Hill Cantons just posted about the tedium of wilderness travel and I was recently struggling with the same thing (you think a hex crawl is boring, try the ocean!). The first default answer to this is to include terrain-based encounters on the wandering monster table. That's fine, but if you don't roll an encounter . . . the default is still nothing happening.
Weather charts try to balance interest with plausibility, so usually you have the kind of weather you'd expect for the season and it doesn't change much.
You could just make something happen each day of travel and prepare a big chart. That's how I handle my abstract city Nidus. Every trip into the city rolls on the table, often these are more exciting things than what the players intended to do in town. But two things, 1) players entering Nidus are playing a mini-game (they have to roll dice to find what they want), so it's more interesting than just something happens guaranteed and 2) a teeming fantasy city should feel different than the trackless wastes. Do we really want something happening every day of travel or every hex travelled in the wilderness?
So how do we avoid the boredom of nothing happening while giving the feeling of travelling through vast, treacherous territories? I think a mini-game is the solution. Almost exactly a year ago today JDJarvis suggested a roll-to-get-out-of-hex-mechanic to spice up wilderness travel. I think he was on the right track. I think it should be a little more involved than that though-- complicated enough that players can make decisions and devise strategies. I also think each kind of terrain should have a different mini-game. The challenges of travelling through the Arctic are different than the challenges of the swamp.
What the games would be I haven't quite figured out yet. Maybe you could help. But here is a proof of concept I whipped up for swamps:
I think the biggest ongoing threat from wetlands is . . . well, the wet. The damp gets into food, ruins boots, and wears down pack animals trudging through soft, sticky earth. So you might make every day in the swamp (travelling or not) give 1+ 1d4 squares of dampness damage.
Players can choose where to put this dampness damage: on boots and armor or on pack animals. The idea is you can privilege your gear, keeping it dry by overloading your animals or save the animals by trudging through the wet muck yourself. When the dampness bar is full, the animals are through. They are lame. They've been left in sinkholes. For the boots/armor I'm not sure. You could say all armor becomes worthless, but that's pretty harsh. Maybe start taking dampness damage off of AC, once the bar is full, one a day. Loss of boots should mean slower movement rate too.
You can reset the bar by finding a dry enough spot to camp-- one square cleared per day of fire and rest in camp (props to Wilderness Survival for that idea).
The squares on bottom are if you have a one of any of the labelled folks in the party. You can sink one square of dampness damage per day into them. The idea is that through know-how and experience they help the party avoid some of the most difficult terrain.
So what choices would this give a party? Well, in an emergency they could work the animals so hard they sacrifice them, but then you would need to be strict about encumbrance to make that matter. Or if they are going to need their animals on the other side of the swamp they could store all their armor, sacrifice their boots and travel very slowly. But if nothing else I'm hoping there would be tension as they split dampness between both bars and looked for a decent camping spot. You could even set a minimum elevation ahead of time and use this technique as a sub-mini-game.
What do you think? Can you invent entirely different games for desert/tundra/ocean that would be interesting and "feel" like those places?