On our 2014 trip, one of the surprises for the boys was a tip to The Pirates League for a Pirate Makeover!

The Pirates League is located in Adventure Land in the Magic Kingdom, right next door to the Pirates of the Carribbean Attraction and accepts reservations 180 days out just like Table Service Dining.

There are a multitude of looks that your little buccaneer can choose from. In our case we had two Jakes (à la Neverland Pirates) and a Captain Hook.  Mermaid and Empress options are also available, but our little princess was too young at the time to partake in the makeover.  You must be over 3 years of age and when I asked why, I was told that the make-up products used were rated/tested for ages 3 and up (A little bit more below on how we included our daughter in the process even though she couldn’t participate in the makeover).

We arrived about 15 minutes prior to our appointment and the boys were asked to choose the Pirate Look they were going for from a menu with pictures of each of the looks.  Then it was time to take a pirate oath and receive a  new swashbuckler name!

The ‘transformation’ room is wonderfully themed.  The walls are faux timber, stone and stucco; flags hang from the ceiling, and all the make-up artists are done up in their finest pirate garb!  There’s lots of pirate chanting that goes on, and the cast members that we had seemed to really enjoy initiating our little land lubbers to the ways of a pirate!

Our son was very shy, but others that were having their pirate transformations done really got into the spirit!  The make-up artist we had was very gentle with him, and told him what she would be doing each step of the way.  For example, when it was time to make his 5 o’clock shadow; she let him have his own sponge to hold while she worked.  After a few magical moments, the transformation was complete, and we had a little pirate!

The boys were asked to take another oath while they were presented with their pirate league sashes and swords, and then it was off to a secret chamber where they followed a few clues and found gold medallions!  After a few photos with the photopass photographer, the boys left the secret chamber, and were presented with their own pirate certificates with their new pirate names!

Sharing this experience amongst best buddies was even more fun.  The boys really enjoyed seeing each others transformations, and would come up with Pirate scenarios together throughout the day while waiting in line or walking around.  And the pictures together were of course adorable!

We then dedicated the rest of the day to exploring Adventureland and Frontierland.

Quick tips:

  • the costume make-up they use really sticks once it’s dry – we had very little smudging, but it means it’s hard to remove with just soap and water.  Our son walked around the parks with ‘gentleman’ eyes for the next 2 days despite a serious amount of scrubbing.  Next time, I’ll be sure to pack make-up remover wipes for this reason.
  • You’ll be invited to come back later in the day to do some pirate training and to participate in the Pirate Parade.  The boys loved participating in this, and there’s a photopass photographer present to capture all the swashbuckling memories!
  • If you have any children that are too small to participate in the makeover, pack a costume for them to dress up in while you are waiting for your older kid to finish up their makeover.  In our case, we had packed a Tinker Bell costume for our daughter who was 2 at the time to change into.  (pre-Zarina)