Ah, so the way I have been raising my sailing experience is the only way you can! I thought I was doing it wrong, since it takes FOREVER!
I spent about 2 hours yesterday, raising my level from 3 to 4. (The sad thing is that we will all have to start the game all over! I am notriety 11, and cannon 11. Shooting cannons is my favorite! Not so hot with the rest!) I sail alone most of the time, so play the spin the ship game! So, if you see a ship named Shadow Runner spinning around, it is me, Molly O'Hara!