Wow, that's a tough one as they are both so much fun for kiddos and so enjoyable to watch as parents. I'd say, if your son is adventurous, then the pirate excursion would be perfect for him. My twins did both last year (they had just turned 6), and loved both. The Pirate League is adorable and as others have said, he'll get comments the rest of the day. You'll be able to watch him throughout, and the "real" pirates were great with my constant picture taking. However with that said, I'm tempted to vote for the Pirate Adventure because my two just had sooo much fun. They loved going to the different locations to search for treasure, and the fact that they were going without us, made them feel so independent. We didn't tell them what they were doing until we got to the marina (POR), and when we told them, they were happy. But when they learned it was for kiddos only, they were thrilled. Don't know if I should've found it cute or insulting?! You could always do your own pirate make-over on him for the adventure? If you do that remember anything he wears will be covered with a safety vest. Also, if you do opt for the adventure, make sure you are there to watch when the boat returns. If the excursions are mostly the same at each location, you'll be able to follow him and watch his last search for treasure....super cute! You can't go wrong...he's gonna love whichever you choose! Have a great trip!