I got chased from the entire length of the map a few times. This brigantine chasing my solo sloop never gave up.
I made a last minute mistake and misjudged my turn and crashed.
I broadsided them and they boarded and killed me and sunk my ship.
My best tip I think, is to drop them a message.
Sent them a message "GG".
They replied "Same to you"
Said GG to the other and he replied "You made us work for it! Lol"
Turned out they were Duo brigging. So they invited me as a third crewmate due to my friendly disposition.
So not only did i cash in my lost loot, i cashed in theirs and another poor pirate sloop that we happened to run down.
We killed them a little quicker with me on the cannons though!
So best tip, drop them a GG.
It might lead somewhere. At the very least they'll know you arent a salty pirate but a good sport. Even if deep down you are seething! Haha