Sooner or later, players need to cross some area to get to somewhere else. Whether it's moving from one city to another, or even one dimension to another, it's a process and there are many ways to handle it. Do we just skim past it and go to the action after? Do we give side content (some levity and variety could be welcome)? If we do, is it a distraction or does it give them resources they need later? Do we do meaningful stuff that somehow ties back into everything? There are many ways to handle such a situation and what makes things even harder is that it can be very situationally dependent. For these reasons I wish to explore the topic a little.
It's Not Easy
Traveling between locations is difficult in tabletop role-playing games. You want to make it interesting as a Dungeon Master, but it's easy to get mired in side details that people don't enjoy. At the same time, you'll find yourself needing to do something involving it if you have a ranger. Otherwise they'll feel a bit ripped off. Part of this is choosing the right granularity. If there's only one choice to be made for a 3 week journey, you might not want to do a day-by-day (asking everyone on every day what they wish to do) unless it feels like something can happen in between. You might want to give your players a day-by-day break down after they set their path and made decisions, especially if they know where they are and where to go. Or, they might want to know every time something in the journey changes and make a decision. There's a swamp in the way. Go around or go through it? Lose time in one, lose resources because of combat and struggles in the other. If you go this route, I'd recommend at least knowing generally what the location is like. A map makes things far easier. Still I find opinions can greatly vary from player to player.
Did the new Dungeon Masters reading this get scared? Well, don't be. It doesn't instantly mean that all your players will hate your game if you get it wrong. Just be aware of the possible issues that might arise and be prepared to change your approach if your group likes things differently. Experienced Dungeon Masters also run into this when playing with new groups or players. They just know how to handle it due to their experience.
If you have a map in a pre-made adventure, you know roughly what the party will run across when setting a course and can describe it in ways that best suits your group. If you are making a map, that's where it gets difficult. You typically at least want to describe the general layout of the land, and possibly weather. If there is a change of location, such as rolling hills to desert, you'll also want to describe that. However, the big thing is to keep in mind when decisions will be made and these decisions often result in a time vs risk trade off.
Story or Simulation?
Part of this comes down to if you want a more simulationist or story driven experience. For some, role-play the travel can be the highlight of an adventure. Keeping an eye on food, trying to avoid detection, facing the elements, and still trying to arrive on time to their destination. On the other hand, the environment can be something to just skip past. Maybe nothing happened. A bear attack doesn't happen every time someone goes into a forest. Likewise, the trip can be unimportant. So make your choice.
When traveling between to locations, I find that there should be some sort of pressure. Whether it's a competing group trying to reach a legendary ruin first, weather getting progressively worse, or the threat of supplies running out, there needs to be a catalyst for tough decisions. It also means that the travel paces in D&D 5th edition start to have meaning where usually they don't. Without this kind of thing, a fast travel pace will very rarely be chosen. Why are your players traveling anyway if they don't have a reason to?
A common and rather effective method for getting players from one place to another is through a chase. Such a setup ideally forces difficult choices to be made and provides a sense of tension. However, we also need to put some complications in. Otherwise it'll just involve the party running away as fast as possible. There also needs to be some solution to the problem at hand. We can't have an unwinnable situation behind the players, forcing them to run forward at full speed right into an ambush they can't win. And at the same time, if the situation they are supposed to run from is unwinnable, the players should know. Looking back, a hilarious number of situations that were meant to be chases ended up as slaughters because players picked fights they thought they could win and failed.
Risk vs Reward
There is an idea of risk and reward when talking about going between two locations. Why wouldn't I explore every place I run across between here and my destination? Well, often times it's the risk of losing time towards our goal. Perhaps having that town indebted to me would be helpful in the long run, but I'll also lose time and give my enemy a head start on the important magic item stored in the vault of the city 4 days away. If I only have so many rations and no ranger, I might not be able to enter every ruin I come across either. Instead, I need to selectively pick them, mark them down, and maybe revisit them later.
This idea also comes back into getting lost. What does it matter if the party gets lost if there is no risk or penalty for doing so? Oh, it takes me longer to get to my destination? So what? The exception to this is when inadvertently finding locations. In this case, getting lost found me a new cool location, new resources and/or allies. However, without risk and reward the party may often just go at a normal pace because they don't want to deal with getting lost. Or they might go at a slow pace because they want to sneak. This decision depends on your party, of course, but the party will typically have one approach they use for everything. This can be fine in general, but there will be cases where you want that added pressure.
If decisions are being made there should be some outcomes at some point. Approaching a camp in the woods might allow multiple approaches. If we sneak, we might be able to get a sneak attack or poison their water. If we go fast, maybe we can get their before their hunting party gets back and use divide and conquer. Maybe we know they have hunting parties looking for us. If decisions are being made while traveling, they journey will probably be glossed over with a quick description. That's fine as it lets the party get to what they consider the good stuff. However, keeping in mind what choices the party has over their travels is a good starting place to make it more interesting.