Can you upgrade your Disney tickets to an annual pass?

Can you upgrade your Disney tickets to an annual pass?

by Ashley
(New Jersey)

I'm planning a vacation for late August and want to get the free dining plan, but considering I'm going to Disney in the next April than next July, I wanted to get an annual pass to save money. Unfortunately though I can't get the free dining plan if I don't buy my tickets through the package, so I was wondering if I booked the vacation, if I could go to the park to upgrade my tickets to an annual pass.

Have your Mickey Bar ...

The cart for Mickey Bars

Photo by Miss Millificent

Dad’s how to have your Mickey Ice Bar and eat it too Answer


Disney is pretty good about offering families ways to save and make their trips to Walt Disney World more affordable. Whether it’s free dining, discounted hotel rooms, the-longer-you-play-the-less-you-pay-per-day, or any of a number of other offers, if you’re a savvy shopper it’s very likely that you’ll find a way to save on every trip you take. But don’t forget – Disney needs to make money too and they’re pretty clever about making sure you only take advantage of one discount at a time.

Now, that doesn’t necessarily mean that we can’t find a way to be MORE clever about maximizing our savings! Dad’s been on the case researching your situation, and while there’s no easy cut-and-dry solution, there are a few things you can try to combine the savings on an annual pass with the added value of a free dining plan.

The first thing you’ll want to try is good old-fashioned arithmetic. If you’d rather pick one discount over the other, you’ll need to do the math to figure out whether free dining or the annual pass will save you more in the long run. As a general rule of thumb, the Annual Pass is worth buying if you’re planning to spend ten or more days at the parks in a year. But will it save you more than free dining on one of your three planned trips? Maybe, maybe not.

Dad’s Walt Disney World Annual Pass Page

Here’s what you should do: determine how many days worth of park tickets you’d need to buy on each of your trips, and then price out Magic Your Way tickets for each trip (for example, a 5-day trip, a 3-day trip, a 7 day trip). Take that price and subtract the annual pass price. Whatever that number turns out to be, we’ll call is Discount A.

Now let’s talk about the Disney Dining Plan. Dad never thinks it’s a good deal, unless it’s free. In your case, the question is whether it makes sense to get free dining for one trip and pay for food on your next 2 trips (since there’s no way to tell at this point if Free Dining is ACTUALLY Dead).

So, head on over to Dad’s Disney Dining Plan Calculator, and tally up what you’d spend on food during your August trip and we’ll call that Discount B. After all of this, all you have to do is look at the numbers. If Discount B is larger than Discount A, go with Free Dining! If Discount A is larger, get yourself an Annual Pass! Easy, right?

If math isn’t your strong suit, or if you really want to make the two discounts work together, there are a few more options. You can book your Magic Your Way with Free Dining package for August, and at your hotel, explain that you’re interested in upgrading your tickets to an annual pass – they might be able to do it right on the spot even if this option isn’t available to you by phone or online in advance.

If that fails, you can always book your return trip in April while you’re on your August trip. Disney calls this a Bounce Back offer, and it works by offering you a very nice discount on a future stay (typically a stay within the next year) as long as you commit to the trip by booking it before you go home. It’s a great bargain for families who are ready to sign up for another vacation before the current one ends!

Finally, you can be sneaky and try to out-smart the folks at Disney – have your Mickey Ice Cream Sandwich and eat it too. Here’s what you’ll do: book your August trip for as many days as you like, including hotel and free dining for your length of stay, but only add on one day of park tickets (that’s all you need to “activate” free dining). On your second day at the park, simply buy an annual pass to use for the rest of the year. Then reward yourself for being so clever with an actual Mickey Ice Cream Sandwich. (Don't know how much actual money this will save.)

You could always just turn all of this over to the professionals and let them figure it all out. That's right, the Disney Vacation Planners (Pixies and Pirates) over at Pixie and Pirate Destinations know all the tricks and will be able to help you pick out the best option. Go over and talk to one of them. You won't be sorry. Trust me.

Pixie and Pirate Destinations

Dad's Bottom Line

Ashley, thanks for the great question. Dad loves getting the chance to think outside the box about the best way to save on Walt Disney World vacations. Let me know how your hunt for savings unfolds!

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