Hello Erin and welcome to the Disney Parks Moms Panel.
It does feel awesome to have all advance dining reservations booked.
I am happy to inform you that
The Pirates League opens from 9:00 am to 4:00 pm, and accepts reservations 180 days in advance.
The makeover normally lasts around 35 minutes, plus waiting time.
If you are able to make the 9:00 am reservation, there should be enough time to make the Cinderella´s Royal Table appointment, though maybe with a short run.
If by any reason you are a bit late, send the rest of your party ahead, as you will soon be joining them at Cinderella´s Royal Table restaurant.
Last December I had the opportunity to book reservations at The Pirates League, and my dazzling mermaid and fierce pirate loved the experience and make-up. This is one of their favorite experiences at Disney.
Interacting with Captain Jack crew is a great way to add lots of magic to the experience.
Remember to bring your own comb or brush.
Please let us know if we can help you further with the planning of your next Magical Disney Vacation.
Miguel