Sid Meier's Pirates! Strategy

While each game of Sid Meier’s Pirates! is unique, there are a few ways to maximize your visits in port:

If recruiting is an issue due to low fame, visit Pirate hangouts (where times are tough and eager crew are more plentiful)
Poor towns are still useful to unload excess cheap goods, such as food and guns
Less well-off towns can also provide better information – such as which ships are carrying specialists (Carpenter, Cook, etc.)
Many important upgrades for your ships are found in modest towns

Small settlements in particular are an oft-overlooked resource:

You can escort the mayor to become Governor of a nearby town, improving the local economy
One really devilish trick is to escort a Spanish mayor to a modest size town, then to sack it for even more booty
Though you can’t recruit in a small settlement, you can often trade for food and small amounts of goods there, even with normally hostile nationalities
Any traveler you meet there will often sell unique items (ruby rings) and treasure maps for big discounts
Be sure to dance with the ladies every chance you get – even at smaller towns – as they always have info or items to help you on your way

Major cities can be a formidable obstacle, but there are ways to circumvent that:

Sneaking in to the city lets you capture wanted criminals, and is a tense, fun mini-game in its own right
Having a set of lock-picks means you can take more chances when sneaking
In general, don’t hide for more than a minute or so, as the guards will tend to converge on your hiding place after that
Fellow pirates and native villages are happy to attack large cities, which softens them up for you
You can still capture the occasional pirate or native vessel, just do it in a different part of the Caribbean than where you intend them to assault for you

Broadsides and Boarding Parties

Generally, naval combat breaks down into when to hammer and when to board:

One of the first things you should do is to upgrade to Grape Shot, which targets enemy crew
Find out from the local bartender where to find Grape Shot
A good tactic with a smaller, maneuverable ship is to pound the enemy with Round Shot to reduce their working cannon, then switch to Grape to reduce the enemy crew, and board
In general, the only reason I use Chain Shot is when I want to destroy an enemy – dismast it first, then destroy it from afar
Along those lines, I generally sink Pirate Hunter vessels, unless it’s a Frigate, and I’m in the mood for one tough game
If all these seem a bit ruthless…well, you are a nefarious pirate, after all

Since much of the game involves sword fighting, there are a few ways you can go:

Master one blade and stick with that – if so, I recommend the Longsword
Try out all of the blades to see which one best fits your style – a reasonable approach

I tend to do the following:

Rapier = All duels with Captains of the Guard, Criminals, and the evil Montalban (who is quite good, especially on higher levels of difficulty)
Longsword = Default blade, quick enough to deal with most rapier-wielding foes, but strong enough to handle an enemy cutlass
Cutlass = Only for defense; since I’m offensive by nature, I rarely use this
Pay attention to what the barmaids tell you about the tendencies of your foes – it could save you a wound or two, and those add up over time
Also, get the Healing Herbs and the Incan Mystic Salve as soon as they are offered, even if you have to pay for them
Finally, any chance you have to get the Perfectly Balanced Rapier, take it! It’s sometimes offered after you catch a particularly dangerous criminal