Hi Jason!
Welcome to planDisney! Thank you so much for asking this great Disneyland Resort
Magic Key question to us hEAR. I'm happy to be your planEAR today!
First of all, I don't think there's anything crazy with your three planned visits this yEAR. (I'm actually a bit jealous!) You'll definitely want to stay up to date on all of the park, resort, snack and holiday happenings by checking in with the
Disney Parks Blog as well as the official
planDisney Instagram account.
Yes, already-purchased
Disneyland Theme Park admission tickets can be upgraded to
Magic Key annual passes. The two ways to do this are through the
Disneyland Mobile App as well as in-person at the ticket booths in The Esplanade located between Disneyland Park and Disney California Adventure Park.
However, there are a few caveats. If you upgrade now you'll lose your current
Park Pass Reservations assigned to your day tickets as the pass reservations pull from different pools of availability for the different admission types. The best workaround for this is to wait to upgrade your February theme park tickets until the last day of your trip, after you've already entered the parks for that last day. Another tip is that you can
only upgrade to a Magic Key pass that is currently being sold, which at the time of this writing is the
Enchant Key. This is a pass with a few more limitations on when it's able to be used, so definitely double and triple-check the fine print that it will work with your triple vacation dates before you upgrade. And thirdly, while day and multi-day admission tickets are able to be upgraded to annual passes, typically only the value of one visit's ticket can be applied to the upgrade (per person), not multiple visits worth of admission tickets. I say typically because there's always a chance for some pixie dust, so if you've already purchased your Disneyland Resort Theme Park Tickets for the other two trips, bring them with you on your February visit when you make your in-person upgrade. Or, if you've planned the second two trips as
Ticket+Disney Resort Hotel packages, you have up until 30 days before check-in to cancel without penalty; you could cancel those packages, upgrade to the Keys, and then rebook the
hotels as room-only reservations.
I hope that this helped to clEAR your ticket question up, Jason. And if you have any more Disneyland Resort planning questions, We're All Ears!
~Kristen