The following are a series of pillagings from my various folders, which may illustrate something about how I devise and run my settings, or may just be an excuse to look at some pretty medieval (mostly) things. Who knows?
The chronicle (yeuch) began with the fall of Constantinople to the Fourth Crusade; theoretically that's twenty-five or so years before the setting date for Dark Ages Vampire, but screw that - why start after the world-shattering cock-up when you can drop players right into the middle of it, have them lose everything they hold dear, and then casually slide in with "oh by the way you're a vampire now"?
I'm a big fan of vaguely medieval maps, too, at least for showing to players. It's a gesture that has a certain verisimilitude about it - modern, Ordnance Survey style maps with grids and scales lead to a sort of modern way of thinking, whereas this kind of thing sort of... grounds people in the moment. This one creates the illusion of a crowded, crammed city, without being overburdened with details or crowding out the larger features (I can easily spot the Hagia Sophia, Hippodrome, Mese, Varangian Palace, dockmaster's mansion, Jewish and Latin quarters, and all the ways in or out - and that's all that's really needed).
I do use more modern ones with things like gradients and all the churches and distances staked out for planning - this one is the in-game resource. Among its other virtues, incidentally, is its resemblance to the hyper-detailed map from Sold Down The River, which is one of my favourite RPG supplements ever and one I wish I'd kept hold of during the Great Nerdstuff Purge of '08.
The refuge of Lacadaemonia. Just imagine that the land you can see in the background is water, and you'll get there. On this one small slice of land in the middle of the Med, Cainites are safe; they're not obliged to conceal their nature, and they're encouraged, nay instructed, to leave their politicking at the door, on pain of having a pair of Brujah jump up and down on their faces.
Sometimes, of course, the guest is a half-crazed Toreador Methuselah who's recently done diablerie par exellence, is also a closet infernalist, and who will not take "get out or be stomped" as an answer. Isabelle Adjani has exactly the right kind of haunted, fragile-yet-powerful beauty I wanted Mary the Black to have.
(Yes, she's a Toreador in my setting, because thirteen clans is quite enough and I prefer infernalism as a purely cultural practice. If this bothers you, I'm sorry. I also abolished the Ravnos because I hate Chimiestry... Chimerastry... that stupid reality-warping discipline. The Laibon are my thirteenth clan. I'm sure I've committed other blasphemies against canon at some stage.)
Varangian soldiers. Apparently there were, effectively, expatriate Vikings in Byzantium. I can roll with that. The Varangian Guard's keep in the north of the city is a desolate symbol of the Latin conquest, haven to a powerful Nosferatu, a resonant site for our Brujah (who's of Varangian descent himself) and will one day be the centre of resistance against the usurper Prince.