I would however place my POI roughly where they should be in relation to each other (to the north of the city, south, west….)

As for giving the feel of exploration, I think that depends on the number of intersections your party have to come across before reaching the POI. 3 to 4 (including the branching from the main road – blue line) is a good number. 3 intersections gives the party a 25% chance of finding the POI assuming a 50%-50% chance at each intersection (the first intersection is a given… of course your PC will venture into the Forbidden Forest, that’s why they are here)

So how does it play?

I assume the party knows that the Temple of the Lich-King (Major POI) is somewhere south of StartTown (Major POI). That’s how it would read;

DM: As you mount your horses and take the southern road (blue line) toward NextTown (Major POI), you come after a while upon a small trail (green line) that cut perpendicularly to the road. Logs have been carefully piled up to the height of a man (red landmark). The path leads deeper in the forest. What do you do ?

Party: We take the path

DM: The path takes you deeper into the forest until you come across a clearing (red landmark). Woodcutters have obviously been hard at work here (reference to the previous landmark – logs). From you vantage point, you see that the path you are following continues ahead to the North West. You also notice a small hill that overlook the area. There something half way on the slop. The hill is not far but from where you are, it is hard to figure out what it is. It looks like some kind of stone structure. What do you do? Follow the path or go to the hill?

Party:… mmmm… I wonder what is on the hill, it could be a clue. Let’s go for the hill

DM: You quickly venture forward and rapidly lose sight of the clearing. That said, you only have to follow the line of the steepest slope. After a while, you clear the tree line and start the ascension of the small grassy hill. It’s definitely a statue, roughly the size of [insert name of tallest PC]. It must have rolled down from the top of the hill and ended where it is. It’s broken in two, old and eons of rain have nearly washed out any feature. Yet you can make out the outline of what must have represented a warrior clad in antiquated mail armour.
The top of the hill provides a good vantage point. The sun is high in the sky (idea of time) and you can see on the other side of the hill a gentle stream (green line) that snakes at its foot. It must provide an easy route to the heart of the forest. On the left, you also notice that the forest itself seems to grow wilder. A strong pungent smell of rotten leaves waft across the small hill. Large bushes of briar, some big as small houses, have overgrown the forest in that place, creating some kind of thorny labyrinth (green line). What do you do? Follow the stream or explore the briar patch?

Party: …. Welll…

Then depending on their decision/map/mood of the DM they either

a) encounter a major road (blue line) / another intersection
b) the Temple itself

Tabulazero, Thank you for the advice…The lines and the POI actually makes some sense. Does each hex have some sort of distiguishing feature quote: “…a quick landmark description next to it like “river”, “small trail”, “hill overlooking the area”, “glade”… “end quote. Or do we just do away with the hexes all together. I do like the idea of descriptions for each section of the lines.

I make up my POI’s for a general area, like some for a swamp, or for a forest. Then I drop them in when and where I need them. My map is just marked to indicate “something” is in that hex. It’s definitely not “set in stone”….I try to stay very flexable. That way I can use the really great POI’s when they fit the situation.

Part of what I guess I’m trying to figure out is lets say the party knows there is a POI somewhere in the dark forest, the general area, just not the exact location. What’s a technique to simulate them searching the area to find it….

Instead, I recommend that you be a bit more flexible. Unless there is a specific reason for a minor POI to be in a given location, use placeholders instead when you generate your map.

When your party get there, chose from your list of prepared locations what exactly they find there, depending on your mood and the level of the party. Update your map accordingly.

This gives you more flexibility and avoids wasting time coming up with a brilliant location that no one ever come to visit.

What I recommend is as follows:

Take a piece of paper and a black pen. Put your town in the middle. Scatter your POIs around. Take a pen (a blue one). Link your main POIs. The blue lines represent the main roads, they are well known and well travelled.

Take another pen (a green one). Draw a secondary network linking your minor and major POIs. Do not be afraid to intersect the blue lines and the green lines. There are also sometimes different ways of getting to the same POI

Now, for each section of green line, write a quick landmark description next to it like “river”, “small trail”, “hill overlooking the area”, “glade”… You may also want to put a landmark and a description next to where lines intersect such as “The tavern of the weary traveller”, “the old raised stone”, “the gallows”…Write them in red.

When your players travel, read them the map and give them choices:

“As your party travels on the road (blue line) to NextTown (black POI), you come across a river that lazily snakes across the land (green line). Luckily, a rickety wooden bridge (red landmark) spans the length of the river allowing you to continue forward. That said, you notice that a small towpath that runs along. Which direction do you take”

Correction: There are usually a few known locations to start with.

Right now I’m running a 4e game, but I’m more interested in an AD&D type game. It would be sort of a sandbox game. I generally like to map out a smaller area around a starting village/city and put various interesting ruins/lairs/dungeons within that area to be discovered. There is usually a few know locations to start with. Is that a little clearer like mud now…:)

What system?

Emphasize that they’re doing useful work that they’ll see a return on. A “complete” character whose background never affects the game feels like a waste of time. But if I tell you that my village burned when a dragon attacked, and I want revenge…

Generally, if a circumstance means you have to talk to the players that is the best course to take. Be really nice and tell them what they’re missing not what you want. Offer them something new to try. If that is their gaming style you might as well work with it as it won’t change quickly. Keep on offering the carrot but don’t create a situation where they are only motivated for shinies.

In the case of backstory, you can tell them that they are making your job harder and hurting their enjoyment by not giving you material to customize the setting.