DON’T BE AFRAID TO ASK

James D. (NDD#152) (8 Posts)

A happily-married father of 4 children, James is a lifelong Disney nut. Ever since he found a map of the Magic Kingdom on his aunt’s refrigerator over 25 years ago, he has been obsessed with planning trips to Walt Disney World, whether those trips were for himself or for others. This obsession led to the founding of MousePlanning.com which provides concierge-level custom itineraries for people traveling to Walt Disney World.


Upon returning to Walt Disney World, just about everyone has their own favorite “moment” when the feeling of “being there” hits them.  For some, it’s when they first cross over that magical threshold from the real world onto Disney property.  For others, it’s walking on to Main Street, USA.  For me, it is the moment when I check in and receive my Key to the World card, so checking in to my hotel is always a magical moment. With over 30 trips to Disney World under my belt I’ve come up with quite a few tips and tricks when it comes to checking in.  Here’s one of my favorites:

Ask for the things you want.

You would think more people would do this, but they don’t.  Want a room on the third floor?  Ask!  Hoping for a room overlooking the water?  Ask!  Chances are that the Cast Member will try to find a way to make it happen for you. I will point out that there are a few factors that will play into whether or not you are granted your request.  You’re more likely to get what you want during slower times of the year, and the way you ask can play a role in the response you receive.  Sometimes, it just isn’t possible to get what you want.  However, there are always ways to stack the deck in your favor.

For example, in November of 2008, I took my mother, uncle, and brother for 4 day trip.  We were staying at the Polynesian.  We arrived on the Magical Express around 8:00 pm.  When I checked in, I chatted with the CM, letting her know that it was a special trip for my mom because she hadn’t been to Disney World since 1990.  When the CM handed me our room assignment, my mother (who had been coached by me earlier) excitedly asked me, “Will we be able to see the Castle from the room?” I then turned to the CM and asked, “Can we see the Castle from our room?” (Keep in mind that I already knew it was a Garden View room.)  The CM responded that it was not, but that she could check to see if one was available. As she checked, she said that there was a room available, but that the room cost an extra $125 per night. I turned to my mother and, as if she didn’t hear, told her we couldn’t do it because it was an extra $125 per night.  My mom put on that broken-hearted look and just said, “Oh.”  As if on cue, the CM said, “Hold on a minute, let me talk to my supervisor.”  Before you could sing a full verse of “It’s a Small World,” we were upgraded to a Magic Kingdom View room at the cost of a Garden View.

Some might call that cheating, or taking advantage of the system.  I disagree.  All we did was create the opportunity for a win-win scenario.  Here we were in the regular season, the only people checking in at 8:00 pm on a Thursday night.  The hotel was certainly not anywhere close to full occupancy, and there was no one behind us on line to check in who might get annoyed by having to wait a few extra minutes.  If it had been the last week of June and checking in at 1:00 pm with 75 people in line behind us, the situation would have played out far differently. As it turned out, Disney got some very happy guests at no loss to them, and we got a great view of Cinderella Castle at no cost to us, simply because we asked for what we wanted.

Polynesian Magic Kingdom View

All Because We Asked For It

Contributed by: James Dolan (NDD#152) James is the DDL Travel Tips Blogger. He is also the creator of Mouse Planning.

  • Shelley- NDM121

    Very interesting. I do ask at times but when given a no, I just leave it at that.

  • James

    I’m in complete agreement, Shelley. Asking gives a CM the opportunity to say yes if they can, but they know their limits. No one should ever be pushy or insistent if they ask for a perk and don’t receive it. That’s just being demanding and rude.

  • Ooh, I love the thought you put into this before you talked to the CM- that’s a great idea. Then you don’t come across as being demanding. Great ideas James!

  • James

    Thanks, Serena! A little preparation can go a long way.

  • Anonymous

    I love this story, James! We had a “girls only” trip back in 2009. It was my sister-in-law, my mom, and I. We were staying at Port Orleans French Quarter. We flew in from Seattle and used ME so we didn’t get to the resort until around 7:00pm. We were soaking wet because it was September and the weather was awful, but we couldn’t care less! The CM asked if we would excuse her for just a moment during our check-in and when she came back, she asked us if we’d like to be upgraded to a 1 bedroom at Saratoga Springs! I was the only one who knew just how cool that was! Of course, I emphatically said yes and they whisked us right over in a resort van and we were ‘home’ for 7days! It was completely amazing!

  • James

    Now that is a sweet upgrade, Jackie! It is those kinds of unexpected magical moments that really set Disney apart, isn’t it?

  • Katertotyay

    I liked your approach to the hotel room situation a lot. I’ve worked in retail and can tell you from personal experience you’re more likely to get what you want and a smile with it if you are pleasant about asking rather than being rude to the person working at the hotel (or in my case, a store). My family tries to do this as well and sometimes you get a great surprise! As long as you’re nice about it, I say go ahead and ask!