I can imagine that it is a big and bussy port. Enough place for some shady dealers and pirates. However, the comparison with Île de la Tortue was a little extreme, as that would make it an anarchic pirate island.
There were never any pirate RPs in D'Hara, or RPs about criminals of any kind. The first age was a kind of dark era, one of struggle, strife, and unstable autocratic regimes. Hard times for all who lived on the isles. As D'Hara grew, it gained newfound prosperity. The end of the war with Caerwyn and Madina resulted in the start of a golden age for the duchy of Paisly, and coincided with Verdis Elementum taking over almost all of the isles, the monarch becoming more withdrawn and Dragon Worship but a folklore of the royal family. A new D'Hara was emerging, and was crystallized when the Dragon King abdicated, allowing the formation of the lords' Republic with little interest in new feuds, being tired of all the ones they suffered, and investing itself in trade more than ever. I really do see modern D'Hara as italian-like.
However, not all cities in D'Hara are the same. Paisly, the "newborn", has reached full production and generates a considerable amount of wealth, and since not that long ago. When Machiavel left Paisland for Paisly, the latter had but recently started to produce more gold than the former. Port Raviel and Port Nebel, the core and historical cities, have not been so lucky and have had the populations decimated by starvation on many occasions (resulting in various revolts). I'd say these are rougher neighborhoods than what you'd find on the continent, but still not pirate-like.
