The Pirate’s League: To Arrr or Not To Arrr

After Pirates LeagueI waivered back and forth on booking The Pirate’s League situated in the Magic Kingdom’s Adventureland section. Disney describes the activity as “A rollicking good time where you get to be a pirate for a day with Captain Jack and his crew.” I read several online reviews which seemed positive and provided a peak into the experience: facepainting, costumes and pirate talk. It sounded like great fun for kids (and kids at heart).

But I had never before paid for any extras at WDW – no special tours, no cruises, no Bibbidi Bobbidi Boutique. There are just so many options already included in the price a Disney vacation; I couldn’t justify the extra cost. Plus we were traveling in August – would it just be too hot? Would the pirate make up turn into a sweat streaked mess as soon as we stepped outside?

But this was our first Disney trip as a family of four and the first ever trip for our son. Two years after adopting James Matthew, aka JM, and after months of cocooning, years of building attachment and mountains of paperwork we decided to go a bit bigger on this vacation. JM, then age three, adored Disney Junior’s Jake and the Neverland Pirates and our daughter Maggie, then seven years old, loved dressing up in princess costumes but was never into princess glamour makeup. She’s definitely part Aurora, part Goofy. So despite my doubts and tight wallet, I booked the Pirate’s League to add a little something extra to our adventure. And for $29.95 for each child, it wasn’t too much of a risk.

Welcome Aboard
When we checked in at The Pirate’s League, the kids chose their First Mate and Empress Mickey Minnie Pirate Shirtsmakeup features included in the packages. At check in parents have the option to purchase pirate hats and full pirate costumes. I decided in advance that the additional costumes would be over the top. Since we planned to tackle some additional rides after The Pirate’s League, I couldn’t imagine putting my already sweaty kids into pirate’s wigs, long sleeve shirts and pantaloons for touring on a hot August day. Also, by adding the costumes, the not-so-expensive extra would begin to fall out of that category.

So, a few weeks prior to our departure, I ordered Mickey and Minnie pirate iron-ons from With the sword, sheath, bandana, eye patch and more already included in The Pirate’s League base package, the iron-on shirts would be the final part of their ‘costume’. The kids didn’t seem to mind.

 Pirates League Ship's WheelPirate Names
After check in, our family was called through the large doors to an outer room where we met a member of the pirate crew. Each child spun a ship’s wheel to begin the process of discovering his or her pirate name.

After receiving each new pirate name, we waited on a bench deep inside The Pirate’s League for the kids’ pirate names to be called. Maggie and JM – I mean Jeanne Coalflint and Tobias Sharkbite – were called within just a few minutes of each other.


Extreme Pirate Makeover
 Pirate Tranformation Begins
The Pirate’s League room is dark, mysterious and somewhat beautiful – a great setting for a pirate makeover.

The pirate crew members were fantastic, relating to both kids as appropriate to their age levels.

As they applied the makeup, the crew members chatted with each child and explained what they were about to do. Maggie engaged with and talked freely with her crew member. JM was quiet, but would answer questions and break into the largest grins.

After completing the makeover, the crew member asked the kids to repeat the pirate oath. Again, each crew member adapted the long oath to the child as appropriate. When finished administering the oath, the crew member yelled loudly, “Yo ho! We have another pirate!” and everyone cheers. Maggie and JM beamed ear to ear.

Close Up with a Pirate Empress Pirate

To complete The Pirate’s League experience, the new pirates were given their swords and sheaths, coin necklaces and were taught how – and how not – to use a sword. They were then lead into a secret room for their official pirate photograph (available for an extra charge at check out). As parents we were able to snap photos and take videos throughout the entire experience except in the secret room. Upon check out Maggie and JM received a document with their pirate names and the oath. Despite my earlier penny pinching, I purchased the official pirate photo for each child. The Pirate’s League was just so much fun, I couldn’t resist.

It’s the Pirate’s Life for Us!
The kids participated in both the Pirate Parade and Captain Jack Sparrow’s Pirate Tutorial later that day. Maggie and JM wore their Pirate’s League garb for much of the trip, well after the makeup was removed. They referred to each other by pirate names and walked around saying “Yo ho!” and “Ahoy” for the rest of our stay. My husband and I referred to The Pirate’s League as the highlight of our trip and a memory that was well worth the price.

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Amy works as a college administrator and instructor in the Philadelphia area, where she lives with her husband and two children. She visited Walt Disney World for the first time as an adult for a conference. But Amy truly caught the “Disneybug” when she traveled with her young daughter. Amy loves all things travel and especially enjoys trip preparation and strategy: trying to find the best deals, exploring new resorts and restaurants, and planning an extra something special for each trip.

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