Ahh this is a favorite subject of mine, my favorite part of worldbuilding. I think one of the most important things to decide at the start is the level and quantity of magic, both in terms of creatures and powers, items, forces etc. This is followed immediately by the age of the world, not just the age of the current civilizations but has it been around for several rises and falls. Next is connectivity to external planes, are these running in close parallel to the world where one can just find "weak" places and step right through into an elemental plane? Those sorts of places would definitely effect your geography and your populations, especially hostile planes. Also of importance at this step is the nature of the underground portion of your world, is there a version of the underdark underlying most if not all of your landscape? And are there portions in an older world where there has been collapses of the surface creating deep chasms full of not very nice things.
Depending on your magic content, populations can be fed with much less agriculture than in our own middle ages. There also would be a lot less disease and famine where there are divine magics to counter such maladys. This makes nice strong populations centers which you need because if there is strong evil out in the world then these are heavily fortified and magically protected so don't expect to have many outlying structures beyond a cities walls except where they can maintain their own defenses. There may not be roads connecting cities together, unless they can be adaquately protected in tracts of wilderness. Sea travel and commerce is even more viable because a ship can take its defenses with it in the form of strong magical barriers and wards, much more so than a man on horseback can. Beyond that there are many magical means of transporting goods and trades between cities. So your civilized areas may well be quite isolated, distant points on the map...unlike in our middle ages where population centers just grew outwards from initial settlements eventually ruralizing and connecting to one another. -In a fantasy world there are forces at play that prevent growth and expansion, territories of ravaging beasts, dragons, evil critters who live off of human and other races flesh. Things that would demolish and devour a full legion of well trained and equipped roman centurions, so conventional historical warfare as we know it may not even have developed in parallel to our history...those were fine to fight other countries and conquer many lands in our own history they were designed to fight people - it goes to pot quickly when an army of undead arises flanked by werewolves who can outdistance and take down your cavalry and lead by dragonmounted liches who can cut through a huge swath of the hardiest soldiers with a simple spell and then raise them up again to fight in their horde.
All of these things and more can have a bearing on what your landscape looks like. How has magic been used to alter the natural evolution of the geography? Where are the no-mans-lands, controlled by things that shouldn't be named? Where have druids been at work creating trees of enormous size and which forests and rivers are warded by dryads and sprites? Which mountains do dwarves call home and what have they done to them to say "keep out!" to any wouldbe tresspassers? Where have mages been working with earth elementals to build great barrier walls and rise up towering pinnacles of hardest stone to erect their sanctums on?
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