Hints:

Hint 1:

Never drop your sails in battle--there's just no need. Maneuverability is always important when you need to get your other cannon facing toward the enemy as quickly as possible.

Hint 2:

When you begin an adventure, loot towns first to get enough money to buy another small ship (approximately 1,500 gold pieces, depending on the port) before you go off to try your hand at open-water battles.

Hint 3:

Before you start in on a long series of sea battles, recruit as many sailors as you can fit onboard; you'll need them for the boarding operation against even a minor opponent.

Hint 4:

Before you disburse your plunder to end an adventure, head out for one last strike on the open seas to kill off a few of your crewmen (and bring in some extra cash). That will make your split much more attractive once you reach port.

Hint 5:

When going after a ship, begin by switching to Chain Shot, and attack only the sails for a few passes (that will slow the enemy ship down). Pull back and switch to Grape Shot, and hammer away at the deck (that will kill off enemy crewmen). Once you've made a good number of strikes, issue the grapple order and begin boarding--hopefully, the odds will now be in your favor.

Hint 6:

You may find things easier if you stick to a single ship and upgrade, rather than increasing your fleet (besides, you'll have less worries about doling out the plunder later with fewer pirates under your care).

Hint 7:

Whenever you get a ship to surrender, secure it and take it to port to sell. Don't press the crew into service; they'll mutiny on you at the most inconvenient time.

Hint 8:

If you do sail into combat with multiple ships, you can cut down on the chaos by controlling the lead ship and allowing the computer to control the rest