Ever since I was a kid, I've been really interested in making maps for my worlds. Tile map systems like RPGmaker facilitate that kind of thing with a speed that's really hard to explain until you try it yourself from scratch (which I have - and let me tell you, it's a nightmare).
What I modeled my map goals on are not going to be the same as what you might want for your world, but it might be inspirational to someone else out there wondering what kind of work load this really takes and how to simplify the process.
numerically, I based a lot of my map dimensions on Final Fantasy series, particularly 2/4. It seemed the most manageable project scope and still vast enough to keep me occupied. It also makes use of alternative world maps which gave me all kinds of ideas.
World Map
first you have your world map. Its some kind of low resolution super deformed chibi map with very generic icons, such as mountains, grass, forest, swamp, fresh water, sea water, cave entrances, towns, castles, and darkness, such as a hole in the world. This is sometimes known as your airship map, and is basically a very large map with a very simple tileset, and town and cave event icons transporting your deformed sprite (2 heads tall usually) from the world map to the town/cave/etc. map. You can also trigger random combat here.
On a large world map you want a nice number of event locations. I recommend 17 as a good starting number, but a few less or many more won't hurt. I would recommend avoiding having less that 13 event locations. You can also have a few other world maps for an under world, outer space, under the sea, on the moon, in the afterlife, after the world has been destroyed, or whatever suits your fancy.
You can even create clip scenes between transports to give the effect of flying from one to the next.
Areas
Next you have what I call areas. Areas are collections of maps tied together by transport boarders and things like staircases or entrances, where your sprite generally stays the same and you don't go to the world map to get to the next area. For example, caves, cities, towns, castles, and so on. You want about 17 or more of these areas, connected by world map events, generally speaking, though you can also link maps using special events like a teleportation chamber.
Rooms/maps
Further down in scale you have Rooms, or as the computer calls them, maps. I've counted, and it appears that most areas have an average of between 9 and 20 rooms, those things that have their own tile sets and are called "map00x" in the computer.
Here's the basic math to it all:
if you have 9-20 rooms per area, let's call it 16 for good measure,
and you have 13-29 areas on your world map, we'll say 17 for a nice low average,
then you need about 200-300 little rooms, in bundles all across your world map. One of the ways to cope with this is planning some areas as being "larger". If your standard room is 15x20 tiles,
then a 30x40 tilemap is actually 4 rooms, while something like 60x60 is 12 rooms. You can place these center piece "islands" in your areas and then attach smaller rooms all around, or you can work the reverse and make a tatami map pattern, with a small map in the center and boundaries connecting to each other, for an average of at least 9 rooms.
I also recommend using a lot of terrain features to keep people from using too much boarder space when traveling from room to room. In some places, you will want things wide open, but in general, making 50-70 events just for transport purposes, PER room, is going to end up being over 10,000 events dedicated to transport. That seems like a waste to me.
Well, I hope someone finds this useful or interesting ^^