I Finally Understand Why They Called me Crazy! (Walt Disney World Vacation Post)

Disney World

For the past 15 or so years, whenever the topics of vacations would come up, I would always tell everyone that my favorite and absolute most stress free vacation was a Walt Disney World vacation…

…and without fail, EVERYONE would look at me like I was crazy. Some even called me crazy to my face! They said it was stressful, impossible to plan, blah blah blah. Yes it was fun, but that it was not stress free at all. But to me, it was the easiest vacation ever!

Well…now I’m planning a trip for this year, and I finally understand why they feel this way.

In the past, whenever we’ve gone to Disney World, it was a given that we’d stay on property. After all, that was the only thing we were doing the whole trip, except for a day at Universal Studios or Seaworld (we’d usually go to one of the two each trip.)

We’d take Magical Express (a free service from Disney that takes you from the airport to your hotel, and even takes your luggage from the airport and puts it in your room!) stay at Disney the whole time on property, get the dining plan for free (they often offer it for free in August/September) and it wasn’t crowded so we didn’t wait long for rides either! Then we’d take Magical Express back to the airport, and not see our luggage from when we gave it to them at the hotel until we landed back at home!

It was seriously the most relaxing vacation ever! Yes, we did a lot of running around at the parks, and it’s not a “sit at the beach” type of vacation, but to it us it was completely stress free and relaxing…and a lot of fun!

Well…we went to Disney World last year with the whole family. We weren’t planning on going back until next year, but we just decided we wanted to take another trip to Florida. We usually spend the entire time at Disney, so this time, we decided we’d spend part of the time at Disney, part of the time doing other things in Orlando, and then part of the trip in Tampa since we had never been there before.

THIS is when I finally realized that if you don’t know EXACTLY what you want to do for your Disney trip, it can be stressful and overwhelming.

I’m going to break this up into separate posts, because really, there can be a lot to get stressed out about when it comes to planning and booking a Disney World vacation.  I’ll also share how I solved the problems…and even though I’m nowhere near done planning, at least the overwhelm is gone, and so is all of the stress!

Starting with my biggest cause of stress…


I started looking at hotels that were close to Disney, and offered shuttles to the parks. Then I started finding out that some hotels make you pay for parking (we’re renting a car because of all of the different things we’re doing – something we haven’t done before in Orlando.) It also turns out that a lot of the hotels have resort fees of $30 added onto the total…and so on.

I thought it was going to end up being a lot cheaper to stay off property, and it turned out that wasn’t the case. But I spent a lot of time searching all of the hotels, and there are so many that it was stressful, and definitely not part of the fun. Do you have any idea how many hotels there are in Orlando? Oh my goodness. Even just pick one chain and there are multiple hotels all in the same area! It did not make things easy.

I was hoping to find a hotel that was walkable to Disney Springs, so that we could take a free shuttle to the parks in the morning, and be able to walk back from Disney Springs if we wanted to at night, that way we wouldn’t be totally dependent on the shuttles.

But then I kept reading about how the shuttles don’t come that often, and stop at many other hotels, so it takes a while to get there and back. So even if your hotel participates in early morning hours, by the time you get to a park, that time is over and the park is open to everyone.

After going back and forth between so many different hotels, and realizing what the final price would be after the parking fee and resort fee, I decided maybe I should check out the price of staying on property. It turns out that the prices were very similar, so we decided to just stay on property at a value resort.

Here’s where our next problem came up. Normally I plan the Disney trip out months and months in advance. We recently made the decision, and it wasn’t that long until the trip. So now there don’t seem to be many rooms left in the value resorts. I wanted a standard room in a value resort (preferably Pop Century, but I’d take an All-Star if that wasn’t available.) When I first started looking but wasn’t sure I wanted to stay on property, I saw a room at All-Star Music. Just a few days later though, there were no more rooms available.

I ended up changing the week we we were going to go, just to find a time that had a value resort available. Of course I took into account the crowd levels too. I don’t want to go when it’s crowded or when school’s out.

So the second I found a date that had a value resort available, I booked it!

That was a lot of the stress.  I now understand what other people are talking about when they say that it’s not a relaxing trip, and that it caused them a lot of stress.  And I’m not done with the planning at all.  Now I have to book restaurants, FastPass+, airfare, rent a car, and more. But most of that is a lot of fun to me…not stressful.

But I totally understand where other people are coming from now!

Before I list out what other issues I had, and how I solved them (or am in the process of solving them), I want to share how I ended up saving money on my Walt Disney World Hotel. Usually, I book right through the Disney World website. This time, I went through Undercover Tourist. I was able to choose the type of room I wanted just like on the Disney site, and the best part was the price was less! I ended up saving about $100 by booking through their site instead. And as soon as I booked it, I was able to enter my confirmation number into the Disney website and could see my hotel reservations perfectly. Now I can book everything else myself on their website, such as my dining reservations, FastPass+, and even customize my magicband, which I’ll get for free because I’m staying at a Disney hotel.

What comes next? Airfare (post coming soon!)

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