Sailing is the worst aspect of the game imo. Help me out.

[wmah]

Sailing is easiest to level up on. I often crew up one or two of the little guys and sink ships from a distance. I also play the two computer thing and use my second player as a gunner to hit the ship from a distance using lighting and then when the little guys can hit them with cannons I take out the masts and sails and let them hit them with their wimpy shots. This often gets me max sailing rep and they will often get max cannon rep. So it is a win win for everyone.

Also note that I avoid using the broadsides doing this and only use them when the enemy ship spawns right next to me.