The Campaign Builder's Guild

I have been wondering how to construct the map for my setting.
The geopgraphy as it is now is sort of blurry, with no definite areas. Or well, I have some regions in mind but I need to find out how to fit them together.
My sketches seem to resemble each other and my geographic ideas have stagnated, so I need some fresh interpretations.
So I thought I might ask you for ideas. Or even better, sketches! I know some of you are quite good at this stuff after all. Doesn't need to be fullfledged maps, just some shapes and notes to help my stagnated mapping creativity along.
I mostly just want to get the overall layout of the map. The details I can fit in later.
I don't know if a landscape or portrait map is preferable. Style-wise I'd probably wish for a mix between authentic-looking and fantastic. Brown parchment-ish with muted colors. But that shouldn't have too much effect on coastline design'¦
I think a map tells a lot about a setting, so I'm pretty picky when it comes to coastlines and such. They should appear plausible, yet be "exciting" and interesting. The shape of the continent should generally convey adventure and such, as far as possible :P (yeah, that doesn't make a lot of logical sense really, but I'm sure some of you can understand what I'm talking about; some maps are interesting, some are dull).

There are a few things that should be taken into account but feel free to interpret them however you want to get something out of it! I have left the details slightly vague to that end.
-Besmakia is the main continent. It's central/eastern Europe inspired, but since most of that is landlocked (which Besmakia as a continent probably isn't), it might be hard to draw inspiration from that.
-Itelghast lies north of Besmakia. It should probably border the arctic circle, but should be somewhat hospitable.
-Ieshyn, the southern continent, should probably be an offmap continent somewhere south of Besmakia.
-The Whisperlands should be as far north as possible (possibly offmap) and have access to the the arctic ocean as they hunt whales.  
- the Winter Channel and Kolyaev. A channel passing by Kolyaev, and separating two large landmasses. Probably connects an outer sea to an inland sea.
-The Summer/Halegate Channel. A not-yet-build channel that I have had a lot of trouble placing. The key is that it should be profitable and annoy the hell out of Kolyaev as trade will go the other way around.
-Umber Valley/Soot corridor: a large central river-valley that spills out into one of the seas. Carries trade down the river from Ferzest. Should be nested between mountains and forests.
-The Umbilical. Can possibly be left out depending on map, but the idea was that this isthmus connects Besmakia and Ieshyn.
-Besmakia should have some swamplands where the temperature is closer to temperate.

Trade-wise there are some few considerations (if you want to place the Halegate Channel the optimal place)

-The Whisperlands produce Ambrosia, the most valuable spice in the world.
-The Union (Ferzest) produces massive amounds of iron and iron products. These are shipped down the river Umber (the Soot Corridor) to be ferried away and traded.
-Ieshyn is a very profitable trading partner with a lot of exotic goods.

I know this is an odd request, but I hope some of you will help me. Or maybe see this as an interesting challenge.

Since you're working with coastlines as one direction to building your setting map, I try to think up specific location areas for various parts of the coastline if not all of it. Your isthmus is a good description of one of them. I try to think how many coastal seas, bays, fyords I want or need, as well as useful peninsulas and capes. Of course major rivers eventually end up at sea, so I try to imagine how many I need and where they go, based on other existing geographic features.

On your land-locked region of Besmakia, which you describe as Eastern European like. When I think of Eastern Europe, both the Carpathian Mountains and the Old Forest of Eastern Poland first come to mind, which describes a more greatly wilderness and unexplored region then elsewhere on the continent and that provides me plenty of ideas on developing an area like that.

Regarding trade routes, I try to imagine areas of difficult train and how negotiate them, passes through mountainous regions, long stretches of road across trackless steppe and deserts, how to bypass a primarily hostile region with militant governments, areas with bandits or barbarians.

Make a list of aspects you want to include and decide where to distribute them best in your map. I am sure you have some idea on where one nation is located in relation to others, use that as a guide while developing your list of coastal and geographic specific locations.

I know many people are influenced by real world geography like Eur-Asia and North America. I try not to let that guide me overmuch, and try to stay original in my concept.

Is there anything more specific you want in suggestions to do a better map?

GP

Thanks for the reply GP!
Good advice all, I will try to take it into account the next time I try to draw up the coastline.
I realize I explained something a bit badly (I have now edited it in the original post); Besmakia is probably not landlocked itself, but is directly inspired by Eastern Europe so I'd like to come to some kind of compromise between those two "concepts".
Meanwhile, I have found some real world maps I sort of like contourwise and in that they have some variety betweend the different peninsulas and bays.
 [link=hyperlink url][/link]  
Ancient Persia
Old map of Eastern Europe
Of course, the last map is old and has very soft, smooth coastlines. In the final map I'd like them to be more rugged.

EDIT: Beautiful old map here by the way: http://www.sonofthesouth.net/revolutionary-war/maps/old-world-map.jpg

Trying to "zoom out" to get a better idea of the scale of my world, I drew Itelghast and Ieshyn in a satisfactory way but then couldn't find a way to place Besmakia in between the two.
I'd like Besmakia to be the underdog, the small nations caught between empires, but I don't want them to be a tiny island-continent completely separate from the other continents. Supposedly Besmakia is connected to Ieshyn through the Umbilical, but if I don't connect Itelghast (the most northern landmass) to one of the others then Besmakia again becomes this weird island-continent...
If I connect Itelghast to Besmakia, the inland ocean becomes closed off and the Umbilical would inevitably end up on the wrong side of the continent.
If I connect Itelghast to Ieshyn I end up with one supercontinent and some silly little subcontinent.
Maybe the solution is to make Besmakia larger compared to the two others which have been fairly large until now?
This probably makes no sense without visual aid, but I hope you get something out of it and can help.

EDIT: another solution would be to make more landmasses to even it out. The issue is I'm not sure if I have enough content for that. I guess I can always zoom in on a single part of the world and do that first.