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Planning a Trip to Disney World: Before You Go

Last fall the four of us (two adults, a 2.5  year old, and a 9 month old) packed up the car and took a little road trip down to the “Happiest Place on Earth.” Since we were pretty sure we’d be moving sometime in 2016 (we were right), we wanted to take advantage of planning a trip to Disney World while it was within driving distance. I’m SO happy we visited Orlando when we did. We were there in the middle of November, so the weather was fantastic, and it wasn’t horribly crowded.

I’m going to break our trip up into a few posts, just so you don’t have to read a novel all at once. There are a lot of components that have to happen when you’re planning a trip to Disney World, so hopefully some this will help some of you.

Planning a trip to Disney World and what you need to know before you go


Before You Go—Hire a Pro:

So here’s the thing: there are one billion blogs and websites out there specifically for planning a trip to Disney World. Seriously, I’m pretty positive I’m not exaggerating about that number. When I first started planning our trip it was enough to make my head spin around faster than the tea cups ride at Magic Kingdom—and that’s saying something since I actually love planning vacations. The thing is, planning a trip to Disney World is unlike anything I’ve ever experienced before, because there are so many options, and so many different things you need to do ahead of time. A few days into planning everything I essentially freaked out and just stopped cold turkey, because there was just way too much to handle.

Enter: Road Less Traveled Vacations with my friend Casey. (I promise this isn’t a sponsored post—she doesn’t even know I’m writing about her; I just love what she does and need to share it with you.) Casey is a travel guru, knows about all things Disney World, and since her services are free if you end up booking with her, I decided to give her a shot, and I’m incredibly happy I did. (That’s right, I said Disney World and FREE in the same sentence.)

[Tweet “If you’re planning a trip to #DisneyWorld, save yourself the trouble and hire a pro!”]

I told her what we wanted to do (visit DW) and that my head was spinning with figuring out what to do and how much it would cost. She gave me a little pep talk that included something like, “Jess. Don’t worry about a thing. Planning a trip to Disney World is bonkers. I’ll take care of it all for you.” Consider me sold. I gave her tentative dates, what we wanted as far as going to the parks, and what kind of room we wanted, and she filled me in on the rest. When I got overwhelmed thinking about all the dining options and package options, she broke things down for me, and worked with our budget. Having her break it down for me was a gigantic a sanity saver.

We started planning for the trip six months before we actually left, and honestly, I felt like we were already a little behind at that point. Planning a trip to Disney World is no joke. Road Less Traveled Vacations helped with every single step along the way, and she answered every question I had without ever making it seem like I was a bother (which I’m sure I was, many, many times with how many questions I had)! She helped make our dining reservations, gave suggestions on where to eat, and what to do—especially as far as Fast Passes were concerned, and before our trip she even sent a little package to my daughter with some princess stickers and some “first visit” buttons.

When to Visit Disney World:

Any time you visit DW can be a magical time, but if you’re planning a trip to Disney World, I highly suggest going in the off season. Not only is the weather more tolerable (we went in November and it was still in the 80s), but there are less crowds. Don’t get me wrong, the wait for some lines and attractions were still outrageous (we’re talking hours of waiting), and we were smashed like sardines at some points, but the amount of people visiting the parks was vastly different than if we went, say, in the middle of summer. And don’t even get me started on the heat. I can’t imagine being smooshed up against other people, being super hot at the same time, and still having the energy to walk around the parks. YUCK.

Also keep in mind when school is out for holidays and things like spring break, weekends, and when Disney World is having a big event (like marathons and the Epcot Food and Wine Festival) since that will bring more people out to the parks. We picked November only because that worked with my husband’s schedule, but it ended up being perfect for us. If you’re curious here’s a good starting point on when to visit Disney World.


The Cost of our Disney World Trip

One of the first questions people ask me (always under a whispered breath) is how much our trip cost. Here’s the thing: I’m pretty positive a family could easily blow their life savings on a trip to Disney World (and for once I’m actually not exaggerating about that), but I truly feel that Casey at Road Less Traveled Vacations had our best interest in mind and helped work with us to keep the price down.

The benefit of going when we did was that Julia was under 3 years old, so she and Madilyn were both free…for everything. We didn’t have to buy them tickets for the parks or a dining package. They ate off our plates, and if we needed something more for them (Julia) to eat, we just paid out of pocket for it. We also got our tickets (4-day park hopper) from ITT (the travel center) on base. Since I’m writing these posts to help you, here’s the breakdown of how much we spent, total:

How much it cost for a family of four (but more like two since the kids were both under three) to visit Disney World:

Room and Dining Plan: $1,898
Park Hopper Military Promo Tickets: $354 (for two)
Extras (souvenirs, alcohol, food/meals not on dining plan, etc.): $220

Total: $2472

That’s it. Not too shabby, in my opinion. We arrived on a Wednesday afternoon and left on Sunday, so we were there for 4 nights/5 days. We kept the cost down by picking a value resort (more to come in the next post), utilizing the military promotion rate for our park tickets, using our dining plan wisely, and not having to pay for the kiddos, but I’m pretty darn happy with that price.

If you have young kids and you don’t think it’ll be worth it to take them because “they’re so young,” think again. Not only will it be cheaper, but our two and a half year old had a BLAST. A “blast” is actually an understatement. We’ve been home from Disney for more than three months and I’m not kidding when I say that she asks if we can go back at least every other day. It was truly a magical place, especially for her young imagination!


Magic Bands

The reason why I know exactly how much we spent on our “extra” stuff was because that was all out of pocket…but we paid for it using our Magic Bands. Basically, the bands reminded me of how a cruise ship works. If you stay on Disney property, you get a Magic Band, which is essentially your lifeline while visiting Disney World. The Magic Band does everything from open your hotel room door and letting you connect your account to the many photographers around the parks to redeeming your Fast Passes and, the best part, you can “pay” with it. Everything was charged back to the room, so you sync your band with the cash register’s machine, and BAM, charged back to the room (which is really charged to whatever credit card you have on file). We bought a few souvenirs, paid out of pocket for a meal (or two), and used the bands to pay for things like alcohol, which isn’t covered on the dining plan.

Julia LOVED wearing her Magic Band, which we affectionately named “Toodles” during our trip. I didn’t bother with Maddie’s band since there’s no way she’d keep it on, and I liked that they were water proof since we hung out in the pool a few times and didn’t have to worry about taking our room key with us.

Planning a trip to Disney World and what you need to know before you go

In my next post I’ll share where we stayed on Disney Property (hint: it was “under the sea”), and give a review of our resort. I also have a couple other posts after that one, so if there’s something you’d definitely like to know about our trip, feel free to leave me questions in the comments and I’ll try to get you some answers!




  1. Yay! I’ve so been looking forward to these posts, we leave for DW in a month with our 16 month old. Can’t wait to hear the rest of your experiences at the park!

  2. Casey is taking care of my honeymoon arrangements and I am SO HAPPY to have her doing so! I know she will make this bride’s heart so happy and the fact that she is a military wife and understands my fiance’s (and soon to be, my) lifestyle is perfect!

  3. I LOVE LOVE LOVE Disney. We’ve been a few times with the kids and without. I can’t wait to get back to the mainland so we can go again. Although we’ll be on the West Coast so it looks like DisneyLand will be our best bet.

  4. Casey is the best!!! She helped us plan our trip for 2 to Disney and Universal last October. She even snagged us reservations for two of the restaurants where I really wanted to eat–and I started planning way later than you did!

    Most of us can’t really save money on lodging or tickets, which is the bulk of the cost for the trip. But we did save money on food and souvenirs by packing our own snacks/lunches and making our own Disney hats in advance. We did splurge on food in Epcot since we were there for the food/wine festival, plus our big character breakfast was in Norway.

    It was all totally worth it!

  5. Ah! Love it! We took Hadden just after he turned two and he LOVED it. And, like you said, it was great because he was free! We’re planning another trip for this fall when Hadden will be 4 and the new baby will be just 4 months (we’re probably crazy) so I’m interested to hear your other advice, especially about bringing a baby.

    1. Lol, I’ll give you the quick version of taking a baby: she slept—even at 9 months—almost the whole time! I can’t wait to go again…so much joy there 🙂

  6. I LOVE Disney and probably always will! One of the best jobs I ever had. I can’t wait to read the rest of your adventures!

  7. I LOVE Disney World! We just wrapped up our 3rd trip to Disney and we’re already deciding when we’re going to go again. We’ve always stayed at Shades of Green before but I think next time we’re going to stay on property so we can get the magic bands.

    Everyone always tells us not to waste it on our two kids who aren’t going to remember it but we love taking young children. My daughter isn’t even 3 yet and she’s gone 3 times. And every trip has been different because she’s been into different things. This time she had a blast meeting all the princesses and my husband loved watching her excitement. We’re crazy about Disney!

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