Went with my family on the Jolly Roger in November. We had a fantastic time!!! As for the tipping on this excursion a tips box is left at the ship exit. The crew has no idea how much is placed in the box by each individual. We received EXCELLENT service and tipped accordingly. I believe my husband tipped 10 dollars and I threw in an additional 5 dollars when they offered to make a return trip to retrieve a digital camera.
Warning -- This is especially good for the 12 and under crowd in the beginning. Kids are lined up, yelled at, take a pirate oath, and scrub the deck. They will get wet!!! I tell you this b/c one teenage girl was very upset that she was included with the "kids" and didn't like it when she was soaked wth water. Tell your teen to decline partcipation if this isn't his thing. Another warning -- stand back when they ask your kids to bring their parents to trial unless you have a great sense of humor. We had a fantastic time but some other adults were happy to watch but would not participate.
This was the talk of our vacation - the crew was incredible and went out of their way to go way beyond the call of duty. Your teen will love to walk the plank and can even jump from the upper decks (which I did during a temporary loss of sanity). Hope you have a great time. I have some wonderful pics. Let me know if your interested.