First attempt hand-drawn Regional Map, need help

[Knighthood]

Hey All,

A while back I drew a horrible outline of a country/continent I was doodling, after looking at it and doodling other things I realized I was crazy (still am??) and it didn't make sense, especially after a fellow cartographer gave me some advice on planning.

So I have a new area I drew, and I moved down to a regional level, and I need assistance with scaling and reasoning. I'm trying to create a landmass, kind of peninsula in essence, that has a high sea wall and a small bay area in the South East. The main connection back to the mainland is surrounded by mountain ranges to the North and West, giving access through a gap between the two in the North Western part (where, I drew a rudimentary wall).

I know this idea is moving forward, but I feel like there are so many wrong things artistically (and sorry for the faded images, this paper doesn't hold graphite very well it seems) and geographically, but I'm mainly wanting to focus on the geography issues. Overall, the question is, does this make sense? Is this possible? To give more of a description of what I was thinking for this area: There would be 5 cities; a large trade city on the coast where the river runs into the bay on the South Eastern part of the map, the main capital city where the two rivers from the mountains to the North and West meet, two dwarven cities in the mountains where those same rivers start (so one mine in the Northern range and one in the Western Range), and then a city built at the bottom of the massive wall that bridges the two mountain ranges in the North West.


Any advice and assistance will be greatly appreciated, and thank you very much!