Ships of the Line=1 Shot
I did this on a thief (medium armor) with 16,705hp and while one rock nearly one-shotted me, it was not quite. Most times I could raise the shield in plenty of time to block both incoming shots, and watch the target circle to dodge the rest of the time.
I beat this first attempt, and only died when I was on the shore. You either are not timing the shields right or not dodging wen target circles pop up.