I was really hoping my son would enjoy this, he is 4.5 years old. I made a reservation about 1.5 months in advance (not sure that's necessary, but I did it.) Anyway, my son loved it! It was such a fun experience and I am honestly surprised Disney does not charge more because I walked away feeling like I got every pennies worth. We did the basic package which included face paint, a sash, a sword, a pirate tattoo, a certified script proclaiming you are a pirate, a 'treasure necklace', and then some really cute pictures in a private room for your photo pass. I highly recommend! It did take about an hour and I recommend taking one of the later appointments because the face paint would and did smear throughout the day.
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