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I’ve played this game for a long time, left for about 4 years, and now come back again. It’s fun!

The following doesn't give you tips on how to do each process like sailing, sword fighting, dancing, or sneaking. This is an overall strategy to get your to early retirement at the peak of your life.

You want to complete as many of the goals and maps and treasures as you can at the youngest age you can. This generates elevated rank, gifts, and suggestion. From all sources. There is a trick to timing this process.

As the game starts grab the fastest boat you can - an Indian canoe. If you start with anything else, even a Royal Sloop, dump it and get a canoe. If anything, work your way up to a Mail Runner and stop there. Load all the shipwright items you can. You’ll keep this for the first ½ of the game.

Speed is criticial in the beginning. You don’t need many men. In fact, you can retain a minimum of sailors for one thing, boarding and fighting. Your sailing skill will be to NOT cannon fight, but to board as fast as you can. That way you need less in repairs and your captured ships are worth more. It’s you who are the leader/fencer. Do it well and you’ll always win. Learn to react to your opponents first move to block, then deliver your shot.

Your only job of fighting is the guards blocking the barmaid and barman AND ship captains. Your goal in each section is to gather a single piece of a map, lost family member, or Montalban’s fort location. Once you have gathered those do a save game to come back to. Now you have free time to do anything else. This is critical. This save will lock in all the pieces of the maps, quests, landmarks, etc. shown so far. From this point on your sole action is to find the rest of the map pieces AND sail around to mark all the landmarks on the map. They will become critical for finding treasurer, forts, hideouts, etc. on the pieces of maps you do get. Many times I can find the treasure or house with a single map piece because I recognize the landmark along the shore line and can work it out from there. Don’t bother to dance with the daughters unless you want the practice. Don’t buy items from the tavern traveler unless he repeatedly only offers them and needs a nudge to sell another map piece. Everything you get will be lost as soon as you reload your previous save. Don’t go after treasure fleets, payroll ships, or anything else. You want to stay on good terms with everyone, find all the treasures, your relatives, and Montalban’s fort.

Once you are ready to knowingly find everything in this phase you want, write down the maps because they will be lost too. Now go back and load you previous save when you were just starting out on this set of quests. By starting over, you reset the clock, find everything in record time, drive for a single piece of each map again and save again. During this short interim phase from the save to the first map piece, dance, buy, or acquire all the items you can until you’re ready to save again. They stay with you when you come back. Do this again and again and you will ultimately end up with everything completed by the age of 26, You will, also have a map of all the landmarks around the Carribean for any further hints they give. A great time to save is when you have one piece each of a treasure, lost family member, and Montalban’s fort.

Do NOT kill any of the pirates you find. Mark their locations for later. When you reach a point where you need to divide the loot, sell everything, including the cannons, except the hull of the ship you want to keep. Cannon and food will be restored. Do this in the same process as above. The only thing you want to divide is the loot and treasure money you’ve collected. Save killing the pirates until almost the end for a huge amassing of money to retire on.

When you have Montalban’s fort left, now is the time to get bigger ships for lots of crew for land battles. After he’s captured, decide where you want to retire (beautiful daughter). Conquer the city and give it to another nation. Keep track. Leave the city and attack again and again and again. Each time give it to a different nation until you are the highest rank in all of them. You’ll collect all the items in the process.

Do one final division of loot. This does a couple of things. It gets rid of a lot of excess crew, gives a 6-month hiatus for hot headed nations to cool down, and now lets you go after all the pirates at once just before you retire for good.

Now is the time for some fun end games. Try to conquer and convert all the cities and towns to a particular nation. Try exploring hidden areas were nothing else seems to be. Go to Puerto Principe and Panama since these are overland treks and seldom done. Finally retire at a relatively young age, in good health, fabulously wealthy, with vast lands, a title, and a beautiful wife.

One thing I do before I start is print out a two page map of the time period I'll be in, usually 1660. I circle the cities with beautiful daughters, list the shipwright skills, put an X at pirate lairs, circle them for named pirate leaders,and put a dot with a leading line to more space to write in shoreline markers.
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