I have total empathy since I have a houseful of boys who have never been interested in princesses. The closest opportunity for dining with pirates is at
Hollywood & Vine at Disney's Hollywood Studios, where Jake the Neverland pirate visits along with Disney's Little Einsteins, Handy Manny, and Special Agent Oso. There are also some non-princess dining experiences your son may enjoy (just click
here to read more about all of them):
Cape May Cafe, Chef Mickey's, Mickey's Backyard BBQ have Mickey & his friends
The Crystal Palace has Winnie the Pooh & friends
The Garden Grill has Chip 'n Dale
'Ohana has Lilo & Stitch
Tusker House has Donald Duck and his friends
50's Prime Time Cafe makes guests feel like they've gone back in time; it's a hoot!
Whispering Canyon Cafe has lots of cowboy antics and fun
Sci-Fi Dine-In Theater provides guests with feeling of being in an old drive-in theater from the '50s & '60s
I also have to tell you about a few other pirate experiences with
The Pirates League, the
Pirates & Pales Fireworks Voyage, &
The Legend of Jack Sparrow. There aren't character dining, but still lots of fun for fans of pirates.