Hi Jessica,
Thank you for your kind words about the Disney Parks Moms Panel. We love helping guests to plan magical vacations! My daughter went to
The Pirates League and was transformed into an empress on a recent vacation. The experience there was amazing. The Pirates League space is immersive and fabulously themed, and the cast members were fantastic. It was fun for her as well as fun for her father and me to watch!
Between your options, I would suggest that you go to The Pirates League on the third day of your vacation. My reasoning is that you will all probably be excited already on your first day of vacation, and the first day is often very busy already, with arrival and settling into your resort. I would save this special activity for the third day of your vacation. I suggest making this reservation right after your Be Our Guest breakfast. Perhaps around 11:00 a.m. or 11:30 a.m. would work well. This way, there will be a long time left in the day to walk around as pirates! I should mention that if you choose the third day, you will likely miss the Adventureland Pirate Parade, which happens weather permitting and is typically in the late afternoon. At this time, little pirates can march in a parade. I have to tell you, when my daughter experienced her pirate transformation, there was no parade that day because it was during a crowded time of year, right around Christmas, so there was not really space to have the parade. At first I thought that this would be upsetting to her, but I quickly realized that for her, the experience of being transformed into an empress and walking around all day as one was the magic. To this day, she still wears her bandana from the makeover!
I hope that these thoughts are helpful for you, Jessica. Please do let us know if you have any further questions!