Don't be scared - we were all newbies once
Pirate Night is Tues, day 4, St. Maarten on our cruise and the Pirate IN the Caribbean party with the characters starts around 9:45pm....its not to miss! There is a pirate/caribbean themed dinner at your rotational restaurant with a mini-show by the staff as well.
So it depends how fast you eat...my DH and I like to take our time at Palo - plus we like to dress up in formal wear and get pictures done (they take one at the restuarant or you can get them done in the lobby every night of the cruise) so an 8:30pm ressie at Palo for dinner would NOT work for us.
We also like to dress up for pirate night in general so switching from formal to pirate would be a pain but if your routine is simpler than ours you might be able to pull it off.
I wouldn't want to miss either event, so I am sticking with my 8:30 ressie on the 1st night.
Hope this helps!