Dirigible
Explorer
In my head, the Isles are big, with more square miles of sea than land within the territory, so I don't necessarily need to map out the entire region immediately. I've got a good idea of where I want the PCs to start: a big port city called Tarantelle, on an island called Lucca, probably either in a tavern called the Buccaneers' Rest or nearby. (The PCs both have connections to a thieves' guild that runs out of the tavern.)
How to put together relevant bits of info here? I'm starting off by running a 1-2hr introductory vignette (probably no combat) to get to know the PCs a little, so what I really need is some NPCs, a rough idea of what the tavern looks like on the inside... and other stuff? What? Argh!
The Buccaneer's Rest
The husk of the clipper The Wavescythe lies in the middle of Dock St. in Tarantelle, looming over all the other nearby structures save the Mariner's Sodality guildhouse. Only the fore parts of the vessel survived the attack of the krakenspawn that seized her, and miraculously they remained afloat as it was towed back to port by salvagers. A wealthy former merchant-captain purchased the broken ship and had it dragged up onto dry land and built into a framework of walls and scaffolds, turning it into a nautically-flavoured building.
Renamed the Buccaneer's Rest, this rowdy tavern finds favour with sailors of all breeds. The floors, of which there are five, are shaped like half a boat - like a hyperbole, roughly. Each floor is larger than the one below, and have parts cut out to overlook the lower levels, including a balcony. Knotted ropes, ladders and dumbwaiters cross the empty space, allowing the bar servants to scramble up and down quickly, and stairs connect the floors for patrons.
Ground floor: Contains the bar and some nicely upholstered and padded seats for comfort, and the bar. Drinks are served in closed-top tankards, and the selection is relativly small; you've got a choice of grog, ale, grog, and a number of expensive vintage wines from distant islands, even from Mainland. This floor was once the bilge of the Wavescythe; uncharitable customers suggest the smell remains.
First, Second, Third Floors: Progressivly larger, these house the chairs, benches, tables and booths that service the majority of customers. They were once the belowdecks of the ship, and remain recognizable in appearence; wooden grills stud the ceilings and floors, beams from which hammocks once swung support the levels, and much of the furniture is made form old decking and barrels.
Fourth Floor: What was once the deck of the ship has become an exclusive, private floor for the more discerning customers. The furniture and decoration is suitably richer and nicer, and bouncers keep an eye on who can get in.
NPCs:
Gregor: A big, ugly man with mroe than a drop of Orc in his blood, Gregor is good natured enough to his friends and employees, but hard-nosed when it comes to business.
Bar Servants: Mostly young, limber, and phenomenally agile, the staff of the Rest are often recruited from the rigging rats of ships. Climbing skills are necessary to negotiate the complex off ropes and ladders that are used to get from floor to floor.
Marrensyrg the Magnificent: Once a magician of note from the island of Al-Vihari, Marrensyrg was found guilty of using his talents in the aid of criminals. The punishment for misue of magic in Al-Vihari is amputation of both hands. Stumpy, as he is known to the regulars of the Rest, is a tragic wreck of a man; unable to work magic anymore, he lives by his respectable skills as a storyteller, entertaining the Rest's guests.
And that's all I can think of at the moment. I second Morpheus' advice, though.