Reach the rank of Count with any nation and go into ship battles with any desired ship. Damage it a lot but don’t make it explode. Keep the ship and head to a port where you are at the rank of Count or higher. Talk to the shipwright to get free repairs. You can repair a damaged ship for free and sell it for much more.
At the start, when you are a young swashbuckler, doing quick strikes with the cutlass is the best way to win sword fights. Later in the game, as you get older and have slower moves, start fighting more defensively or improve your chances by using grape shot on the opposing crew before entering hand-to-hand combat.
One of the most important features is "Caribbean Politics", which can be seen your personal status sheet. This shows which countries are at war against each other. Always wage war against country that have the most enemies. For example, if the Spanish are at war with the French and the Dutch, its politically easier to gain military rank if you fight the Spanish instead of the French and the Dutch. Fighting more ships and plundering more cities also provides more "acre" bonuses each time you gain rank. Keep in mind that this tactic depends on the situation of Caribbean politics and economics. Using the same example, if the French and the Dutch are wealthier, it might be better to wage war against them instead. They'll have more ships sailing compared to a country that has weak and less cities or towns. When waging war against a country, don't always plunder a city to the brink of poverty since this will mean less ships to attack. Try changing the political powers of certain Caribbean regions by capturing cities and giving them to nations that don't have a city or town in that region. For example, in eastern seas (around Martinique), the Spanish have no town. The closest is Trinidad (south) and San Juan (north), but none in the middle. Giving a city or town to the Spanish in that area may prove beneficial for future political wars.
Search for the "St. Eustatius" entry in the Piratopedia. Notice that the word "Eastern" is used, but only the "Easter" part of it is a hyperlink. Click it to see a hidden page that denies the existence of any Easter Eggs in the game.
Land battles are hard to win, even if outnumber the enemy. The key strategy to remember is to hide in the trees since soldiers attacking your troops in the trees will have less than a 20% chance of inflicting critical damage, and all damage is divided in half. Also, keep an eye on your morale. Low morale means your troops might run away. Always enter battle with about one quarter more troops than the city guards. You can also weaken enemy ports and cities by using the Pirate Havens and Indian Villages. The Indians or Pirates will attack the town and make the town lose guards, whether or not they win the battle. This also makes the city lose wealth, however. If the city was once "Prosperous" it may go down to "Poor" or "Modest". You can always alert the missionaries in the Missionary Camps and tell them to travel to the city you want to become wealthier. You must attack cities at the correct moment since too long after sending in missionaries may result in more guards accumulating than before. You should wait only two to five days. Get your buccaneers to the front lines and have your pirates and officers get into position for flanking. Send more than one group of pirates against one enemy in case the enemy moves. Before you attack with your pirates, attack with your buccaneers by holding [Shift] then selecting "Next Turn" from the control panel. This should either kill or significantly damage the soldiers. Be sure to search for a hill to flank the enemy from. With this strategy you can easily defeat an enemy that’s only five or more soldiers weaker than yourself.
When battling other ships, get in front of them and have them chase you. Then, when your guns are fully loaded, turn, fire, and straighten again. Repeat this method until you wish to board or they surrender. It’s recommended you use grape shot or chain shot.
Unlock the listed ships by performing the corresponding tasks:
SHIP - HOW TO UNLOCK Ship Of The Line (Frigate class) - Relentlessly attack shipping of the English, French, or Dutch and keep watch for a "New Warship" (Ship Of The Line) sailing around. Royal Sloop (Sloop class) - Often seen as a Pirate Hunter out of Spanish ports. Attack shipping around a Spanish port and one may come out to attack. Brig Of War (Brig class) - Often seen as Military Payroll carriers, or Troop Transports. They attack as normal, but beware of large amounts of enemy crew. Mail Runner (Pinnace class) - Offer to escort a war declaration or peace offering from a colony, then attack the courier once out of port. Large Frigate - Henry Morgan has a Large Frigate. Boarding his ship leads to a fairly easy sword fight, even under the Rogue difficulty.
-Food, goods, spices, luxuries, and sugar can keep your crew happy, but it's hard to keep a good amount of them on hand. Upgrade a good ship and then get a treasure ship since they carry a lot of cargo. Keep two ships permanently and sell the others. Keep a battle ship and your larger ship to carry supplies for long voyages.
-Certain special items in particular decrease the unhappiness of your shipmates. Items such as musical instruments are excellent for long sea voyages. Get these items from the Mysterious Traveler at the pub or from Governor's daughters. There are also many people in the Caribbean which will decrease the unhappiness of your shipmates. The cook, for instance, will provide better meals while the quartermaster will enforce discipline, etc. To obtain these special mates, ask the local barmaid for more information on the ship carrying them and attempt to capture those ships. Just because they're unhappy doesn't mean you have to retire soon. You can push the crew to their limit even though their status is "unhappy". However, when they are "mutinous", you're in trouble. Always balance your cash reserves with your crew size so you can sail for more than two or three years without having to "divide the plunder".
Below are the different types of cities followed by a description. Note: Poor defenses and weak defenses aren't the same. Poor defenses are worse than weak defenses.
CITY - DESCRIPTION Capital Cities - Large and wealthy with strong defenses. Port Cities - Large and wealthy city with weak defenses. Towns - Large and poor with strong defenses. Colonies - Large and poor with weak defenses. Trading Posts - Small and wealthy with strong defenses. Strongholds - Small and poor with strong defenses. Villages - Small and wealthy with poor defenses. Outposts - Small and poor with poor defenses.
When you receive the hand signal from the Governor's daughter, select the button for the hand movement just after she gives you the signal. You will do a special dancing move, which will get her heart up quickly. If you do it many times in a row and her heart is big enough when the mini game is over, instead of kissing her hand you’ll instead spin her around and she will then kiss you. Afterwards she will likely give you a present or valuable information.
When escorting ships, you'll almost always be intercepted by three opposing enemies, prompting a "sea battle" on the main political sea map. To avoid this, attack the ship you're escorting and when you enter the combat screen, sail away from the ship to flee. Usually, the other ship will sail in the opposite direction. After you exit the combat screen, the escort ship will have sailed a long distance. If you are close to the destination, the ship you are escorting should arrive automatically and complete its mission. Note: This doesn't work well if the target destination is still far away.