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Way different gaming styles, I am afraid.
While I enjoy both, I am not so sure they would work together.
James, why the Shackles ? any reasons ?
Because "City State" is a pretty rough and tumble place, with an anything-goes element and an old-school Leiberesque vibe to it. Putting the city on one of the islands in the Shackles also isolates it. Not for bad reasons... but for good ones. It lets you treat that particular island as the "City State" island. I imagine that all of the dozens, if not hundreds of islands in the Shackles all have their own themes and plotlines.

Katerek |

The d20 version of CSIO is not a box, but a hardcover, going for around $30-40. If you're talking about the d20 Wilderlands of High Fantasy box though, the last I saw on ebay went for under $100.
I don't know how much the CS d20 hardcover is on ebay, but if you like the setting I strongly recommend it. Of all the d20 crap I had, it is one of the few things I have kept. Most of the rest I sold on ebay over the last three years.
The book was well done and stayed very true to the original material.
...come to think of it, my FLGS might have a copy. I will call him tomorrow and have him check, if he does, would you like me to encourage him to put it on ebay?

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Doing the reverse, my PF campaign is based in the Wilderlands. There's plenty of room there to drop almost anything in, including some bits of Golarion if you want them. I've added some Mystara countries to add more political options. Lots of space for classic modules if you like that sort of thing - I've run the 3e Necromancer conversion of Caverns of Thracia.

Dr. Johnny Fever |
I'd like to run a Wilderlands/CSotIO/Caverns of Thracia campaign with the Pathfinder rules. My gaming group is comfortable and happy with the Golarion deities, so I'm probably going to convert over the Judges Guild deities to the core PF pantheon. Here is the larger difficulty, however: is there any logical area on Golarion to drop a land mass the size of the Wilderlands, given that it is approximately the size of the Mediterranean Sea?
Thanks,
DJF

Jeff de luna |

I'd like to run a Wilderlands/CSotIO/Caverns of Thracia campaign with the Pathfinder rules. My gaming group is comfortable and happy with the Golarion deities, so I'm probably going to convert over the Judges Guild deities to the core PF pantheon. Here is the larger difficulty, however: is there any logical area on Golarion to drop a land mass the size of the Wilderlands, given that it is approximately the size of the Mediterranean Sea?
Thanks,
DJF
The only logical place - given its climate, size, and culture, would be in Casmaron.
Caverns of Thracia, of course, would be linked to Iblydos.

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I'd like to run a Wilderlands/CSotIO/Caverns of Thracia campaign with the Pathfinder rules. My gaming group is comfortable and happy with the Golarion deities, so I'm probably going to convert over the Judges Guild deities to the core PF pantheon. Here is the larger difficulty, however: is there any logical area on Golarion to drop a land mass the size of the Wilderlands, given that it is approximately the size of the Mediterranean Sea?
Thanks,
DJF
You might ask for some answers over on the Necromancer Games Forums they are the ones who released all that stuff for 3.0/3.5 and there are a lot of players over there who run this stuff with Pathfinder.