How I Approach Planning a Walt Disney World Family Trip

It feels strange to share this post that I started before our trip last winter, just before COVID changed life as we know it, but in anticipation of happier times to come, I thought I’d share a little bit about how I approach planning a family trip like this. I think Disney is the kind of trip you either aim to do once or twice with your family, or you fall absolutely in love with the parks and the experience and want to recreate the magic and return as frequently as possible. Since we fall very firmly in the latter category, I think our planning experience is worth sharing. And to say we’ve become near-obsessed with returning to Disney once the pandemic is over is an understatement.

How I Approach Planning a Walt Disney World Family Trip

Define a theme

One of the first things I do when planning a Walt Disney World family trip is to loosely define a theme or goal. It sounds dorky (because it is) but it helps me focus my planning efforts better to have this defined. On our most recent trip, since we were piggybacking off of what was a longer, much more relaxed trip with extended family, and Brian and I already got to do a lot of what we wanted when we visited the parks on our on last August, the goal is quite straightforward: to soak up as much Disney magic with the girls while spending as little as possible.

Let me backup and explain a bit more though. We’re based near Boston, MA so a Disney trip for our family will always involve a flight or a long car ride.  My thinking was that if we’re going to make the effort to pack up two kids for air travel to bring them to Florida for a family gathering, we’re a lot closer to Orlando and Disney World than we are up here in New England, so it just made sense to forgo an earlier winter vacation and only do it all once this winter and bring the girls back to Disney since our youngest is finally old enough to really enjoy it this time around.

When we went in 2018, we were in town for my best friend’s wedding, so the focus wasn’t on what I’d call the grand “family Disney trip.” I suppose I should note that this trip wasn’t that either. I think what I’m learning as we’re taking the girls is that we’re not going to be the family that only does the one big family Disney trip one time. While the girls are still young enough to be really into it all — the magic, the princesses, etc — we’d rather do more frequent trips with less pressure to see and do it all in one go. There are plenty of places we want to travel with them when they’re a little older, but while they’re game for the magic, we are going to make the most of it for as long as they’ll let us.

I absolutely LIVED for my older daughter’s face throughout so much of her first trip to the Magic Kingdom especially. Also, we’re slowly starting to introduce Emilia to Star Wars, and can’t wait until we can add Galaxy’s Edge to our experience.

We became Disney “addicts” fairly quickly. I say this jokingly, but there is some truth to it. At the time of the girls’ second visit they were only 4 and 2 1/2, respectively. Even during our “adults-only” getaway in 2019, when we stayed at Port Orleans French Quarter, Brian and I constantly talked about how excited we are to bring them to the Halloween and Christmas parties and how exciting it will be when they’re old enough to enjoy all of the “thrill” attractions with us, like Expedition Everest at Animal Kingdom and Space Mountain at Magic Kingdom. Of course, we discuss Disney Vacation Club often too.

Research Accommodations

One of the first things we sorted out was where we would stay. I learned about Disney Vacation Club rentals early last year, which sounded like a dream since I want to stay in all the Walt Disney World resorts, but we didn’t move fast enough in January, and missed our window to book. From my understanding, a DVC rental allows you just about all of the perks of DVC membership, only you’re not a true “member” because you’re just renting the points to book what is essentially a timeshare at the resort of your choice.

There are special websites that will coordinate with DVC members and book everything for you for a small fee, but I want to note that relying on a “rental” isn’t a sure thing — the rental coordination company merely does the legwork to find out if what you want is available for rental, often recommending you put in for a second or third choice option. I’d been looking into the Beach Club or the Polynesian (my favorite resort) before Disney released its “Free Dining” dates and almost overnight — snap — everything was booked! I learned the earlier you book point rentals, the better chance you have of scoring what you want.

We are lucky to have both good friends and family in the Orlando area, but we opted to kickoff the first leg of our stay with a really affordable timeshare rental preview we’re doing to keep costs down and put us in the WDW parks area. We have to commit to an early morning resort preview and sales pitch, yes, but considering what we are saving for accommodations, it is more than worth it. Since we’re planning to do parks, it’s not a huge loss to not stay on property, though that is my goal for our next Disney vacation. I was absolutely blown away by how lovely our recent experience at Port Orleans French Quarter was when we stayed in August.

Book Flights

Purchasing flights is the first thing I “officially” do, because the cost of airfare is often the determining factor as far as whether we travel somewhere as a family or not. We tend to try to fly mid-week too, on either a Tuesday or a Wednesday for better deals. For this particular trip, we coordinated around Florida’s in-state school break, which begins in early March. This meant staying at home for our own state’s winter break, which was rough! But for everything we said “No” to, like Disney on Ice, we consoled ourselves with reminders that we’d much rather splurge on other things when we’re in Disney World, so it helped with the sting.

Plan clothing

This is a big one for me. I like to look put together and cute, yet comfortable when I’m schlepping my weary butt from Adventureland to Fantasyland and everywhere in-between with my family. I don’t love matchy-matchy anything for my girls, and tend to steer clear of overly character-heavy outfitting too. I also avoid packing anything too “busy.” I always think about the vivid colors and visual chaos in the parks, which is why I tend to favor simple solids and neutrals. After reviewing photos from two past trips, I noticed I’ve worn the same pattern in two totally different shirts completely unintentionally. I guess I really love a black and white check to pair with my mouse ears!

I approach packing for a trip anywhere the same way a photo stylist probably does actually — thinking about the setting and the feeling I want to try to capture. I draw the line at expecting my kids to fake happy smiles though. My expectations for their “cheese face” is realistic and I recommend you keep yours that way too, for the sake of family sanity!

Disney is a tough trip to plan for because there is the long days/lots of walking factor for comfortable footwear is a must, but I find that sneakers really dictate what you end up wearing on top, so…. stress. See what I mean?

Reviewing pictures from our Epcot visit this last trip is a nice reminder that you can plan all you want, but at the end of the day, children have wills of their own and you have to pick your battles. Both girls insisted on their own outfit selection and at the end of the day, I’m fine with it. It’s not what I’d planned for them, but it’s totally OK!

Check the Weather, Park Hours and Loosely Plan Your Park Days

I use the word “plan” very lightly. I do a LOT of research and reading to remind myself of favorite attractions, shows, character meet and greets and food must-haves, and actually rely heavily on social media resources like Instagram and YouTube to discover new Disney treats and must-sees. Disney Food Blog is a perennial favorite over here. Brian regularly shares “what AJ has been up to lately” and what he’s excited about for our next trips and I don’t even pause anymore, wondering who the hell AJ is. [We love you over here, AJ!!] But more than anything, time of year and weather dictates our planning so we check that regularly as we plan and adjust accordingly. We tend to avoid Extra Magic Hour park days as well as visits during school vacation because park capacity tends to get CRAZY on those days and we maximize our Fast Passes the every extent of our power. We don’t usually park hop and haven’t had to leave the parks to nap the kids despite their ages, but as our family grows, staying within the “Resort Loop” is going to be more of a priority for our family to make this easier.

There isn’t anything that we’d be devastated to miss at any particular park, but it does help to keep a shared running list in Notes (we’re on iPhones) of favorite attractions we’d like to hit, the times of any shows we love, parades we want to see, foods we might want to grab and characters the girls might want to meet. The secret to staying sane though is not putting any pressure on ourselves to do and see it all in one go, which is why we’ve enjoyed our Disney trips with young kids as much as we have. Doing less but really soaking it in, watching their faces, and enjoying every single moment has been absolutely worth it in our opinion. Oh — and packing light for park days and using a single file double-stroller is key too for easily maneuvering through thick crowds. A doublewide is just not our style!

Stack of Disney Historical Books -The Disneyland Story and Triumph of The American Imagination

Read Up on Walt Disney and the Parks

I touched on this loosely above, but one of the best ways I ensure our trips are as magical as possible is to lean as much as possible into the history of Walt Disney as well as current information about the parks. I just love that Walt’s idea for the Magic Kingdom sprang from his Saturdays with his daughters. He’d take them to the park to ride the merry-go-round and slump on the bench, wondering why there wasn’t a place for families to have fun together. If what he created doesn’t sum up the power of imagination and pursuing a dream, I don’t know what does. I finished Robert Iger’s Ride of a Lifetime over the summer and start on The Disneyland Story next. Another one I have my eye on for Christmas is Ink & Paint: The Women of Walt Disney’s Animation. I also love to flip through park guidebooks, pour over maps, and review tips and tricks for park visits.

YouTube is a great resource for interesting facts about various attractions as well as a resource for up-to-date information about new foods to try, parades and shows, and other experiences worth checking out. Disney Food Blog regularly posts fantastic quality videos each week on YouTube and their Instagram account is absolutely droolworthy. I also love podcasts for trip prep. Two favorites are Unlocking the Magic and Resort Loop. Finally, for those who love apps, I found this collection of The Top 9 iPhone apps for Walt Disney World useful too. here

So that’s how I plan our trips. It involves a lot of time, thought and effort, but more than anything, one of the greatest parts about planning a Disney vacation is simply the anticipation itself. Leading up to a trip, we listen to favorite Disney movie soundtracks, watch our favorite films on repeat, watch walking tours of Epcot, the Boardwalk, and Magic Kingdom, read books about the history of Disney and talk about favorite memories from past trips. If this pandemic has taught us anything, it’s how excited we are to return to the happiest place we know. We can’t wait.


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