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My players are going from Neverwinter to Comyr in D&D 4e Forgotten Realms.

So, what I do everytime they travel is, learned from The Order of the Stick, a single random encounter (which, honestly, is bothering me) and a detailed description of how the world looks different geographically speaking. I have to say this is something I've read around here before and I liked it. Though some things that ARE supposed to be random are missing. Honestly, I use the road time to add some important things to the plot sometimes and even divide the long travel into some smaller adventures. But I still feel like there's something missing every single time. Something that makes the players actually feel like they've spent that much time between cities. Listing:

  • Even though there's some roleplay during travel time, what about really long distances? My players are about to spend 31 days on the road and the last time it happened I didn't feel at all like they spent all that time together. How do I make them feel like they had to put up with perks and quirks of their comrades?
  • What about how to make the weather and landscape a challenge without making it just a "skill challenge" or, in other words, a "dice roll" matter.
  • How to make a random encounter between long distances have the same mystery and feeling of a locked room in a dungeon? It's easy for the players and I to build the needed atmosphere when they are exploring the lost temple of a forgotten god and they already know they might expect weird things behind each door but it doesn't feel the same for "And when you arrive in the Trollbark Forest, you hear weird noises from behind the large trees". They always say things like: "Time for the random encounter, guys".
  • How do I make random encounters more of a risk to be avoided than a chance to get some XP? 1 random encounter per travel is the standard way of not getting the group bored but it's called a random encounter for a reason. Travelling in a Medieval Fantasy World is supposed to be dangerous. Also, there must be a chance of them to randomly face a creature way more powerful than they are but reducing it to dice rolls seems to destroy the feeling of travel. Is there a known way of making it possible for the players to have more than one encounter in a way it doesn't feel like: "Oops, I rolled two 6s" or "Unfortunately, the ranger failed his check to guide you guys safely"?
  • This is a tricky one. How to make the encounters actually feel random when you're supposed to make them face monsters that are a challenge but won't be too easy (otherwise it won't be fun and will only take time) or too hard always (then it becomes a constant thing for them and also, makes the world to feel unreal since they'd always face challenges up to their power, no matter where they go to).

I know this is a quite hard and complicated matter. I'm an experienced GM but there's also room for improvement. I feel like I do things quite well but there's always something to learn. I don't expect a magical solution but it would be great to have something that'd solve at least part of the problem.

In the end, I just would like to add that even though this question is about my D&D 4e group, this is pretty much a system-agnostic question. So I'll be accepting answers that are system agnostic but I also will accept any sort of mechanical solution if it solves my problems when GMing with this system.

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I see two primary ways to approach this, depending on the travel. (TL;DR at the end)

Travelling through civilized lands

From your description, it seems like your players (who are, considering you are playing D&D4e, are basically powerful heroes) are travelling between two cities in a civilized nation. In this case, I'm not even sure if I'd run any kind of straight forward combat encounter. After all; it's not much of a civilized country if random merchants have a high chance of bumping into something that's a threat even to a group of adventurers. They would be scared to travel that road, and with good reason.

Instead; make a list of random encounters that highlight the kind of things you would expect to see on such a road. These can be short (like a few minutes), focused on roleplaying, and highlight exactly the things that make this part of the world unique. They can be dangerous situations, but they should be dangerous for others and mostly resolved by talk. They can also simply be amusing, peculiar, atmosphere building, or setting up for later adventure.

Each should have one or more actors and a situation that is happening. (Those without actors other than the players are usually boring; those with actors but no situation are usually just ignored)

I don't know the setting you're using, but I'll try to make a list of the kinds of things you can run:

Generic Actor examples:

  • A single traveling merchant with a backpack. Would most likely be a bit scared of meeting what looks like a warparty.
  • A traveling caravan. Will have their own guards, might even sell the players some stuff. Probably cares something that is of no interest to them, like food, cloth, ore, etc.
  • A noble party. Might be out hunting, might be on a diplomatic visit, might just be taking a stroll. Will have lots of money and gear, guards, servants, etc. Would probably be a little disdainful of the players.
  • Hunters or farmers. Probably just out working, mostly disinterested. Or maybe just slacking off and caught in the act.
  • A military patrol. These guys are the primary reason you don't get random encounters that involve very dangerous creatures. Will ask some questions about why an unafilliated group of heavily armed people are traveling the road, probably.
  • Some form of wildlife. Could be a wolf, or a deer, or a group of rabbits. Will probably just be scared of the players and run away (yes, the wolf also)
  • Bandits. Will probably not ambush the players because they are not suicidal, but might be seen in the bushes, or pop up only to realise their mistake and start running.
  • A fellow wandering adventurer type. Might be a good one, might not be. Might just be a travelling bard or a local druid.

Next, come up with a suitable situation for them to be in. Maybe two of these groups have bumped into each other. Perhaps the nobles ran over one of the farmers, and now he's wounded. Maybe the military patrol is questioning and intimidating the lone merchant. Maybe a travelling cleric is annoying a hunting party. Maybe the bandits are ambushing someone just as the players approach.

Let them roleplay through a few of these simple situations, interspersed with "for a few days, nothing interesting happens.". This will give them an idea that things happen in your world; you get some chances to tell of the changing terrain (seeing more and more military patrols in these little encounters would reinforce the idea of heading into a dangerous or militant country, while meeting more travelling bards would give a very different kind of country)

(If you run something along the lines of "you find bandits ambushing a farmer", don't grab the dice. Run it more like either the players scaring off the bandits and the farmer thanking them, or a hostage situation. These bandits are no match for the players and they know it)

In addition; if you want to highlight the strain of long time travel with a bunch of quirky people (like most adventurers are), ask each of them beforehand to give you one description of something his character does during the trip (or does in general) and then for every long travel randomly pick one of these things and use them as a highlight in the travel.

If your party Elf has told you that he likes to sing during the journey, run one short encounter that starts with "Today has been calm. For the 10th day in a row, the Elf has spent most of the past 6 hours singing.", followed by a bit of silence. If the players care about interparty social interaction, they'll probably jump on that cue and have a few interactions. (If they don't care, they won't but you probably can't make them anyway)

The more of these short moments you have, the longer the trip feels. If the players are preparing for a long trip then you shouldn't feel bad spending an hour (or two) just doing a bunch of these. I've spent half of my last session mostly like this; just the players bumping into various characters from the region they were in.

If your players start getting bored, you can consider throwing in something with a little more threat but an easy option out, so the players can decide whether they want to pursue or not. Instead of having a Hydra come crashing onto the path, have someone bump into them and warn them that he's seen a Hydra in a nearby cave and that he's scared it'll attack a nearby village. It shows them the world can be dangerous, without being continuously attacked by things, and gives them the option to roleplay saying "no".

Travelling as an adventure

When a travel is through more of a wilderness area and for long duration, you should treat the voyage like an adventure in itself. Map out some things that are going to happen on the road (these don't even have to be random) and then see what the players do.

Make sure you spend some time at the start where the players prepare for their journey. Let them get some information about likely things to encounter (in terms of terrain, weather, villages, monsters, dungeons, etc) and give them time to prepare for these things. As they start on their journey, use short roleplaying encounters as described above as they set off, but alternate them more and more with encounters with more dangerous and uncivilized opponents. Their journey does not start in the wilderness most likely; so as they set out they will meet some merchants and workers, then at some point mostly military partols and some workes, then military patrols and the occasional savages/monsters, then at some point only wilderness encounters.

All of the wilderness encounters should still have a situation that doesn't immediately involve combat. Running into a party of Goblins that try to kill the players is a cliché, but running into a party of Goblins that are picking berries can also be very interesting (and quickly turn into the former if the players approach it wrong!)

When it comes to the players maybe facing something much more powerful, that's also a case of foreshadowing. The odds of two entities traveling a land to randomly run into each other is very small. However, if one of these two entities is trying to find the other, the chance goes up considerably. But that also means you might get early warnings. This is then the best way to set up the atmosphere for a "random" encounter.

Consider the following series of encounters:

  • A group of Goblins hiding under a large plant. Some are scavenging mushrooms while others keep watch. They seem to have their eyes mostly on the sky. If the players try to talk, they get "shush"ed. If they try to speak softly and in Goblin, they get warned that there might be a Dragon in the area.
  • The players see smoke up ahead. They come upon a clearing in the forest. All the trees in a 100ft area are smoldering, some plants and trees are still on fire.
  • A massive shadow flies overhead. Looking up, the players see a huge creature going off into the distance, but it does not pay them any attention.
  • The players come out to a slope down; no trees grow here and the path down looks treacherous. As they struggle their way down, somewhere ahead in the forest, not that far away, they see another pillar of black smoke coming up. (This will probably make them go "uh oh", but nothing else happens)
  • The players come upon a small plain in the middle of the woods. Nothing to give them cover; but no real way around it. As they step out into the clearing, the Dragon they've heard of, seen overhead, and whose path of destruction they've witnessed slams down behind them and lets out a terrifying "FOUND YOU!" before opening its mouth.

The above is, ultimately, the same as just pitting the player against a Dragon in a featureless plane, except that now the atmosphere is set, the players get ample opportunity to come up with plans to avoid this Dragon, it doesn't feel random, the players will probably not go "oh a clearing, time for some random encounter" (even if they know exactly what is going to happen) and it'll feel like they've been travelling for quite a while.

Likewise, you can use weather effects without dice rolls if you make them a part of the story. Rather than saying "it rains, roll Endurance", you can simply make the observation "dark clouds gather overhead. you remember the warning the villagers gave you about how rain can keep coming for days on end." and go from there. If they decide to travel through it; tell them how they get chilled to the bone. Ask them how they'll deal with that. Only use dice when they keep ploughing on without taking any precautions. (And make those dice hurt)

Giving them foreshadowing, the option to adapt their plan, and letting them avoid much of the nastiness if they came prepared makes the world come alive. Having 3 short encounters where the rainfall is described as "continuous" makes it feel like the rain is really, really bad. Players will learn to measure travel by how many small things happen on the road, and anything that keeps happening during all of them will also start feeling really long.

Extended example from my last session

Setting

This took place as my players prepared to venture from their old city towards an ancient, abandoned temple to the dragon god of culture in the hopes of fixing their dead friend. They knew very little of the place other than that it was abandoned and lay deep inside Kobold territory.

Prep

At this point the players had the option of making their own plan. Main part of the plan was the party Druid going to have a chat with the Kobold Druid who was a member of his circle and responsible for the Kobold kingdom. This meant a roleplaying encounter where the Druid first talked with the Kobold ingame. They learned that they needed papers to travel safely.

After this, the players took some time to gather their stuff, bought some travel gear, and set off.

First encounter

Shortly after entering the Kobold lands, the players encountered the Kobolds; one of their Sorcerors and his bodyguard blocked the path and interrogated them. Remembering what the Druid told them, they asked for travel papers. After some haggling the Kobold sold and prepared their travel paper. He also explained the rules (no digging, no cave exploring, no entering Kobold settlement)

Second encounter

After shooting a deer, setting up camp and having dinner, the players go to rest. The following morning, the remains of the deer have all gone missing. The guards hadn't noticed a thing until it was gone, but scouting in the morning finds various tracks of Kobolds around their campsite.

Third encounter

Travelling further, the players come near a Kobold village. Again they run into bodyguards, who ask them about what they are doing near the village. After a show of papers the guards send them back around the village and they continue on their way.

Fourth encounter

In the woods ahead, the players come across the corpse of an Ogre. It seems to have been killed by small stabbing weapons. Doing some research around the site, the players learn that there's more Ogres that left the scene, but no sign of any struggle or marks of other creatures. A little worried, they push further.

Fifth encounter

From up ahead, the sound of giant feet can be heard. Ahead of the party, two Ogres burst from the path, in obvious panic. In an attempt to regain their composure and hide their fear, they act tough and threatening to the party, which takes no time to answer equally tough and a short fight breaks out. (The Ogres are not much of a challenge)

The players wonder amongst each other what scared these Ogres so much, and remembers the other corpse they found. More worried, they push on.

Sixth encounter

The morning after battling the Ogres, as the players break up camp, they encounter a necklace made from Ogre teeth hanging near their tents. No tracks of any creature can be found, and the night guard hadn't noticed a thing. The players decide to put up an extra watch from now on.

Seventh encounter

After a few days of finding little but the occasional Kobold guard near a village (at this point they've seen enough of them that it becomes mundane, and they are mostly just a quick reference unless they have something important to say) the players start coming closer to their goal. During the day, they notice a hawk that seems to follow them around. In the evening, as they make camp, the hawk sets down nearby to watch them. The party Fighter, being ever the pragmatist, decides to shoot it. The following morning as they wake up, the Ogre-tooth necklace has been stolen, although the Fighter was wearing it as they slept. The night guard, again, saw nothing. The players are now extremely worried, but realise they can only push further.

Eight encounter

The players spot an abandoned castle on a hilltop. Curious about whether this is their destination, they decide to ask the nearest Kobolds about it. The Kobolds tell them the place is haunted and they never go there, but it's not the temple they are looking for.

The word "haunted" seems to draw the party's attention, and they decide to check it out in hopes of finding treasure.

Ninth encounter

The players check out the castle, which indeed turns out haunted. As they walk around, various mysterious things happen (fires suddenly going on, wind blowing inside buildings, rumbling sounds). As the players are eager and continue to explore, I realise they are probably looking for something exciting, so I fill in the haunt by having Elementals appear from the castle, which engage them. The players realise they've bitten off a bit more than they can chew when after the first wave, a second, much larger Elemental starts to form nearby, and quickly leave. (I make a quick note that they might want to come back here later)

Tenth encounter

The players push further out, until they see in the distance two openings in the woods, fairly close together. At their next chance they again ask one of the Kobold guards whether this is their target. The Kobold explains that one of the two is a large Kobold city, which is off limits, and the other is their goal. He also tells them the Kobolds never go near the temple, or the city it's in, but that it's all on them what they do.

Arrival

The players arrive at their destination after a long, dangerous journey through Kobold lands. They are still full of questions about the Kobold empire and the strange things that happened to them, but they set it aside. As they travel inside the city, many more exciting things happen, but their travel is over. It took about 4 hours ingame time if I remember right, and certainly felt like an adventure. And of course, there´ll be a trip back if they make it through the temple. During that return trip, at the very least they´ll run into the mysterious Kobold Giant Hunters they heard all these rumors about...

Summing up

TL;DR:

  • most encounters shouldn't revolve around something killing the players, especially not routine travel in civilized lands. Creatures are generally not suicidal and have their own lives. Goblins also need food, they also farm, mine, build, trade, etc.
  • the more minor things you let happen on a travel, the longer it feels. 6 very short (5min or so) roleplaying encounters with a "you travel 3 more days and then.." feels much more like an actual travel then "you travel for 3 weeks".
  • using minor non-combat encounters can help you show how the landscape and country changes, as you'll have time for it without making it super obvious.
  • don't just drop random encounters on players; foreshadow them with said minor encounters. Fighting a monster is much more interesting if you've seen what it's done with the local area first.
  • things don't randomly bump into each other. Usually one side goes actively looking for the other; use this to make the story more interesting.
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    \$\begingroup\$ What an excellent explanation of what sounds like a great method for building the world and keeping interest going. I'm going to definitely adopt some of this next time I get the chance. \$\endgroup\$ – Matthew Walton Jan 15 '15 at 15:43
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    \$\begingroup\$ This is a wonderful guide for overland journeys! I'll be sure to refer to it in the future. Well done! \$\endgroup\$ – HighlandRat Jan 15 '15 at 20:31
  • \$\begingroup\$ I never actually just roll and say "it's raining" but I like the feeling that some things are random. As in rain or encounters, but I wanted to make it in a way that it would feel random without making it feel like a dice roll if you understand me. Anyways, this is a great guide. It cover pretty much almost everything I needed. And I can certainly use this and add a few things here and there that I know to work on my players. Thank you so much. \$\endgroup\$ – Davi Braid Jan 15 '15 at 23:59
  • \$\begingroup\$ @DaviBraid if you want to make the weather/etc random, you could always make yourself some "random weather tables"... check out the description and example here: pastebin.com/4BuzSabT \$\endgroup\$ – Doktor J Jan 16 '15 at 19:48
  • \$\begingroup\$ I have played and GMed tabletop games for 6-7 years and I learned a lot from this answer. A well-earned +1 for you good sir, and your advice will be taken without shame by myself. \$\endgroup\$ – Lucas Leblanc Jan 16 '15 at 22:05
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TL;DR: Skip random encounters, make encounters during travel meaningful for the story.

Travel, as any other part of game you play out, should have a purpose. Actually, it should have several purposes: Involve the players, let the characters shine, move the story forward, add to the world.

If all you'd do with traveling is get to a new place where the interesting and purposeful encounters happen, do a cut-scene and continue where things are interesting.

If you want to play out travel, you should closely tie it into the world:

  • Use travel to provide background information: Players are entering a kingdom where slavery is allowed? Have them wonder about the long lines of people waiting to leave that kingdom, because the guards have to inspect each and every cart, and each and every person, to ensure no slaves escape. Next, confront them with an escaping or mistreated slave - will they offer help and fight the authorities? Finally, have the bard be mistaken for a slave when they stay at the inn. By the time the players arrive at their destination, they know the local culture, they have taken a stance on it, and they may have pissed of people who will try to get back at them.
  • Use travel to tie up loose ends: Maybe there was a merchant who supported the bad guy, and was able to get away? Have the characters notice a wrecked wagon on the side of the road. Once they get rid of the wolves, the characters find what remains of the merchant and his every-annoying grandmother, but notice that the merchant was executed before the wolves came, in the bad guy's characteristic manner. Or maybe they find the wagon guarded by some lizardfolk. The lizardfolk are just scavengers, but they will defend their loot - what could the ranger offer them to get his bow back that was stolen by the merchant?
  • Use travel to foreshadow: Say the characters travel east-west. On their way, they meet an army traveling north-south. War is coming to the region, their destination may already be in ruins. Will they make it before the library burns down with the rest of the city? In one game, I had the characters travel along a road cutting through a supposedly haunted forest. At each entrance to the forest, there was an inn where you could hire rangers to guide you through. After some complications at the inn, the characters ended up entering the forest without a guide, and they just barely escaped with their lives when they were attacked by ever stronger waves of giant spiders. Imagine their dismay upon learning that the big bad evil guy had set up his lair in just that forest.
  • Reveal delayed consequences of the player's actions: For example, the characters may be warmly greeted by the family of one of the children they saved from the big fire (and learn that there are some annoying goblins nearby). Or they may be confronted with a skill challenge when the strap of the saddlebag that has miraculously saved them last fight breaks just as they go over a slippery bridge. Or they may learn that the price of ale has gone up in all the inns, rendering the patrons belligerent, because some goody-two-shoes have shut down the brewery that illegally used gnomes as slaves.
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Another idea that can sometimes apply, but perhaps not in this case, is to set up a tight deadline.

If your party has only 16 days to get from Alpha to Beta before something happens (obviously not "you lose" but rather "things get more interesting"), then you could show them on the map that the safe route from city to city along patrolled roads takes 20. One of the patrons of the tavern insists that there's a faster route through these woods, across these plains here, and along a secret mountain pass. That should only take 12.

Then, you have justification for why some of the monsters are stronger than the random peasantry that likely travels in this area.

You could also be setting up an intrigue. Perhaps there's a camp of bandits waiting just inside the woods to be fed travellers such as yourselves by that guy in the tavern. That could be combat, or it could just delay them a day or two. Now they might not make it in time.

What it also allows is for weather or other things to have a more tense effect. Because players are on the clock, on one day you could describe seeing a bunch of dark clouds ahead of them across the plains. They march on, because that's what they do.

The next day, though, it's raining and altogether pretty miserable, but they manage to push through without losing too much time. The next day they keep going, but the storm is getting really bad, and there are very real consequences to continuing. They are essentially fighting the storm. They may decide to push on, or they may decide to take shelter.

The next day the storm seems as bad as the day before. At this point they could be looking at their map, and getting really nervous because it's been 10 days so far, and they've been holed up for 2, which only leaves 4 more to get to the city on time. The next day, maybe, the storm seems to have let up enough for them to continue.

Maybe a day or two later they can just see the city on the horizon, when suddenly a family jumps onto the road and asks for help. Their village is being burned down by bandits, just over that other hill. Obviously the bandits would be no match for your party, and obviously they'd love to help, but they're not fighting bandits, they're fighting time.

They can see the city, but figure it'd be another day and a half travel, and that's cutting it close already. How much time will the bandits take?

Maybe the bandits take off when the party arrives and starts laying down some damage, but with some of the villagers belongings. The party certainly doesn't have time to chase them down, do they?

Along with this, you could also allow them to push through a day, and gain more ground, but at the cost of something. Maybe they're really tired that night from the cold, and their clothes are all wet and soaking into their souls. They just get to sleep that night, when it's interrupted by marauders. Normally they'd be no match, but given the tiredness, and all of your gear's still wet, and the late night, maybe the party isn't as strong as normal, or hasn't yet recovered from the push the day before.

Maybe, after the fight, they aren't even fully recovered by the next morning and have to choose to take it easy, even though they can feel the time slipping away.

Obviously you can't do this every time, sometimes travel is easy, but it can at least be an interesting thing to mix in from time to time.

TL;DR

It can be really hard to feel like the travel doesn't take any time, when you're constantly tracking it, running out, and stressed about its passage.

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  • \$\begingroup\$ I should also clarify that the rain storm I describe is very dependent on setting. It could easily be replaced with a blizzard, avalanche, sand storm, flooding, high winds, etc. Anything that poses some sort of opposition to the party and slows them down. It doesn't have to outright defeat them to be a problem, when there's a clock. \$\endgroup\$ – psycotica0 Jan 16 '15 at 13:49
  • \$\begingroup\$ Please edit clarifications into your answer. \$\endgroup\$ – mxyzplk says reinstate Monica Jan 16 '15 at 15:33
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There's a couple of dials you can turn that create different experiences for travel.

"Are we sick of each other yet?"

First, it's worth noting whether this is something your group even wants in their game at all. Most of us like to play action-adventure RPGs and don't particularly care to endure mundane drama as part of our escapism. Talk to your group and find out if that's even something they want.

Assuming they do, it can be useful to simply give people conditions and XP for roleplaying those conditions: "You're tired and pissed off. Get 25 xp for being snappy."

If you want to see a game that does both travel and group tensions in a great way - Mouse Guard is basically designed to JUST THIS. Getting from point A to point B is a pain in the ass, gives you conditions like "Angry", and then you also get the equivalent of hero/action points by playing out your Traits in ways that makes the trip harder.

Encounters are more than fights

If you always make a random encounter a fight, the players always know they can expect a fight on each trip. If random encounters can be more than that, then you can have a more varied set of responses:

  • A merchant whose cart wheel is broken, and they need it fixed. (will offer supplies in exchange)

  • A priest who is travelling. Sitting down, having a nice meal and chat earns their favor, and next time they go to a nearby city, they find out he's basically the equivalent of a Bishop and he offers them support.

  • A couple of adolescents running away from home. They need help to actually get to civilization.

  • A griffon with a broken wing, and two broken legs. Do you keep away because it's angry and dangerous? Do you heal it? Do you put it out of it's misery?

Beyond just non-fights - give XP for avoiding danger and roleplaying/helping others.

You can also include environmental hassles -a flooded river, a bridge that is out, a mudslide that covers a path. How the characters navigate around these things can be interesting if your players enjoy logistical puzzles.

Consequences and Costs

The first thing is supplies. Food, water, tents, cloths to stay dry and warm. Some of these are consumables and you can track them running down over time - the more time wasted, the more these run out. If a monster attacks and wreaks your pack, how much of your supplies are still with you? ("Ok, we got a problem. I've lost half my magical components.").

This can either be life-critical problems, like in real life, where lacking adequate supplies or tools could have you freeze to death on a cold, wet night, or it can be more action-adventure problems, where you simply rack up a penalty for being sick and cold and feeling crappy. If you're going with the former, you absolutely need to let the players know because it's a very different game at that point.

Having a outdoors-type characters who can find shelter, food and water will be really useful, and having magic to create such things will also be key.

Naturally, supplies also cost money.

Second, time. The time lost to travel, to encounters, to healing up from encounters, to getting more supplies foraging because the giant serpent knocked your pack mule over the cliff... Time becomes important if you've got a deadline.

But it's also important for another reason - everything is based in seasons. Do you want to catch a boat across the ocean? You need to get there before the monsoons hit. Do you want to link up with a caravan to get across the desert? You've got a month before the last one leaves, and then it's another 5 months before trade starts up again. Did you want to buy the Scarlet Herbs of Vizzony? They sell out halfway through the season, and the price increases every week. Both supplies and inn prices might fluctuate based on pilgrimages, holidays and trade seasons.

In most RPGs, characters heal quickly and easily - but it's the pain in the ass of dealing with lost supplies and time that will keep stinging on a trip.

Goal-based XP

A mechanical shift, but a useful one. Only reward actions that go along with the goals of the group. When travelling from point A to point B, the point is to get there safely, not "fight a group of bandits", "deal with weird swamp zombies" etc. So they get XP for avoiding and minimizing a fight, they get less or no XP for engaging with it. Let them know this up front - "Getting into fights on this trip will get you no XP, avoiding them and finding ways to get there quicker, will get you XP."

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What about turning travel time into a puzzle or a "game-within-a-game" to add a little danger and fun to the journey? The hallmark of a fun game is problem solving and having to make difficult decisions.

Without refering to specific landmarks that lie between Neverwinter and Cormyr (I don't have a map of Faerun handy), here are a few examples:

  • Min/max puzzle: Give the players several options for the route they travel to Cormyr. There could be the safe but slow path overland (= more expensive since PCs have to buy more provisions), or the risky but fast path along the bandit-plagued road. Perhaps a gynosphinx known for her merciless riddles likes to hang out along the fast route...
  • Optimization problem: Hint to the players that large parties traveling overland often attract more attention from roving bands of bandits, Orcs, and other nasties (i.e., random encounters are more likely). Smaller parties can often slip unseen through the wilderness while traveling through regions patrolled by bandits. On the other hand, if a party does have a random combat encounter, the more PCs & NPCs in the party, the better the outcome. Make it a math problem! Give the players a few data points and let them figure out optimal party size. For example, splitting the party into two groups while traveling to Cormyr may be the best solution to avoid random encounters. Or the players may decide to beef up their party with hired swords to better survive the trip.
  • Minefield: Make the route from Neverwinter to Cormyr a minefield of monsters and hazards which the players must avoid by finding the optimal route. The nearer the party ventures to one or more sleeping dragons in their dens (especially when upwind), the more likely the dragons will awaken and attack the trespassers. Another option: players have to slip past concentric circles of hobgoblin patrols marching around their home base, whose predictable paths and timetables have been mapped out by prior adventurers.
  • Valley of Death: Instead of relatively static obstacles, create a region along the route, say a steep-walled valley, which is inhabited by multitudes of masterless zombie hordes shambling along random trajectories. The zombie packs "bounce" off each other and the valley walls in a vast Brownian motion simulation. The players must navigate a safe hex crawl path through the valley avoiding the DM-guided zombie hordes.

Just make sure the puzzles don't have trivial solutions. And award clever solutions with plenty of XPs!

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Erik and Jonas had good answers. One more point:

  • Allow the players to describe a camp routine for their characters, so the GM doesn't have to ask questions like "did you post any guards" when it really matters. Let them come up with sustainable watch rotations, or deal with the consequences. Ask them just how much food and water they're carrying, if you worry about details like that in your game.
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    \$\begingroup\$ I think it would have been better for you to comment on their answers rather than add this as a new answer. \$\endgroup\$ – Javelin Jan 15 '15 at 19:09
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    \$\begingroup\$ Could you explain more about how allowing players to describe a camp routine and asking how much food and water they have makes travel more interesting? \$\endgroup\$ – SevenSidedDie Jan 15 '15 at 19:50
  • \$\begingroup\$ @SevenSidedDie, my proposal would make the detailed playing of the first couple of days and nights meaningful. Unless the entire trip is a red herring, the players will think that nothing important happens early on. With the assumption that the players are describing their routine, you don't "waste" playing time on travel. \$\endgroup\$ – o.m. Jan 16 '15 at 6:50
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    \$\begingroup\$ @SevenSidedDie - There are situations where supply logistics could be relevant. For example, if the party is traveling from a city through a desert to their destination, and will then retrace their path to the city after looting the tomb. All water and food will have to be transported either on the adventurer's backs or on beasts of burden (which also must eat and drink). Water is heavy - there may not be enough spare weight for treasure found in the tomb. One solution is to purchase camels. Or instead, go with cheaper mules and bury caches of food & water along the route for the return trip. \$\endgroup\$ – RobertF Jan 16 '15 at 14:21
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    \$\begingroup\$ @RobertF I'm all about the logistics. The question is about how to make travel more interesting though, and the answer is missing any explanation about how this solves that problem. \$\endgroup\$ – SevenSidedDie Jan 16 '15 at 15:09

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