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How many miles of land would you need for 3 smallish human kingdoms, a LARGE red wood forest elf kingdom, a horseclans style kingdom, a mountain dwarven kingdom, and a large swamp lizardman kingdom.
All this on a massive hilly roling plains bordered on 3 sides by HIGH mountains and an ocean on the last side.

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It depends on what you mean by kingdom. Do you mean like ancient Ireland, where a kingdom is a hillfort and the surrounding farmlands, or a kingdom like Imperial Russia?
If each small kingdom is about 2-3 days journey across, and the large ones maybe 5-10 days journey across, then the whole shebang would be maybe 16-20 days across depending on how you clump them.
Now figure a day's travel on foot is about 25 miles. The region would be around 400-500 miles across. Assuming it's oblong, maybe 200-300 miles wide. Take the medians of those ranges, 450 miles x 250 miles, and you get 112,500 square miles.
For comparison, Ireland is 32,595 square miles and the UK is 94,060 square miles. So my numbers above are probably too high. But there's a good starting point for thinking about it.

GermanyDM |

Take a look at http://en.wikipedia.org/wiki/States_of_the_German_Empire to see how the former, former, former German empire was divided. If you remove the various provinces of Prussian and Alsace-Lorraine from the map, you get a close approximation of how the current boundaries of Germany were then divided into 25 different political regions, including enormous ones like Bavaria and Baden-Württemberg, which are easily larger than many modern European countries.
I'd use Switzerland as a closer example. 16,000 sq miles. 126 miles to a side. 26 cantons that could easily represent kingdoms. That makes it perhaps 3 times larger than you need.

R_Chance |

How many miles of land would you need for 3 smallish human kingdoms, a LARGE red wood forest elf kingdom, a horseclans style kingdom, a mountain dwarven kingdom, and a large swamp lizardman kingdom.All this on a massive hilly roling plains bordered on 3 sides by HIGH mountains and an ocean on the last side.
Feudal medieval kingdoms can be fairly small or fairly large :) An old 3PP 3E book (with a lot of research behind it) "A Magical Medieval Society: Western Europe" classed a small feudal kingdom as roughly 6,250 square miles or 79 x 79 miles. A large feudal kingdom could go up to 360,000 square miles (600 x 600 miles). Population density from 30-160 adults per square mile. That would depend on geography, fertility of the land etc. The assumption for population was roughly 1 million (small) to 10 million (large) people although that doesn't quite fit the sizes they give (unless you assume small kingdoms have more fertile land as a proportion of their space than large which might contain swamps, mountains etc. with very low populations). Then again that's probably total population vs. the adults per square mile...
I had my PDF of Magical Medieval Society handy, but not my, even older, Chivalry and Sorcery (1st edition) supplement that had feudal kingdoms, horsed nomads, etc. in it. I haven't spent a lot of time with the old C&S since I picked up the dead tree and PDFs of A Magical Medieval Society... to bad. They had detailed information on feudal society, highlander stuff, Vikings, and horsed nomads. Pretty nifty iirc. They were history buffs writing the original C&S. It certainly showed.
Additionally I would assume the carrying capacity of swamps, mountains and forest to be significantly lower than good farmland, so depending on the numbers of Elves, Lizard men and Nomads your planning on they could vary from small to really big...
Have fun with it.
And if you want detailed information on feudal society in a fantasy game, the PDF of A Magical Medieval Society: Western Europe is probably still available on Paizo (I picked up my second edition PDF here a while back).