Yes you can!
Did you know the date your annual pass starts is the first day you use your park hopper, so if your first park day was December 1st and you upgraded to an annual pass on December 7th, your pass would be backdated to December 1st. The cost of your pass is the difference between what your park hopper is worth and the cost of an Annual Pass.
Note that you can completely use up your park hopper and still upgrade it if it’s within the 14-day period. You can even update it from home, although it’s a lot easier to do it at Disney World.
One thing. If you bought your park hoppers tickets from a discount broker like Undercover Tourist, you probably paid $10 or $20 less than what Disney charges. Use your park hopper at least one day and you’ll get the full Disney price that day (even if you bought your tickets prior to a price increase). If you don’t use it, they’ll only give you the price that you paid your discount broker. It’s a funny little quirk with the system, but it will save you money, which is nice when you’re buying multiple passes.
Hope this helps!
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