When boarding an enemy ship, to determine the winner of the skirmish you will fight the other ship's captain. So, if you have 40 men, and your opponent has 350, he's taking you down in one swing. Here, this is my last joke, I made it up all by myself. Now that I've praised the game for its playability, I have to scold it for throwing that all away early on. This game is simply way too hard to get into as a beginner.
Random encounters happen way, way too frequently.
You will never have a journey with no random encounters, and if you're going any sort of distance, expect to fight. When you are attacked, enemy ships begin right next to you, meaning you can expect to get fired on right away. This limits rookies to three close knit islands, which frankly, is flat out lame. Sailing the vast ocean shouldn't resemble rush hour traffic. Trust me, I don't care how opposed to constantly saving you are, quick save and quick load will become your two best friends.