The only whay I have gained sailing skill was when I stayed at the helm during battle, which means someone else needs to be with you manning the cannons. I have very little sailing because I am not very reliable on my connection (added to the normal freezes and crashes it can get crazy) and I just sail alone or cannon for people.
I went to the link and broadside cannons for the light galleon and frigate are also sailing exp. You dont have broadside cannons on the sloop.
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