Call me the voice of objection, but I think doing the Pirate league in summer is a big mistake. In summer, the face paint doesn't wear well. It is often 100 plus degrees real feel, plus high humidity, and add a high probability of afternoon thunderstorms. Face paint + high heat + high humidity is not my idea of a fun. I've seen plenty of kids who look unhappy and often the face paint gets quickly smeared - again - especially in summer.
Personally, it's not really our thing - but I'd much prefer cooler months. I'm all for dressing up like a pirate!
It has been some time...but one fun thing we did enjoy was a haircut on Main Street plus hair glitter (not gel, just the Mickey glitter). the barbers were wonderful, and wearing the hair glitter is fun in any month. (theirs was more like Mickey confetti than actual glitter)
Still one more option we've enjoyed- doing our own pixie dust (a.k.a. glitter hairspray) just make sure to go OUTDOORS to spray it, so housekeeping doesn't have a big mess. We apply outside our room, then secure it (or not) with a quick spritz of hairspray. Most of it falls off before nightfall (so no glitter on the bedding). If you are going for the experience, then this may not appeal...We see the opposite, we keep our $$ and ride time.
Also, some of the glitter hairspray smells fine, some of it not so great. At $2 a can, it is wise to find out before you go which kind you have. It is easy to find at party supply stores, costume shops, some drug stores, at Halloween.