Welcome aboard, JanaLee! Your family is going to have such a wonderful trip on the Disney Fantasy at the end of this summer! I can't think of a better way to wrap up summer fun, than with a Disney Cruise Line vacation!
Pirate Night on the Fantasy this August will most likely be Night 4, St. Maarten night if you're on the Eastern Caribbean itinerary, or Night 5, Cozumel night, if you're on the Western Caribbean itinerary.
I'd suggest trying to book the pirate makeovers around 3:30 or 4:00 that afternoon. This will ensure you're back from your Port Adventure, and still leave enough time to make it to Main Dining, or the first show in the Walt Disney theatre that night, depending on your meal seating time.
Keep in mind, though, that if this is your first cruise with Disney Cruise Line, your window to make reservations for the the
Pirate's League in the Bibbidi Bobbidi Boutique won't open until 75 days prior to your sailing. Castaway Club Members (those who have sailed with Disney previously) will have been able to make makeover reservations prior to this, so there might not be many time slots left. Be sure to log into your reservation on the Disney Cruise Line website that first day that you are able, so that you can choose your time before they fill up.
My son has some amazing memories of being transformed into Black Beard in the Pirate's League onboard the Fantasy last year. It is well worth the cost to allow you children to experience such a special treat! Please let me know if you have further questions as you continue to plan your cruise, JanaLee! I'm happy to help!