The culmination of the Heileen series, Heileen 3: New Horizons has the heroine of the series, Heileen, rescued from a shipwreck by a band of oddly sympathetic pirates. This game follows her journey as she tries to locate her other friends and relatives, while having the freedom to have a say in her future, whether it is pursue a romance from one of 8 possible people, or whether she finds contentment in a future career.
For how the game runs, it is reminiscent of visual novels (which the first two of this series actually was) with some dating sim mechanics thrown in. I appreciated actually having more of a say in my character.
I liked the game, but there are some caveats. First thing many people comment on is the price. This is on the higher end of the spectrum, but the Steam version contains both the GirlxBoy romances, and the GirlxGirl romances (which can be bought singly on the developer's website.) However, the developer does run several sales through the year if price is a concern.
Before purchasing, I highly recommend trying the demo (from the Dev's website as well). This style of game is certainly not for everyone, but the demo definitely gives a good idea what to expect.
Additionally, I would be remiss not to mention the job skills. It gets really grindy to raise those levels; additionally to unlock the final job endings, there is a Sin/Virtue system in game which must be met as well.