History YMMV / SidMeiersPirates

* AngstWhatAngst: Your family members push aside the fact that they've been captured and enslaved to tell you about the lost Inca treasure.

* SequelDifficultyDrop: The 2004 game is much more forgiving than the earlier ones. The sheer variety of upgrades you can acquire for your ships, your pirate, and your men can mitigate the effects of aging and declining crew morale, the new sword-fighting minigame gives you a ton of tactical maneuvers that can make up for your atrophying abilities, crew desertions aren't nearly as bad, you have more opportunities to track down lost relatives than by getting your leads from promotions, the turn-based land battles make city raids safer and more profitable, and you have a greater (and more visible) hand in building up the wealth of the nations you support.

* DemonicSpiders: The Cavalry in the old games' land battles. Whereas they can be manageable in the 2004 version, as long as you have plenty of forests to cover you, they have no real weaknesses in the earlier titles, and can easily rip your units to shreds once they get in range.

* DesignatedVillain: The game practically ''encourages'' you to attack the Spanish. As noted on the main page, on the default settings the Spanish have the most plunder and the least ability to defend themselves from attack by pirates. Furthermore, all three plotline villains (Montalban, Raymundo, Mendoza) sail under Spanish flags, meaning that anyone going for OneHundredPercentCompletion is going to have to attack Spanish military ships multiple times.

* ThatOneLevel: Not a level per se, but the westernmost section of the map, in the region of Mexico, is the least popular area to be in. Getting out of it is always a long and trying process due to how the winds blow. Worse, there are only a handful of cities, and all of them are Spanish. Heaven help you if you end up here with a Spanish bounty on your head. That said, Vera Cruz and Campeche do have quite a bit of loot for the taking, which can make venturing into this region very profitable, if risky.

* ThatOneLevel: Not a level per se, but the westernmost section of the map, in the region of Mexico, is the least popular area to be in. Getting out of it is always a long and trying process due to how the winds blow. Worse, there are only a handful of cities, and all of them are Spanish. Heaven help you if you end up here with a Spanish bounty on your head. On the other hand, depending on the version, Vera Cruz and Campeche do have quite a bit of loot for the taking.

*** The same cannot be said for Colonel Mendoza (the one who kidnaps the governor's daughter), who does not appear after being defeated, meaning the player most likely executed him.

* SurpriseDifficulty: Playing at any of the four (originally three) lowest difficulty levels isn't terribly difficult. Sure, Rogue (the second highest) is hard, but it's not impossible. But when you're no longer satisfied with a scant 30% of the plunder, you decide to bump it up to Swashbuckler for that 50% share and discover you have entered ''Hell itself''. Storms will rip your ships apart when before they did little damage. The captains of Mail Runner ships (the smallest, least defended ship) will fight as if they were captaining a fleet of Brigs. Land combat, previously difficult, will become nigh impossible. The wind will change constantly, and ''always'' against you in naval battles. Swordfights will become a test of luck rather than skill, as apparently everyone you cross swords with trained specifically to defeat ''you'', and [[BigBad Montalban]] becomes [[{{Unwinnable}} nigh-invincible, if not]] ''[[{{Unwinnable}} completely undefeatable.]]'' Suffice to say, Swashbuckler difficulty is excruciatingly hard, never lets up, and makes sure you ''earn'' whatever ending you get.

* MostAnnoyingSound: The sound of the alarm if you get sighted while sneaking in and out of cities. Not so bad on its own, but if you play on the highest difficulty setting and try sneaking around, you will likely hear this a lot.

* CrowningMomentOfAwesome: The barmaid's GrievousBottleyHarm when you defeat the Annoying Captain.

* MostAnnoyingSound: BONGLE BONGLE BONGLE BONG. (This is the sound of the alarm if you get sighted while sneaking in and out of cities. Not so bad on its own, but if you play on the highest difficulty setting and try sneaking around, you will likely hear this a lot.)

** Instead of taking Montalban or Raymundo prisoner and interrogating them for information of lost family members, the player is just content with a map piece and repeating the process of finding them again.

* ThatOneLevel: Not a level per se, but the westernmost section of the map, in the region of Mexico, is the least popular area to be in. Getting out of it is always a long and trying process due to how the winds blow. Worse, there are only a handful of cities, and all of them are Spanish. Heaven help you if you end up here with a Spanish bounty on your head.

* SurpriseDifficulty: Playing at any of the four (originally three) lowest difficulty levels isn't terribly difficult. Sure, Rogue (the second highest) is hard, but it's not impossible. But when you're no longer satisfied with a scant 30% of the plunder, you decide to bump it up to Swashbuckler for that 50% share and discover you have entered ''Hell itself''. Storms will rip your ships apart when before they did little damage. The captains of Mail Runner ships (the smallest, least defended ship) will fight as if they were captaining a fleet of Brigs. Land combat, previously difficult, will become nigh impossible. The wind will change constantly, and ''always'' against you in naval battles. Swordfights will become a test of luck rather than skill, as apparently everyone you cross swords with trained specifically to defeat ''you'', and [[BigBad Montalbon]] becomes [[{{Unwinnable}} nigh-invincible, if not]] ''[[{{Unwinnable}} completely undefeatable.]]'' Suffice to say, Swashbuckler difficulty is excruciatingly hard, never lets up, and makes sure you ''earn'' whatever ending you get.

* SurpriseDifficulty: Playing at any of the four (originally three) lowest difficulty levels isn't terribly difficult. Sure, Rogue (the second highest) is hard, but it's not impossible. But when you're no longer satisfied with a scant 30% of the plunder, you decide to bump it up to Swashbuckler for that 50% share and discover you have entered ''Hell itself''. Storms will rip your ships apart when before they did little damage. The captains of Mail Runner ships (the smallest, least defended ship) will fight as if they were captaining a fleet of Brigs. Land combat, previously difficult, will become nigh impossible. The wind will change constantly, and ''always'' against you in naval battles. Swordfights will become a test of luck rather than skill, as apparently everyone you cross swords with trained specifically to defeat ''you''. Suffice to say, Swashbuckler difficulty is excruciatingly hard, never lets up, and makes sure you ''earn'' whatever ending you get.

* ThatOneLevel: Not a level per se, but the westernmost section of the map, in the region of Mexico, is the least popular region to be in. Getting out of it is always a long and trying process due to how the winds blow. Worse, there are only a handful of cities, and all of them are Spanish. Heaven help you if you end up here with a Spanish bounty on your head.

* DesignatedVillain: The game practically ''encourages'' you to attack the Spanish. As noted on the main page, on the default settings the Spanish have the most plunder and the least ability too defend themselves from attack by pirates. Furthermore, all three plotline villains (Montalban, Raymundo, Mendoza) sail under Spanish flags, meaning that anyone going for OneHundredPercentCompletion is going to have to attack Spanish military ships multiple times.

* CrowningMomentOfAwesome: The barmaid gets one.