips have been rather chilly.  Like super chilly.  7 degrees in the morning!).

I was right about the weather (we got SUPER hot days which was a surprise) but wrong about the crowds. 

It was pretty busy.  It was the busiest I had ever experienced.

One thing I read about before we left was that these ‘dead’ times were a thing of the past.  Disney has made sure of this by adding fun festivals (Epcot Arts Festival in January and the Flower festival in March through to June), marathons (the Princess marathon happened before we got there), and free dining plans (usually something that occurs in August and September).  I thought ‘nah, we are good to go and I’m sure the crowds will be low’. Lies.  The crowds were high.  But as I had been checking the wait times on rides since January, it wasn’t better or worse than it had been in what used to be guaranteed dead time.  So the blogs are right.  There is no quiet time.

There are busy times, however.  If you want to avoid crowds:  avoid summer months like June and July, Christmas, or spring break (which starts in late February right through the end of March).

If I were to go again (which obviously I am already planning), I would aim for the last couple of weeks of January and the first two weeks of February.  Mostly because I can’t handle super hot weather and sort of want to check out Epcot’s Festival of the Arts. 

Or September.  Which I hear is STINKING hot BUT then my kids can play in the pool, the parks ARE quiet, and the dining plan is free with a resort stay.

Another instagram follower told me to go right after American Thanksgiving – and then you can see the holiday decorations!

The final time I heard was really neat was just over Halloween. You go for the Halloween party and on November 1st all the Christmas decor goes up.  So a 2 for 1 decoration deal for you dollar!

Family Time at Disney World

Look at my son’s face!  Doesn’t it just scream joy and enthusiasm?



Fair enough. 

This is something I hear a lot.

My reasons for taking our kids at the ages they are (2.5 and 4.5) were:

1.  Alice was FREEEEEEEE. 

Kids under 3 are free.  Free to the parks, free to eat, etc. and it is a huge savings. 

But is 2.5 a good age to take your child to Disney?  Sure!

Having a toddler with moods and the inability to be reasoned with was a tad difficult at times.

But more often than not, her little face full of wonder was too darn cute.

And she LOVED going on ‘JUMBO’ over and over again.

2. We wanted the kids to go when they still believed in the ‘magic’. 

Although my son already figured out that there is a man inside of Goofy (who told him? I am very mad at that person). 

George is still at that age when he unabashedly loves Buzz Lightyear, Mickey AND Snow White (without embarrassment for loving a princess.  Damn you school – I know what’s coming).

My first trip to Disney was at Alice’s age.  I don’t know if I remember it or not (you know when you’ve been told the stories so you can’t tell if your memories are real or just stories?). 

I do know that my mum still talks about how I took off when I saw Mickey and just stuck to him and Minnie like glue. I believed they were real.

My love and sentimentality for Disney was embedded then (which I realize might sound cheesy.  Disney was a safe haven for me when I was 11-13 during that awkward time between childhood and teens.  A time in which the mean girls were exceptionally mean to me).

I feel there is no perfect or wrong age. 

Kids at every age get different experiences.  I still believed in the magic when I was 13.  My mum is 73 and still loves the escape of real life you get at Disney.  

One thing I enjoyed at this age (with two children who don’t love rides) was slowing down to do the things I don’t normally do.  Like watching the Mickey and Minnie stage show, or parades, or a marching band or the Main Street singers.

This is something to think about when you are planning a trip to Disney World


Again, this is all my opinion so take it with a grain of salt.  And also please remember my husband is frugal frugal frugal.  Like FRUGAL.

And yet, we stay on resort property. 

This is our second time staying on resort property and I asked him what he would do next time and he once again said resort – no question. 

Staying on a resort property is significantly more expensive than staying off of property. 

I was very thorough in my research before we booked and priced out a MODERATE resort along with an Airbnb with car rental.  An Airbnb with car rental and day parking at the parks is about $1200 cheaper. 

We felt that the pros of paying an extra $1200 outweighed the cons of staying off property.

Hotel Disney

These last few paragraphs might confuse you if you have never been to Walt Disney World in Florida.

When planning a trip to Disney World you have to know:


Like crazy massive huge.

If you choose to stay ‘on property’ this does not necessarily mean you are across from the Magic Kingdom (I mean you can be – for about $600 USD a night), it just means you have easier and closer access to the parks than those who have to drive from outside the property lines.

We stayed at Disney’s Caribbean Beach Resort, currently a moderately priced resort (I say currently because as soon as the Skyliner Gondola opens up -I am sure the rates will go up.  No idea what a Skyliner Gondola is?  Check it out!).

According to Google Earth, we were literally across the street (and swamp) from the German and Italian pavilions at Epcot.  But you have no idea that you are so close.  The entrance to Epcot is still an uber/bus/gondola ride away.  

We chose it because we got a good deal on and it has a pirate theme that we knew our kids would love. 

We slept in pirate ship beds.  Not my first choice but the kids went bananas for them. 

The pool is very ‘Pirates of the Caribbean’ which the kids adored (check out the amazing splash pad!)

And the pool bar, Banana Cabana, has frosé so I was happy.

However, you can NOT take your drink into the pool (they why is it in a plastic cup Mickey?  WHY?).

When you go to plan a trip to Disney World where you stay makes your vacation more magical.

Advantages of staying at a resort:

1.  Free transportation to and from airport (see how I feel about this HERE) and free transportation to and from the parks.

2.  Access to the parks for their ‘Extra Magic Hours’  (or EMH) which occur either first thing in the morning or after closing.  I love this perk.  Although you can count on all 30, 000 (yes THIRTY THOUSAND) of the resort guests descending on the same park for the same perk, you van still walk onto Expedition Everest twice with no-line by 8:30 (although we were among the first at Hollywood and there was still a 90-minute wait for Slinky Dog!).

This might seem confusing. This first time we went, my husband said “aren’t all the hours magic hours?”


For example:  on Wednesdays the Magic Kingdom is open to everyone holding a ticket from 9AM to 8PM.  It continues to stay open, for only those staying in a Disney Resort, from 8PM to 10PM..

I cover early morning magic and after hours magic HERE.

3.  You are also able to book your restaurants reservations 180 days in advance which are called ADR’s  (this is 6 months folks – and it seems crazy – but you may need it) and your FastPass+ 60 days in advance (and this I definitely needed!).

4.  Another advantage might be the fact you are ‘still in the magic’. 

Disney resorts are just like anything Disney:  full of character, extremely happy staff members wanting to make sure you have the best experience possible, and lots of Mickey Mouse fun.

Take this as an example:  when I checked it, the man was so nice (shout out to Victor!) And got my in-laws in a closer room, spoke to my kids with a Donald Duck voice, and gave us about thirty Mickey Mouse stickers that the kids immediately plastered all over their pirate ship bed.  He then remembered my husband’s name the next morning and made sure we had a great first night.  On checking out, he cancelled (without penalty) my last reservation (which made me so sad – it was for a Snow White character dinner).  He remembered that we had checked in with him and hoped our stay was magical, etc.  Just little things, but just so in keeping with the brand of customer service.

Are these perks worth $1000-$1200?  We feel yes.  But this is truly a personal decision and a learning experience.

Disney kid


Yes, this is true.  More so than my trips to Disney World in the past.

So, if you like lots of planning and research like me then PLAN A TRIP TO Disney World!

If not – you can get a travel service to do it for you.  These two come highly recommended and are free (Disney pays them via commission):

Be Our Guest Vacations

Destinations to Travel 

But yes, it takes a ridiculous amount of planning ahead. 

I will get into more details in my next post but I did have to plan our days ahead of time which seemed frustrating. I mean how am I supposed to know what we want to do on February 27th at 2PM?  Do we WANT to be on the Slinky Dog Roller Coaster (which, by the way, I let my Fast Pass go for this one and never rode it!) Or do we want to be eating dinner at 4PM at Tusker House at Animal Kingdom? 

Travelling with young children and having to schedule so much seemed bananas.

I wanted to be carefree and go with the flow but if I had to be at the Magic Kingdom to get on Seven Dwarves Mine Train at 3PM on March 1st, how was this going to work?

We booked our trip less than 180 days in advance and no word of a lie, most of the restaurants were already booked! 

If that happens to you- as I learned – it’s not really a big deal (and I explain why in Part 2). 

UNLESS, you want a very early morning reservation or a reservation at Cinderella’s Castle.  This one definitely gets booked 6 months early and I did not see it come up once under cancellations. 

Disney kid

The other part that takes planning are your FastPass+.

What are FastPasses you ask?

A Fast Pass is a time window that you book (an hour with a grace period after they expire of 10 minutes) to get to the front of the line.


In some theme parks you can pay extra to have front of line access so people don’t believe they are free. But, yes, they are free.  And they only have so many per time so you truly are guaranteed to head to the front of the line (or near the front).

Choosing what rides to get them for and what times to get them for are a bit of an art.  Each person gets three per day per ONE park.  Once those three are used up, you are able to book another fast pass in whichever park you want.

In the Magic Kingdom, all rides and events are created equal and you can get a fast pass for Mine Train, Splash Mountain and Space Mountain (the big attractions).

At Epcot, Hollywood, and Animal Kingdom the rides are broken down into tiers.

Take Animal Kingdom:  all the Pandora rides are in Tier One.  You can only choose ONE ride in this tier.  You can choose three in Tier Two, or one in Tier One and two in Tier Two.

Confused yet?

It honestly makes sense once you get there, but it can seem confusing if you don’t know the lay of the land.

This is where your head might want to explode when it comes to planning.

What I did was this:

I cross-referenced the Crowd Calendar, my EMH (that Extra Magic Hours) timetable, and what parks we wanted to hit first and came up with a rough schedule.

Then I chose what rides were most important to us in each park.

Due to the fact we have small children, I opted for Peter Pan (yes, you need FastPass for this) and Enchanted Tales with Belle over Splash Mountain.  Or Frozen in Epcot over Test Track.  And Alien Swirling Saucers in Hollywood (fun fact-  my children liked NONE of these rides).  If your kids want to meet the characters – you can get FastPasses for all the meet and greets.

The rule of thumb is to get your FastPasses scheduled between 11 AM – 1 PM so that you can book other rides later in the day.

See? An easy-going trip.  Just kidding. It was not.

Having to rely on what Fast Passes were booked truly made us more regimented than I wanted to be.  When we finally got to Florida, figured out how our kids dealt with the heat, walking and waiting in line – I wanted to change plans!  But these damn FastPasses were set in stone.  And there isn’t much flexibility to change them.  We ended up going to Animal Park one more day than needed to go on a damn Pandora ride (the river one – honestly not worth it) and I gave up my coveted Slinky Dog FastPass because we were having so much fun at Magic Kingdom.  Alas – these are seriously first world problems.

Mouse Hacking has a very good post on this over HERE.

Disney Family


My choice is always as many days as we are there for and Park Hopper option.

These are a big expense – but obviously the biggest part of your trip.

We chose the 6-day pass for our 7-day trip because the price difference between 5 and 6 was not much.  We felt we could not go to a park one day and it wouldn’t be a total loss.

I also always pick the Park Hopper which definitely can add lots of money to your ticket cost.  However, after more research I found that if you are going for a longer time (like we did), the Park Hopper was only an additional $75 for all of us. Not bad.  But if you are going for a shorter period of time, the Park Hopper can add quite a lot to your ticket.  Which sort of sucks because that’s probably when you would want one.

Epcot Monorail

Oh, what’s a Park Hopper you ask?

That means you can go to any of the parks on any given day.  All four if you wanted.

If you don’t have a Park Hopper that means if you go to Magic Kingdom on a Monday, you can only do Magic Kingdom that day.

If you have a Park Hopper, you can go to the Magic Kingdom Monday morning, hop over to Epcot Monday afternoon, and end up at Hollywood Monday night.

Additionally you can add the water parks to your park ticket.  We did not do this this time but I can assure you the water parks are A-M-A-Z-I-N-G.

Don’t freak out if you just get the base ticket and change your mind when you get there – you can upgrade anytime for the same price as it would have been at home (urm, this I might have to check on.  Canadian residents get a ‘deal’ so it might be a tad more).

Okay, I feel this is a good amount of information to get you started.  For reference here are the blogs I used before planning our trip:


I stumbled upon AJ on Youtube somehow and got addicted.  I watched all of her vlogs and wrote down all of the food she told me to eat.  This was one of my favourites.


I found this one super helpful for honest, helpful and easily-laid out planning information.  Tom Bricker says when things are good and bad – which I appreciate.


This is another great one for honest, helpful planning.  It’s written by a dad, Carl Trent, who goes to WDW all the time and knows his stuff. I enjoy how nerdy he is about Disney!


I love her food and drink ideas and her pictures are great.

Coming up next with my Disney adventures:  what worked, what didn’t, what I learned and why it was an amazing vacation for my family.

Happy Adventures,

Curious in Wonderland

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© 2021 Curious in Wonderland