Hello Erin!
Welcome to the Disney Parks Moms Panel! It is a pleasure to answer your first question.
My 6-year-old daughter absolutely loved her pirate transformation at
The Pirates League. It is SO much fun, I just simply cannot stress that enough. The place is just amazing! You feel like Captain Jack Sparrow might come out of the blue at any moment.
We had a 10:30 a.m. appointment, and were finished about an hour later. I saw other families come in after us and finish their transformations in as fast as 40 minutes, so it also depends on the package you choose. Our bucaneer selected the Empress Package.
I personally think that you will have issues with timing. You need to be at
Harmony Barber Shop some minutes before your appointment, which means you might rush things over at The Pirates League. I don’t think this is an ideal situation because I am sure you have carefully planned this experience for your children. My daughter arrived and chose her pirate name, she went through the transformation, said her pirate oath, and then went into a special pirate room to look for a treasure inside a chest! The interactions with the Cast Members were just amazing and we made memories that will be cherished forever.
If possible, I would book a later appointment at Harmony Barber Shop or adjust the reservations at The Pirates League. In addition, you need to travel between destinations, and even though they are about a 15 minutes walk apart, touring with kids sometimes requires detours, like a restroom break, for example.
I hope this helps you while planning and that you are able to enjoy both experiences.
Best magical wishes,
Thiana