Hi Kaitlyn,
Nothing is better than a little bit of pixie dust in the form of a free room upgrade! We visit Disney World a few times a year and have only received the magical news of an upgrade once. It was during a slower season for visitors, and it was just a better view. While it is super fun to get that magical upgrade, I would not expect it during the high-traffic holiday season, when Disney World operates at full capacity. While it doesn't hurt to ask, the possibility is pretty slim because most of the rooms will be fully booked.
If you want to spread a little bit of pixie dust on your own vacation, check out the
Enchanting Extras Collection. We love picking one of two of these fabulous experiences on each of our vacations to try something new and add a little bit of extra magic to our trip. My favorite experience is the
Wild Africa Trek. We have done this tour multiple times and love getting up close with the animals and hearing all about their care and keeping from the people who know and love them best. This tour also culminates with a fabulous snack out on the Boma where you get to relax and enjoy the view.
Since the
holidays at Disney World are so special, several of the events will sell out if you wait to book them. I recommend going ahead and purchasing tickets to
Mickey's Very Merry Christmas Party as soon as you can confirm your dates to ensure that tickets don't sell out before you get a chance to secure your spot! Don't forget to check out
EPCOT's Festival of the Holidays while you are visiting. This event is included with your ticket price and features festive food booths, storytellers, and holiday magic from all over the world.
Happy Planning,
Jenna