Hi Lea, and welcome to the Disney Parks Moms Panel. I am the Queen of adding days to my Walt Disney World Resort vacation, and I also love to add days at a different resort hotel. This way, my family gets to relax in double the pools, try double the resort food and snacks, and explore double the theming. What's not to love about that?!
I reached out to a Cast Member, who confirmed that you will not be able to apply two sets of tickets to an
Annual Pass upgrade. Thinking through your travel details, it will be up to you to determine which will have a greater value: the value of the tickets attached to both reservations, or the value of an Annual Pass? Will you be visiting again within a year? Don't forget to factor in the included theme park parking, Memory Maker, and select dining and merchandise discounts. I became an Annual Passholder last year, and I believe it has paid for itself when I factor in all the
great perks – but beware: you will ALWAYS want to be at Disney World once you have the "keys to the kingdom."
Lea, if you want to upgrade your first set of tickets, you'd then need to modify your second reservation because you will no longer need the tickets. If you upgrade the set of tickets attached to the second package, you won't get the value of the tickets from the first reservation. I feel a bit like The Mad Hatter with this answer, and I don't want you to be confused, so my advice is to contact the friendly Reservations Cast Members at (407) 939-1936. Make sure you have both reservation numbers handy so they can best assist you and help you to figure out what makes the most sense for your visit.
Have the BEST time on your extra-magical visit this August, and please come back and see us if you have any more questions as you count down!
Wishing you a magical vacation,
Robyn