I wanted it to be something like Dave Arneson's Blackmoor: fairly geographically limited but conceptually large enough to house the bizarre mixture of Hammer Horror, 50s sci fi, Clark Ashton Smith, Tolkien, and Vance I enjoy. At this point, I've more or less decided that the Dark Country is my setting. So it's the one I'm most focused on tweaking at the moment.
One thing that attracted me to my Cuccagna idea was the presence of water. I remember really liking how much water was on the old Wilderlands maps because it gave them a very Sinbad the Sailor sort of vibe. The PCs might come ashore on a small island that has a bit Harryhausen-style golem on it or something else cool. However, my two big settings - the Dark Country and Uz - both lack a large amount of water. So I decided to add some.
Dave Arneson based his original map of Blackmoor on a map of the Netherlands. I thought I'd do the same thing, but with a different region. The Proto-Dark Country game originally took place in an analog for the Baltic, but I didn't like how flat the region was so I later changed to Romania. Well I decided yesterday to look up some maps of the Baltic - since it's a sea and obviously would have water - and I found this:
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Almost immediately I noticed that the forest in the southeastern corner of the map had a fairly similar shape to the Carpathian Mountains. At that point I decided to combine the two. This is the result:
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The astute observer will note that the southeastern quarter of my map is more or less the same as the one I worked up in April. This is intentional as it represents the parts of the setting that have actually seen any amount of play. The other quarters are still subject to change, especially the southwestern one, but this gets across the general idea I think.
Note that the newly added sea already existed, I just shifted it a bit from its original position. It's called the Starry Sea, and here are some notes I worked up for it several months ago:
The Starry Sea is actually a large, deep lake that formed when a glacier melted several millennia ago. Strange lights occasionally stir in the deeper waters, and few sailors will willingly cross it from end to end.
Not sure if I'll be sticking with that, but there you go.
I'm still working on the theoretical structure that ties all of my influences together, but I'm definitely happier with the map.