It took me quite a few tries to complete as expected, but in the end a mistake is what gave me victory. Upon start I did the usual attempt to manoeuver one ship behind the other while chaining the one in front...I didn't do this very effectively and was taking a pounding. I then ran to make repairs but I ran downwind instead of my intended upwind (off a few points), this was a mild panic at seeing my hull go bye bye. As I ran, I noticed that the enemy ships lined up behind me with the sail damaged one lagging behind, so like any good captain I began using my stern chasers to demast the lead ship...got them all by the time the lagging ship caught up to the slowing down front runner. Once the second ship came around, I just continued my tactic and demasted it as well.
Now free to manoeuver, I went back and selected more poor positions to sink them but was eventually successful after ~1h 15m. I had to do several repairs through the running to ensure I didn't sink.
Did this on the PvE server and then went on to the PvP server and did the exact same thing for the first try win in ~1h 10m. I only repaired once this time and only did that out of habit, it wasn't strictly needed.
Not pretty, not gallant, not heroic...but successful.