Sid Meier's Pirates!

From Before I Play
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  • Bigger isn't necessarily better; smaller ships have smaller crews, which are easier to feed and keep happy. Small vessels are also highly-maneuverable in combat and travel the world map quickly.
  • When your crew has two or three thousand gold apiece as their cut, they'll stay permanently content and you can play indefinitely.
  • If you intend to complete the main quest or marry, do those quest chains before your character gets old and becomes a slow fencer.
  • A Ship of the Line is quite a rare ship. If you see one, or an unmarked large frigate that might be one, attempt to capture one. As good as small ships are, there's nothing quite like firing broadsides from SotL.
  • Unless you get a Ship Of The Line, only ever make sloops, sloops of war and royal sloops your flagships. In a sea battle, you want to get your ship into theirs as fast as possible without inflicting/taking too much damage, so a nippy maneuverable ship is your best bet. Only ever use grapeshot against enemy ships.
  • I usually take my starting sloop and camp out around some Spanish cities stealing trade galleons until they send a royal sloop out to get me. Don't worry about being outnumbered in sea battles, swordfighting is easy enough that you can be outnumbered 5-1 and still prevail.
  • For city battles, I usually try and equal or outnumber the opponents forces. Cover is your friend: Stay in the trees until absolutely necessary. That way cavalry are fucked against you and you take way less damage from gunfire. As soon as you have the manpower, start plundering cities. You get tons of cash, the battles are easy if you're sensible and if you install a new governor, that country will love you.
  • The best tactic to start out is to take a few trading ships, return to your base port and get promoted and repeat, until you are famous and wealthy enough to do whatever you want. I generally try and keep at least one nation on side at all times, just so I have safe havens to go to if I need repairs.
  • Download a mod to make dancing automatic. Dancing isn't fun or piratical, but it does get you some neat stuff.
  • If a barman tells you that a ship is carrying a carpenter/cook/whatever, ignore its nationality and attack it. The special crewmembers are really handy, and the odd ship here or there won't make a nation turn against you.
  • Working for the Spanish isn't worth the effort. They've got the most treasure/ships flowing through the Caribbean and they're almost always at war with one of the other European powers.
  • Seconding the sloop business. If you want to make ca$h money on captured cargo, just commandeer the galleons the loot came in and sell the leaking wrecks to the shipwright.
  • Unless you really need what they hawk, don't buy anything but treasure maps and gift jewelry from mysterious strangers. Dancing nets you the same helpful things.
  • The native charms and the religious artifacts (impress Indians and Jesuits, respectively) are broken and do nothing. Don't bother with those.
  • Yes, you're going to chase down Montalban and the other villains an awful lot. Keep at it.