One way to rack up items quickly is to find an attractive daughter once you're a Colonel with that country (or have the French Chapeau) and interact with her repeatedly. To get items from an attractive daughter, you must get an OK dance, not a perfect one (which will give you information on Raymondo instead — useful, but you can already get that from Jesuits), so dance the best you can and, if your dance is going too well, intentionally fail to press a key near the end of the dance. Stumbling once at the end is sufficient no matter how well you're doing. So, when you find an attractive daughter, the sequence goes like this:
- Mediocre dance (one item)
- Ruby Ring (one item) — do not give the Diamond Necklace or you'll get info on Raymondo
- Defeat suitor (one item)
- Mediocre dance (one item)
- Get Mendoza and return her (info on Montalban, or a Lost City map piece if Montalban has already spawned or been defeated)
Each time, simply leave and come right back and until you've played out the whole sequence. (Decline the marriage proposal, though, since you need a beautiful daughter for a perfect score. Marrying a beautiful daughter also makes it easier to get Lost City map pieces.) So that's up to four items and Montalban info/a Lost City map piece for very little time and effort! Note that, when the daughter tells you about her suitor, you can revisit the governor and fight him immediately instead of leaving town again, saving a week of game time.
Note that if you already have many items, a mediocre dance, ruby ring, or defeating the suitor will likely give you a Wanted Criminal quest instead, and you will have to do the quest before you can get anything else from that particular daughter.
Any of the combat items are good choices. When a governor's daughter offers you an expensive item, choose the expensive item, since you may be able to purchase the cheaper item later for a low price.
These are of paramount importance. They extend your health, which broadens the window for when you can fight Montalban with a decent chance of winning.
Crew happiness items
These are great items to get, because you can last longer before you have to divide the plunder. Paying 10,000 gold for a Concertina is silly, though, because the gold is more useful in the long term for keeping your crew happy. If your crew is already unhappy, paying such an exorbitant fee for a Concertina can actually make them mutinous. Get them from governor's daughters or Wanted Criminals instead.
The Calfskin Boots are a good purchase, especially if you can get them very cheap. The Dancing Slippers are probably not worth the money if you are a decent dancer, though you may want to take them if a Wanted Criminal offers them. Once you marry someone, you can dance with her as many times as you like, so dancing skill is not a very high priority.
Ruby Ring / Diamond Necklace
You should get a Ruby Ring, partly so that travelers will offer other items instead (they will offer a ring very often if you don't have one). However, you can get one for about 1800 gold (assuming you're playing on Swashbuckler), so if the price is much higher than that, you can wait unless you really want to woo somebody now. Don't buy Diamond Necklaces, which are much too expensive to justify the expense, but you might want to take it if a Wanted Criminal offers one (especially if the monetary reward is small, like 1000 gold). Be careful not to give a Ruby Ring or especially a Diamond Necklace to someone who has already given you a Wanted Criminal quest you have not yet fulfilled, or it will be wasted.
The best person to give a Ruby Ring to is an attractive daughter, since you will get a choice of items.
The best person to give a Diamond Necklace to is a beautiful daughter, who will give you info on Montalban, or a Lost City map piece if Montalban has already spawned (or been defeated). Both are quite valuable. Giving one to a plain daughter will give you a choice of items. Giving one to an attractive daughter is the least desirable option; she'll give you info on Raymondo, which you can already get for free, and you can get an item if you give her a Ruby Ring instead.
French Chapeau / Ostrich Feather Hat
The higher your rank with the various countries is, the less useful these are. For example, the French Chapeau is useless if you're already a Colonel with everybody (though you can use it as a stepping stone to an Ostrich Feather Hat, which won't be offered if you don't have the Chapeau).
Dutch and Spanish Rutter
The Dutch Rutter will reveal many small settlements; the Spanish Rutter will reveal more. These are largely useless and should only be taken when you have a choice between this and an even more useless item. You will rarely need to seek a settlement except for Jesuits and Pirate Towns, and you can find these easily enough on your own. They might be decent purchases on lower difficulty levels, but are a waste of precious money on Swashbuckler.
Completely useless items
Do not buy items that improve relations with the Jesuits or Indians. These are the Golden Cross, Sacred Relic, Shrunken Head, and Carved Shaman Staff. They are completely useless because the Jesuits and Indians are always on good terms with you. This was not the way the designers originally planned the game: originally your relations were supposed to vary, but they had to release the game before they had a chance to implement this, and for some reason they left the items in.
Getting a perfect score on Swashbuckler
Before the game
You can start in any era, but things tend to be easier in the later eras thanks to the presence of more cities. 1660 and 1680 have a good distribution of cities from each country, whereas, in, say, 1600, the Dutch only have one city (St. Martin) that, since nearby cities like St. Kitts haven't been founded yet, is in the middle of nowhere. 1660 and 1680 are exactly the same map except Gibraltar is missing on the latter; the difference has more to do with things such as the frequency of pirate hunters, the types of ships used, and how much wealth each nation, city, and ship has.
Out of the skills, the Fencing skill is likely the most useful, since you'll be spending so much time fighting and you will eventually have to face the lightning fast Montalban. Navigation and Medicine are also strong choices, since Navigation will get you from place to place faster (especially when sailing against the brutal winds you'll find on Swashbuckler), potentially saving you years' worth of game time, and Medicine will broaden the window for when it's possible to beat Montalban. Navigation is particularly helpful in 1600, since there are so few cities. Gunnery is not a good choice unless you just really love shooting at ships, because usually you want to capture the ships near intact, thus getting their gold and goods, plus the price of the ship when you sell it. Wit and Charm is also not a good choice once you've practiced the dancing game enough, but it may be useful until then, since it is quite difficult until you get the hang of it.
During the game
First you'll need to assemble a decent crew. You'll want at least 100, since ships you capture will tie up some of your crew until you sell them, and 200 or more is even better. However, you're unlikely to get a crew of 200 in the beginning of the game. You just won't find many pirates in the towns.
To solve this problem, you can divide the plunder as soon as you have the opportunity to do so, so long as your crew will "eagerly" take their share (each pirate gets 50 gold or more). You'll find many more pirates willing to join you in towns, which should make up for the months you waste by dividing the plunder. When you try to divide, if they merely "gladly", "willingly", etc. take their share, cancel and go earn a bit more money or simply lose some crew in a battle (either a sea battle or land battle will do), since losing crew increases the average share per remaining member. You might not want to do something like take out Henry Morgan, though, because you'll get way more money than you need before dividing. It'll be more useful after dividing and help your next crew last.
Once you've got a decent crew, the number one thing to do is find Montalban. You only have so many years before you get old (especially before you've found the longevity items) and Montalban is an extremely tough opponent. Once your health is "poor" (which happens when you hit 34 if you have both longevity items and your special skill is not Medicine), you can probably forget about beating him. (Do remember that you'll regain some health if you purchase a longevity item, so hope is not lost if you hit poor health but don't have the items yet.) Once you've beaten Montalban at his hideout, it's all downhill from there.
A good way to get a lead on Montalban is to find and defeat Raymondo and repeat until you can rescue a family member. The family member will tell you where Montalban's ship is, and from there, barkeeps will usually keep you informed of his location if he's anywhere nearby. (Once you've defeated Montalban at his hideout, further family members will give you Lost City map pieces instead.)
That means your immediate objective when starting the game is to find Raymondo. The best way to do this is enter a Jesuit settlement; the abbot should volunteer the information. Once Raymondo has spawned, barkeeps should keep you updated on his location. (If you aren't getting any information out of the barkeeps, try asking around somewhere else, especially at or near his last reported location.) If the map piece isn't enough to find your family member, repeat until your map is complete enough.
Montalban's hideout spawns as soon as you beat him once, so by all means head straight there if you think you have a good guess as to where it is and you will have a large enough crew (you will need at least 200; 250+ is better).
Since Montalban and Raymondo (who is a frequent source of your leads on Montalban) sail in Spanish ports, it helps to be on friendly terms with the Spanish so you can enter their ports freely, since you will usually have to be near Raymondo or Montalban to get hints as to their exact location from bartenders. Note that playing for the Spanish doesn't have to mean fighting against the other countries; this is elaborated upon below.
Whatever you do, don't get arrested or thrown overboard. (This is not so vital if you just reload from the autosave when this happens, but if you don't like "save scumming", this is of paramount importance. Of course, it's also OK to take risks in the early game if you don't mind starting over if it goes wrong.) The former wastes valuable time and the latter causes you to lose all the gold you're carrying on top of that. To avoid this, take care not to start a fight with insufficient crew. If you don't know how many men are on the ship you're up against, assume a lot. Also, if you're attacking a nation's ships near one of their cities, assume a pirate-hunter will spawn — sometimes you get in trouble not with the ship you attacked, but with the pirate-hunter that spawns after it. If you do wind up in such a position, it may be better to let the pirate hunter fire away at you as you try to escape, since even letting a ship sink is preferable to being jailed or lost at sea. If you have only one ship, though, you'll be lost at sea if it sinks, so you might end up having to fight the hunter anyway in a last-ditch effort to stay in the game.
Of course, early in the game you might want to take some risks with the idea of just starting over if you get jailed or marooned, for instance to defeat Raymondo quickly or to get a better ship.
Pirate hunters can be troublesome, so how do you avoid them? The easiest way is not to get in fights with national ships at all. It sounds crazy and runs directly against the common wisdom of plundering the plentiful Spanish ships, but it's perfectly viable to simply never attack a national ship (Raymondo/Montalban excepted) in the early game and it won't damage your chances of a perfect score at all. Enemy pirate ships are fair game since they don't spawn pirate hunters. One trick you can do if you're not coming across enough pirates is to go to a Pirate Town and encourage them to attack a city. They will send out a ship that you yourself can attack. If you wait a bit before you do this, one to three Pirate Privateers should show up as well. (This is because the game thinks it's an escort mission, and escorting a ship always causes privateers to spawn. These Pirate Privateers won't do anything, though.) The Pirate Privateers might not be carrying much gold, but you might find their ships useful, and the reputation you gain for beating them all is quite useful. In fact, pirates make great targets exactly because you can advance your standing with all four nations at once. You can find lots of Pirate Towns (and usually a few named pirates) along the coast of Central America and Mexico if you're looking for action and promotions. As your rank advances, the nations will forgive you for taking the occasional potshots at their treasure and payroll ships, though obviously this will reduce your chances for promotions/land grants.
Happiness and dividing the plunder
The happiness of your crew depends on two things: how long you've gone without dividing and how much gold you have per crewmember. The longer the voyage or the less gold per crewmember, the unhappier they'll be. The unhappiness they experience due to voyage length, however, can be modified by crew happiness items (the fiddle and concertina each make the voyage seem four months shorter to your crew), and there is also a cap, so after about a couple of years of game time, the length of the voyage cannot make the crew any less happy. At this point, you will be able to keep your crew unhappy (as opposed to mutinous) if you have about 1000 gold per crewmember. So if you have 300,000 gold, you'll probably never have to divide the plunder again, because you'll never need more than 300 crew (unless you love trying to raid big cities). The only exception is if you can't find enough people willing to join your crew no matter where you go, but this seldom becomes a problem if you've already divided and each crewmember was "eager" to take their share (each gets 50 or more gold).
You'll want to divide the plunder as infrequently as possible, because it removes you from action for six game months, causing your character to age. In fact, if you're very lucky, you can get away with dividing only once (at the start of the game, to make it easier to recruit more pirates), so long as you get a steady supply of gold from named pirates, buried treasure, and especially lost cities (50,000 gold each) and Montalban (100,000 gold). However, don't fanatically avoid dividing the plunder either. You will need at least 200 (preferably 250 or more) to face Montalban at his hideout, and it makes sense to divide if you will be fighting Montalban soon but don't think you'll be able to maintain a large enough crew. Mutinies are also headaches, especially when they start stealing ships and taking some of your hard-earned gold with them. You can sell off all ships but one to avoid mutinies, but then you will be very vulnerable against powerful opponents like Raymondo and especially Montalban. It's best to always keep at least one spare ship and instead lose some crew through battle to avoid mutinies (since a mutiny is always caused by crew size — or hunger, but this is rarely a problem if you're careful), or divide if your crew is already too small to allow this.
Choice of swords
If you're experienced at the swordfighting minigame, your choice of sword doesn't matter much. For example, simply choosing the Longsword every time will do fine in most cases, regardless of your opponent or his choice of weapon. However, you may want to consider using a Cutlass against Montalban to counter his blazing speed. (This is assuming you are playing the 1.0.2 patch, where Montalban always wields a Rapier. Otherwise, Montalban will be wielding a Cutlass and you might possibly want a Rapier.)
Once your pirate's health falls down to "poor", you will likely need to use the Rapier to be able to attack effectively. Your defense will more than likely still be OK except against Montalban, though a strong opponent with a Rapier of his own will be quite difficult.
If you just pound the attack keys, you will lose very fast. The way to fight is to watch your opponent's move, then use the correct response, and attack if you have an opening after the response. You can sometimes take the initiative with a thrust against a stationary opponent, but only do this if they are slow due to low Advantage.
The High Chop and Low Slash seem identical at first glance — both will advance you two squares if they connect, one if parried, and none if dodged — but in fact they are a bit different. The low slash starts out slower, but the recovery is quicker. Hence, especially if your character is slow, it may be best to thrust at a low slash instead of hoping to jump and slash/chop back, or perhaps just jump and forgo a counterattack. If your opponent has the low slash skill, more than likely you can forget about doing anything about his low slashes at all. You should prefer using the high chop to the low slash, since you'll be using it when your opponent is overextended and so its longer recovery is not a problem, whereas the low slash's longer setup time might be. (You might prefer a low slash or a thrust against an opponent with the Fast Jump skill, though.)
If your opponent is very fast, thrust instead of chop. Better to advance one space than to screw up and be driven back two. If you're fighting Montalban, you can virtually forget about chopping unless you've slowed him down a lot.
Taunting is usually useless because you're typically better off using the opportunity to score a hit instead of tweaking the advantage bar. It may be worthwhile against Montalban, though, since keeping the advantage on your side will help keep him from becoming so fast that you just can't respond to him.
Choice of ship
Your choice of ship is very important. Attacking in a trade galleon, for instance, is never a good idea, because they're slow and not very maneuverable.
The combat ships are:
- Sloop class: Sloop, Sloop of War, Royal Sloop
- Brig class: Brigantine, Brig, Brig of War
- Combat Galleon class: Fast Galleon, War Galleon, Flag Galleon
- Frigate class: Frigate, Large Frigate, Ship of the Line
As you can see, each class has three types of ship, listed in ascending order of size and power. Generally, when you can, pick the third ship in your chosen class.
Which of these four classes is the best is a matter of taste, but it's generally agreed that the Combat Galleons are not as good as the other three.
Ships of the Line are exceedingly rare. You might never see one during an entire game.
Another interesting class is the Pinnace class:
- Pinnace class: War Canoe, Pinnace, Mail Runner
They are capable in combat, but the tactics you employ must be quite different from most other ships. With a Large Frigate, you can attack virtually any ship and get close enough to board before you take too much damage. But with a pinnace, you really must avoid getting hit if you can help it, since you are not hard to sink. Instead, your strength lies in your maneuverability, making it more difficult for them to hit you. If you're going to use a Pinnace, get a Mail Runner (either by starting as Spain in 1640 or by starting an escort mission for a declaration of war/peace and taking the ship).
It is quite difficult to capture a Pinnace of any kind on Swashbuckler difficulty, since they will be able to outrun you.
All other classes are useless to you and you should sell the ship as soon as you can:
- Barque class: Coastal Barque, Barque, Ocean Barque
- Merchant Galleon class: Trade Galleon, Royal Galleon, Treasure Galleon
- Merchantman class: Merchantman, Large Merchantman, East Indiaman
- Fluyt class: Fluyt, Large Fluyt, West Indiaman
Usually you'll want to use grape shot to reduce enemy crew without harming the ship too much. Be aware, though, that it has a limited range, and not all ships come equipped with it.
At higher difficulty levels, the wind direction and speed can have a significant impact.