Of course you can, but with the thousands of different outcomes the game can produce it all comes down to you. But maybe I can try and help a little. That's where this video comes in. I will give you some tips on the "what" and "how"... we cover a lot of things.
This is an oldie but a fun one for the newer players to show how to escape even the most skilled pirates. Yes I know I just run away here, haters :), but there was a plan in everything I did. This was early on when not a lot of people knew Sloops could outrun Galleons.
For my first video I just felt like doing a quick little delivery. Went pretty smoothly until the storm midway. Wow, it did a number on my ship. But I made it through and continued west to successfully deliver the crates to their destination.
Was actually minding my own business for once (after the first galleon sink, it was a solo player so we don't count him) and I spotted a Brigantine headed for me so I snuck off with the loot in the rowboat and let them sink my ship. I sold and tracked them back down and attempted to ambush them but they scoured the island due to the mermaid being present and eventually found me. Annoyed but determined I went to the final island in the mission and ambushed them there, this time successful.