We did it when my two boys were 3 and 5. They LOVED it. So much so, that my 5 year old was expressionless in all of my photos, he was in shock and disbelief! I splurged for the full costumes, under the contingency that they would be used again for Halloween (and they were). I did bring pirate t-shirts from Etsy for them to change into when they got tired of the costumes, and I also brought makeup remover wipes because I had the dessert party booked and I wasn't sure how long the makeup would last. There was a downpour at 4pm, and the makeup ended up being a disaster after that, especially for the one who got the skeleton look (mostly black). I took them in the bathroom and tried to clean them up before we went to the dessert party but they both had raccoon eyes until they got back to the hotel and had a bath. So all in all, it was quite messy but it was a great memory. I did luckily find a photopass photographer as we were exiting the Pirates League. He didn't spend much time with them, even though there was no one else around waiting, but we did get a couple of shots in front of the sign that says "Pirates League". I'm very glad we did it, but its not something we would do every trip. This year, we are planning on doing the Pirates Adventure Cruise at the Caribbean to get our pirate fix.
