Now to be fair, I really should give each of these games their individual credit. You will quickly see the similarities when you start playing them, with trading and boat building as well as career advancement and expanding your wealth. But, there are subtle differences between each I would like to point out. None of these games are simple. They hearken back to a day when you didn't just play for a few seconds to get ahead.
Patrician III: Rise of The Hanse
This game is played during a pivotal time in history, during the rise of the Hanseatic League. Your reason for being is to be eventually elected the Alderman, or head of this league. It is all about your reputation. Do whatever it takes to make sure your people are happy and your town is protected as well as your standing. Should this include piracy, then so be it. It takes one to find one, yar! But, you can also rise up as a noble trader as well. This game is about keeping everyone happy all the time.
Tortuga: Pirates of the New World
Now this one is more my style. More of the actual ship to ship combat we have come to know and love. Board or be boarded as every man on deck counts in a battle. Grow your fleet and overpower your enemies. Triumph through epic ship battle to seize lands in your countries' names and increase your wealth. However, there is a catch. Only the Governor of a town can loose you upon the next town; therefore, you have to be in good standing with him. And if you're lucky, along the way, you may even find the woman of your dreams.
Port Royale 2: Cartels, Constructions & Conquest
Bringing it all together from the other two titles, Port Royale 2 is the newest of the three games. Released in 2004, it is a very good blend of city building and swashbucklery. This game is a little more open-ended, allowing you to create a vast empire of trade routes. You must annex towns to gain control of them. Once you annex a town, you have the ability to open your own industry and become rich beyond your wildest dreams.