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9 Critical Steps When Planning a Disney World Trip

There’s no question that planning a trip to Walt Disney World can be overwhelming!  And honestly, it’s only gotten worse now that everything is being done digitally, the crowds have gotten larger (there is seriously NO slow season anymore), it’s becoming super expensive, plus you have to factor in changes post-COVID-19.

Planning ahead and being strategic about your vacation can mean the difference between paying an arm and a leg or having a ‘reasonably’ priced trip – by Disney standards at least. LOL

I want to walk you through some of the basics for planning a Disney World trip. You’ll definitely want to keep all of these in mind BEFORE you leave for your vacation. Forgetting one critical step could derail your trip or cost you a lot more money and I’ve read too many unfortunate stories of that happening recently.  Breaks my heart!

Picking Dates

Like I mentioned above, there is really no ‘slow season’ at Disney World anymore.  They used to have sales during ‘value season’ way back when I was young, and that was typically when my family would go.  An example of this was usually early October through mid-November.  But now, you have the Food & Wine Festival at Epcot, Mickey’s Not-So-Scary Halloween Party (pre-COVID and hoping to return in fall of 2022) at Magic Kingdom, etc.  Disney basically created events to drive in guests during those ‘slow periods.’

So what does this mean for you?  When planning a Disney trip, I think you should start with what works best for your family and your schedule.  Yes, you can go during ‘slower times’ – like early-mid November is still going to be LESS busy than the summer – and that will help, but you need to make sure this trip works for your family’s schedule.

Reservation System

Once you’ve decided on some possible dates, you need to go look at Disney’s Theme Park Reservation system.  Disney World implemented this system when they reopened after the initial start of the COVID-19 pandemic.  I’m not really a fan – I miss the old days of just waking up and saying ‘let’s go to this park today’ – but it doesn’t sound like this system is going anywhere any time soon.

**YOU MUST PURCHASE A PARK TICKET AND RESERVE A PARK TO BE ABLE TO ENTER A PARK ON A GIVEN DAY.**

Transportation & Rentals

You may or may not already know, but starting January 2022, Disney is no longer running it’s Magical Express from Orlando International Airport (MCO) to it’s resorts.  This was ‘free’ (ie included in everything you’ve already paid for HAHA) if you were staying on Disney property.

Even when Magical Express existed, we still used Tiffany Towncar in the past.  I love that they meet you inside by baggage claim, help you load up, have car seats available if you need them, and allow you to make a 30 minute stop at Publix on the way to your hotel (at no extra cost).

*Publix is an amazing grocery store if you’ve never experienced it.  We had it when we lived in Auburn & Atlanta and we miss it SO much!

No need to worry about this if you’re driving.  And don’t let driving with little kids scare you.  You can check out our posts about taking a road trip with a baby or toddler and packing for a family road trip.

You can also rent a car.  That’s a really expensive option right now during COVID times, but it is totally nice to have your own set of wheels to come and go as you please.  Do know that Disney Resorts do charge for on-site overnight parking (different rates depending on level of hotel), but you don’t have to pay to park when you go to the theme parks.

We also highly recommend booking a stroller rental if you’re flying!  It was a total game changer for us to have one less thing to worry about while juggling all these kids.  We’ve used Kingdom Strollers the last 3 times and have had great experiences with both hotel delivery and airport pickup.

Weather Considerations

We live in New Orleans, LA which has pretty similar weather to Orlando.  We’re used to the heat & humidity and rapidly changing weather situations.  If you live up north, Orlando is going to be tough for you in the height of summer.  We think it’s miserable and we’re super used to that weather!  South Florida (okay the entire deep south LOL) is known for random showers during the summer months.  You might be happy for the cool off, but consider your footwear strategically and carry ponchos.

If you’re going during the ‘winter’ months – say December through mid-March – the weather can really swing in different directions.  I mean SWING y’all – one day it’s 37 degrees when you wake up and 2 days later, the high is 75 degrees.  You have to be super strategic about how you pack clothing-wise and what you choose to bring with you to the parks each day.  Hint: Layers are key!

Lodging

On property or off property?  That is the question!

We’ve done both.  Growing up, my family always stayed on property (Port Orleans for life y’all), but we were a family of 4 and things were definitely much cheaper back then.  I LOVE staying on property because you are truly immersed in everything Disney.  Everything is MAGICAL.  You can’t replicate this feeling off property.

With that being said, we are a family of 5 – soon to be 6 – and the standard hotel rooms don’t fit us and we are just not paying for 2 rooms.  

This was one of the main reasons we decided to become DVC members (through the resale market).  I really wanted to be back on property, but we needed to find a cost effective way to do it.  And you don’t need to be DVC members to stay in a DVC room.  You can buy rental points from DVC members not using theirs for the current year.  When I’ve run the numbers, you can definitely rent points cheaper than paying cash for a hotel room (and you get more space!).

We’ve stayed at the Hilton Grand Vacations properties a few times when my parents had extra points, and those are great properties as well.  

Many folks stay at AirBNBs in the Orlando area, especially if they’re not just doing Disney (there’s Universal Studios plus tons of other Orlando attractions).  Make sure to grab one with a pool if you’re going between May-October!

The My Disney Experience (MDE) App

You’ll do everything through My Disney Experience, and you’ll definitely want to download the app on your phone.  You’ll be able to see all of your Disney reservations here and make any changes you need/want to.  You can use the app for your hotel (if staying on property), park tickets, to order for Mobile Orders at quick service dining locations, looking at all restaurant menus ahead of time, checking ride wait times, directions around the parks and you can even use it to pay for purchases on property.

Dining

You can make dining reservations 60 days from your first park reservation or check-in date if staying on property.  Dining has been even harder to come by since the COVID-19 pandemic.  It’s a variety of causes, but just know that you need to be ready to hop on the morning of that 60 day mark and grab what you can.  Have your ‘top choices’ and ‘backup choices’ ready to go.  Know which parks you’ll be at, so you can be strategic about your choices.  Mouse Dining alerts are a great alternative.  We’ve always had plenty enough options with the free plan; no need to pay!  

In the 3 times we’ve visited since COVID, we’ve done more quick service and less sit down restaurants.  We’ve also driven there, so we have our car and choose to eat dinner off property at a local restaurant or back at the condo (can’t ever go wrong with picking up some pizza on your way back!).  Magic Kingdom always tends to be our longest day, so dining for us looks like this: breakfast at the condo, bring lunch with us, eat dinner at the parks using a quick service order.

COVID-19

As of the date of this blog post, masks are required at all indoor locations for guests ages 2 & up regardless of vaccination status – this includes indoor ride queues, busses, monorails, skyliner and stores at Disney Springs.  Disney is strict on this, so make sure your little one can handle this.  Unlike on an airplane where you can sometimes get by with letting them ‘eat’ the entire flight, this will not work in Disney.  Unless you are actively sitting at a table dining, masks on!

Disability Access Service (DAS) Pass

This has been a God-send for us for Hunter!  We didn’t learn about it until about his fourth or fifth visit.  A sweet cast member happened to mention it to us one day when she saw we were struggling.  Per the Disney website: “DAS is intended for guests who have difficulty tolerating extended waits in a conventional queue environment due to a disability.” 

Basically, you ‘wait’ for a ride by getting a return time equal to the current wait time BUT you don’t actually do the waiting in line.  This has been so helpful as Hunter does not like being trapped, loud sounds, or people invading his space.  The meltdowns are hard to contain once they get started, and being stuck in a queue possibly unable to get out only perpetuates the situation.

With some new rollouts, you can now choose your ride selections through the MDE app.  It was BRAND NEW when we went last November, and y’all – it was a GAME CHANGER.  No more running across the park to scan for the next ride!

Included in those new rollouts, Disney now also offers the option to pre-register for the pass 2-30 days prior to your trip.  If you don’t want to pre-register online, you can simply go to Guest Relations on your first park day.  This is how we’ve done in the past and we had no issues; but we’ll be trying out this new system very soon once we are inside of our 30 day window for our upcoming 2022 trip (I’ll make sure to report back!).  Pre-registering not only eliminates the need to wait at Guest Relations on your first park day, but it also allows you to make 2 advance selections.

*Please note that the DAS Pass is NOT for mobility disabilities.  The Disney queues have all been adapted to accommodate wheelchairs and scooters.

Resources Mentioned:

33 Must-Know Tips and Tricks for Disney

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I'm Kimberly

and this is where it all began

As a wife, mom, and business owner, I started this blog as a passion project to share all the things I’ve learned throughout my journey.

To say it’s been a crazy ride would be the understatement of the century, but we have loved sharing our adventures every step of the way.

That’s why I always come back to where it started – this very blog – to continue sharing my tips, tricks, triumphs, and tribulations about all things motherhood, money, business, traveling, and everything in between.

I hope that by sharing these authentic, unfiltered experiences, you can feel seen and heard and learn to embrace the wonder in this messy (but oh, so wonderful) life.

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33 Must Know Tips & Tricks for Disney World

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