Sailing is the worst aspect of the game imo. Help me out.

[Will Badbreaker]

I have had great luck sailing alone. I often get 100 rep with many ships. I attack them from a distance to get them to notice me and work my way to their rear. From the rear I broadside them, and hit down arrow (pull up sails), once I'm behind them fully, I turn to the other side and put the sails up and broadside again once next to them.
This works great as I hardly take any damage, they even stop shooting after a short while. It takes a few broadsides but it works for most ships.
Some ships will keep drifting and I have to drift with them instead, but overall this tactic works for me.