I will start a new game in my homebrew setting soon, and being a prehistoric world that is mostly wilderness with just some small villages clustered in a few areas, PCs will regularly be spending a lot of time in the wilds and off the few roads there are. Even if it's just patrolling for monsters or bandits near their village or making a quick visit in the next village on the other side of the forest, every adventure that does not take place in just a single village will have wilderness passages.
In the past, I almost always skipped over those parts. Because traveling on a well known road during spring or fall, what could really happen that wouldn't turn into grinding routine after the third time?
But for this campaign, I want to make it a major aspect of the game, and so I want it to be something exciting and not dreadfully boring. Since I barely ever tried it, I am needings lots of help and advice on this.
I think I will be using the hex-maps from Ultimate Campaign. Without modern maps based on extensive land surveys, any location that isn't directly next to a landmark that can be seen clearly from a dozen miles away or along a road will be hard to pinpoint exactly even with a map. If the location of a destination is narrowed down to a single hex, the exploration rules can be used as a base to determine how long it takes the PCs to find the exact place they are looking for.
Also, it's easy to track where the PCs actually end up when they are getting seriously lost.
Some things I am completely lost about is keeping track of supplies. Should finding food and water be something that is relevant unless the characters are traveling though deserts or mountains? I expect almost any character to have decent ranks in survival and simply moving at half-speed for a day to restock supplies seems a bit boring and not interesting at all.
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I've played in a 3.5 game that takes place in a swamp, around a small village. We were a cleric, fighter, and rouge. None of us had survival so we had to stock up on supplies and hire a NPC guide everytime we left the village to avoid getting lost. The NPC was with us for so many random encounters that she ended up leveling and taking a ranger level.
Things to keep in mind for wilderness travel.
1) Food and Water. (DC 10 to feed yourself for a day, not to hard but slows you down so if your on a timeline it could cause some problems, also you could require K. Nature or a second Survival check to avoid dangerous food and water sources)
2) Getting Lost (Survival again, the interesting thing to note here is Poor Visability. Way back in the movement section of the book states on a table that Poor Visibility doubles movement costs. So you end up spending a lot more time in the wild.)
3) Enviornment. (Lots of neat little rules that often get overlooked such as the Stealth and Detection Rule which is where you get the poor visibility distance.)
4) Disease. (Not exactly fun on it's own but creaturs can spread Diseases with Natural Attacks so if you have a beast with clear signs of a Disease it can make your PC's rethink how they handle the encounter)
5) Population. (You will want to create your random encounter charts, I suggest you stay small. A few Animals, Insects, Magical Beasts, Indigenous people [For my swamp game it was cannibal elves], etc. Have a chart for level 1-2, 3-4, 5-6, etc. Keeping the list small gives the PC a feel for what lives in the area, with new things appearing slowly as they level or as a non-random encounter.)