Confessions: 6 mistakes I’ve made planning WDW trips – PREP011

Over the years, I've made some mistakes when planning Disney World trips.

Today, I'm sharing 6 of those with you, including 1 that I made earlier this year.

I'm hoping you'll learn from things I've done wrong and avoid doing the same on your trip.

I've also got a tip for you on where to order Disney gifts that can be shipped to your house.

These are notes from this episode. There's much more info included in the audio so be sure to listen to the episode for a better explanation.

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6 mistakes I've made

Over the years, I've made several mistakes when planning Disney World trips. Here are 6 of them.

Mistake #1: Not allowing enough time for transportation
Allow for at least 1 hour to get anywhere. Having your own car or taking a taxi can reduce that but you should still allow 30-45 minutes each way.

Check out my guide on how to navigate with Disney transportation for more info.

Mistake #2: Choosing dining that's not close to where you are
In the 6 step planning process, I advise you to make a daily plan and then choose your dining. The reason I suggest that is so you are making dining choices based on where you'll be and not running around to your dining reservation.

Mistake #3: Planning too much
Be realistic about what's possible, pare down your plans and allow for some unplanned time.

Mistake #4: Not including all family members in pics
Use PhotoPass photographers to take your pics and/or hand your camera to the photographers to take your pics.

Get more info on how PhotoPass works.

Mistake #5: Booking flights based solely on cost
Consider flight schedules and reduce the number of connections if at all possible. Use to research the reliability of flights before you book.

Read my tips on finding the best flights for your trip.

Mistake #6: Not using resort check-in
You don't have to be taking Magical Express to use resort check-in when flying home from your Disney World trip. Anybody flying home on a participating airline can use resort check-in which will allow you to bypass bag check at the airport.

For more detailed info on Magical Express and Resort Airline Check-in (including which airlines participate), read my guide that covers all of the info.

Quick tip of the day

Disney Florist isn't just available when staying on-site at Disney World; you can also use Disney Florist to ship things to you at home. Get ideas from their Celebrate at Home section.

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Romo Ruz

I have been three times since the Fast Pass started. The first year was a complete failure. Always looking at the time and the land we were on and walking from one side of the park to the other instead of enjoying the attractions. Once we even walked out a Character Dancing Thingy in front of Country Bears Jamboree so we can go to a FastPass in Under the sea. The second and third time were completely different. We stayed for 14 beautiful and great days onsite with ten days of tickets plus Extra Magic Hours, so we enjoyed the… Read more »


just want to add a mistake we made early this year… letting your FASTPASSES control (& almost ruin) our day we found ourselves going from fastpass to fastpass & not enjoying ourselves. Finally we decided to just have fun, fit in our FASTPASSES as we could & ignore them if that worked better. Hope this makes sense. It worked for our large multigenerational family those 3 FASTPASSES added a whole new level of stress for this official grandma planner #stilllovedisney

Craig Williams

Hi Shannon, Hello to all the people who read and give me your feedback on this post also. I love these podcasts so far and I intend working my way from the very first up to the newest one before I take my family with two children aged 10 and 7 in September for the first time. I feel that now is the age where they would appreciate the main Disney Land as we live in Wales in the UK and have done Disney Land Paris 3 times in the last 10 years and feel that it would be magical… Read more »


Great podcast as usual. I recently made a big mistake with Resort Airline Check-In Service that I would like to share. We typically fly Southwest, which does not have assigned seats. Passengers are able to check in online up to 24 hours ahead of the flight, and get put into their boarding groups based on the order they log in. They explain it better than I can: “At Southwest, we have a quick, easy, and efficient boarding process. Check in to get assigned a boarding group (A, B, or C) and number (1-60). This is your spot in line. Remember,… Read more »


I cannot believe I just learned about the resort baggage check in for departure from the most recent podcast! I honestly thought this was only and ME perk. We are car people and don’t take ME, so I am beyond amped about this! Thanks Shannon for this great reminder.


Thanks for reading my iTunes review in this episode!! 🙂 Great tips as usual!

Becky Creviston

We just returned from our trip to WDW (Sept. 20 – 28). We used the FP+ system and loved it. You only get 3 per day/in one park, so it leaves plenty of room for flexibility. I’m a planner and dislike the idea of “running” to a kiosk to get a fastpass…so this system works well with me. Also, depending on the crowds, you might not need to use the FP+ system. There were some rides that we used our FP+ (because we had it) and the “Stand By” line was 5 minutes. I would have used the FP+ system… Read more »


Question about the photopass. We’re going during week of Christmas 21-27. During this time do you think it will be too busy for photopass photographers to be out taking pictures?


My advice is, if you are there for rope drop, use those early morning hours wisely. I knew this on our first trip to Disneyworld, but for some reason I thought it would be a great idea of get a ” pawtograph ” from Lady and the Tramp as we exited Town Square Theater. I should have stuck to our itinerary and went straight on to see Tinkerbell before her crowds grew. Instead, we wasted about 25 minutes trying to get the pawtographs. Now, I understand that it wasn’t a big deal in the whole scheme of things and we… Read more »


Great tips! As we are wrapping up the details of our trip in November I am trying hard not to make mistake #3. But I feel Disney is making that harder. With ADR and now FastPass+ it feels like you MUST have every minute of every park day planned out if you want to see/do everything on your list. We’ve decided to forgo FP+ so we can have more flexibility.




We have used FP at times, but if you get to a park when it is open early and target the rides that you want to do most, you can get on a couple pretty early. You have to be an early riser 🙂

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