where to level cannoneering

[Poison elf]

This as other skills can also be worked together. Park your boat near a enemy ship just on radar. Use your cannon to hit the sails, soon as you hit the ship first time it will head at you. When its lined up like that you can shoot the sail mast, knocking sails down.

After you have shot off all the sails you can go to the wheel and start using broadsides until sinks. Getting rep in both sailing and cannon.

Takes some practice to shoot sails down, and you may have to jump to the wheel and pull back at first.