There are some good recommendations here, I usually use most of them, except the big crew. For my advantage in sailing, I always try to be the fastest, most maneuverable ship there, even when sailing my Gallon O'War. To do this, I Max Windcatcher, and keep at least 3 points in tracking and Full sail. But It's not all about dodging attacks, for me, it immense firepower. For that, I Maxed Round Shot, Barrage, and both my broadsides, trust me, this will make the damage of your broadsides to the 7th power, you become almost invincible with it, doing 1,100+ damage per broadside shot. It's so powerful that you can sink a Ogre with open fire in 1 broadside of a Sloop O'war. I would also recommend taking some to get used to dodging attacks from ships, just stop when they fire of use Come About.
Hope this helps,
Nuju-
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