We have sailed with the Pirates 3 times. The food is good. Chicken, Rib, pasta/potato salad. After being on the boat for awhile and snorkeling, the food is satisfying. Would I go on the cruise for the food - no - so I would say pick whichever cruise fits your schedule best. The cruise itself is alot of fun - so enjoy!!
The kids will LOVE Jolly Pirates! I don't know if it matters which tour you choose. We were on the lunch cruise which included dancing, food, beverage, the infamous rope swing and of course snorkeling.
You eat on the boat. I think someone caters the food, and brings it on board. It is all the correct temperature, and tasted very good. We are going to opt for the rope swing sailing though, since we have done the snorkel/lunch sail already. Not sure how many are on the boat at a time, but guessing 100 or so?