Travelling from Istanbul to Tripoli, Pirate Boss Barbaraso II appeared out of nowhere and  attacked my ship. Barbarosa II spawns just south-west of Crete Islan.

I have no plans nor was I hunting Barbarosa.  I was on my way to Tripoli to complete a Quest when out of nowhere a Golden Eye Raiding Ship appeared and attacked me. I did not know it was Barbarosa II, I thought it was just your everyday Golden Eye. Clicking the Attack button, I was suprised to see that it was Barbarosa II that I was against with when I entered the scene and targeted the raiding ship.

It was an intense moment. I've never faced a Pirate Boss before and I've heard from Bravostar, a guildmate, that Barbarosa II is tough.

I was not prepared, my ship's crew was down to 42 and I was already thinking of defeat.

Like any raiding npc pirates, Barbarosa II rammed my ship and dealt 1,500 damage to my hull. He then tried to grapple (I saw something shootout from his ship's deck) but failed. A cannon fight began. Side by side we were trading cannon fires but I had to give in. My ship can't and will not win by cannon fight. So, I moved in closer and once close enough I grappled. I was successful and boarded Barbarosa II's ship.

With only 42 sailors, me and my crew were outnumbered. 

I tried many times to target Barbarosa II but he was inside this throng of fighting sailors. So, I waited near him. He killed one of my crew in an instant and then turned his sights on me. At this point, all of my crew were already killed and I was mobbed by Barbarosa II's crew.

The amount of damage I was taking was enourmous. I was very fortunate to have a huge supply of low level HP potion with me. Taking in as much potion as I can as I absorb all the damage being dealth by Barbarosa II and his crew.

The fight rages on. I was so excited to see that Barbarosa II's HP was lower than mine and was getting lower faster than mine. With about 25% of my HP left, Barbarosa II fell in defeat and with it the battle ends. He dropped a few drawings, 2 level 4 figureheads, some quality cannon balls and some silver.