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My first pirate, I played solo for the most part and sailing was the first thing he mastered, and primarily from questing. I crewed up as a crewman once or twice, and got to know another pirate that we did some plundering for, but I seldom did the sailing.
Plan your attacks, evaluate the surrounding area and traffic. All the enemy ships tend to sail in circles of sorts, predicting thier possible courses is not impossible. Remember that once you attack a ship, it will usually turn towards you and chase you, so try to pull them out of the pack from distance with a few solo cannon shots. If there is traffic nearby that may sail into your battlezone, you must be prepared for evasive action regarding that traffic (radar very helpful). Stay in front of, or behind the enemy ship your battling. Staying behind is harder, staying in front is usually pretty safe, although some of the ships can fire forward against you. Keep sailing your ship to the front of the other, using a full sail or ramming speed occasionally if you fall behind. This was called capping the T or something like that (an official naval tactic). The idea is to avoid your enemies broadsides, while keeping your broadsides to bear upon the enemy.
Groggy doesnt effect you at all while sailing. The only time it would play a role is in boarding a flagship and fighting the enemy hand to hand. It may also play a roll if you were involved in any direct cannon fire (on your pirate, not the ship) hits from an enemy vessel.
As your notoriety, and sailing level increases, your ships ability to defend, and inflict will also increase. I sorta think of those ship levels as being thier captains level combined with ship type (the way i'd figure your strength... level 18 sailing, war galleon, probably a level 18-20 ship to combat). This of course goes in hand with using the various skill points obtained to extend your broadsides strength, and the other various skills.
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