For context, i'm running a City of Greyhawk campaign, with a sandbox/players drive the plot style.
Probably the thing i struggle the most in my campaign is characterization. I feel most of the adventures we've had so far were "generic", like, we could easily have them in any other d&d setting. I want to give a clear "Greyhawksy" look and feel to this campaign, show my players why it's my favorite setting.
I don't know how to do that tbh. What would you folks suggest?
I'd suggest making a list of what you like about Greyhawk. You could get the Gygax book Saga of Old City and get an idea of what Gygax thought about the City of Greyhawk or listen to the annotated reading of SoOC here and I try to express what I like about Gygax's ideas for the Greyhawk campaign whilr I rad the book.
You could reread the Greyhawk material you have on hand and note down what you like. The heart of the Greyhawk feel is simply what you like and what inspires you. There are no wrong answers. The Greyhawk feel is simply what you like, what inspires you and what you create. There are no limitations.
Here are some contrasts to other campaign settings that make Greyhawk special to me.
1) High fantasy vs. low fantasy.
High fantasy worlds are full of magic. It is commonplace and seen by everyone most every day, though that doesn't mean everyone has access to it. Low fantasy means that magic is extremely rare and the world runs much like the real world from day to day for the common folk. Only the very rich and powerful have access to magic.
The Forgotten Realms and most other campaign worlds are high fantasy. High level wizards rule cities and run around casting flashy magic in battles for the citizens to see. Many businesses will have magic items used in their operation and the city Watch employs both clerics and wizards.
Greyhawk, on the other hand is low- to mid-fantasy (depending upon your style of play). Though the amount of magic available to adventurers in published modules would make it seem like a high fantasy world, commoners in the WoG don't generally see clerical magic except on special occasions and may never see wizardly magic in their life. Adventurers are special people, of course, so they tend to acquire more magic than the common folk. ;)
2) Points of Light
This means that the 'civilized' nations don't really control all the land within their borders.
The Great Kingdom may be vast, but the ruling family and each land-holding noble within its claimed borders are hard-pressed to control all the comings and goings of denizens (monsters) roaming throughout the land. Mostly, the goodly folk are clustered near cities and other strongholds and only well-guarded merchants and other well-armed groups travel the roads between.
This allows for adventures to be had most anywhere. If the land within each kingdom were free of humanoids, dragons, and other threats to the peace of the realm, the only place to find adventure would be the fringes of the map.
3) NPCs that don't meddle
In Greyhawk, there are many major NPCs that have their own concerns that generally don't involve the PCs. If you want to involve them in such, you certainly may, as the DM, but there is no reason to need to. The PCs are free to become heroes to rival Mordenkainen and Iqqwilv without needing to be beholden to either of them, or any other sponsor.
This also means that there is no super powerful global organization(s) that knows all and sees all in Greyhawk. The Circle of Eight is one of many wizardly cabals, but even its awareness of all that befalls the various nations and geographical locations within the Flanaess is extremely limited. Basically, each wizard in the Circle of Eight keeps close watch on his own backyard while also trying to be aware of any planet-effecting events, like an invasion by githyanki or the Blood War. However, Iuz initiating the Greyhawk Wars, their extent, and the betrayal of Rary all demonstrate that the Circle doesn't see everything and certainly doesn't have much control of what happens in the Flanaess.
Well, that's a short list that others are sure to add to.
I looks to me like the adventures offered in the City of Greyhawk box set seem kind of generic. I've never run this material. It's such an early 2nd Edition product that it name checks several 1st Edition products including WG7.
Maybe it makes sense to offer your players the same thing Gary offered his which is a chance to leave the city to adventure in Castle Greyhawk. I'd be tempted to offer the players WG7 the first time in and then WGR1 on the next visit (just based on the assumption that you're running 2nd Edition).
WG8 through WG12 are 2nd Edition products, so I'd be tempted to offer those Greyhawk-specific adventures to players or WGR1 through WGR6 and Ivid the Undying (which might be WGR7).
But then how much of a sandbox based out of the City of Greyhawk would it be? Probably not much.
"I'm just saying" it's called out in the City of Greyhawk material and Gary having his players move between the base in the city to adventure in the castle is what he did originally. Though I must agree that WG7 doesn't seem very Greyhawky either; it seems kind of insulting from what I imagine was Gary's point of view. Maybe WGR1 is in a lot of ways more Greyhawky, but then Zagyg and Castle of the Mad Archmage might be even more Greyhawky in some ways.
I posted a thread about 5 years ago called Define Your Ideal Greyhawk where people discussed the traits they go for in their ideal Greyhawks. It's too long to repost here, but you might find some useful information in it.
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