Yeah, they make you pay to check a surfboard, but you can tell them the skimboard is a boogie board and they don't charge you.
Pack towels and all kinds of soft stuff around them or they will get damaged by the clowns who throw the luggage on the planes.

Yes good shorts, are critical. I found out the hard way skimmin' in St. Maarten one day. I had to walk around town holding my pants away from my pecker so that the tip didn't brush them or it was pain.