Sometimes I like the hurky-jerky travel. In my big campaign my players have worked their way up to level 15 and are on the way to the story’s main villain for a final confrontation. I don’t plan to end the game, but probably ‘end’ the campaign by pivoting, allowing players to retire their characters if they wish, and deciding on a new story and setting in the same world. As they progressed it became harder to justify a challenging encounter on the road, especially after level 10 or higher and on paths they’ve already been on and where you wouldn’t expect to encounter a powerful foe. If they’re traveling between their current location and somewhere they have been before, I’m fine with treating it like a videogame fast travel, my players want to go to a different place to advance the story, not to deal with random encounters between here and there.

For lower level parties and for travel to places the party has not yet been or on a path they have not yet taken, I do a few things.

First, the party will decide how they’re going to get to the new location: do they set out on foot, or hire a carriage or even take a ship? (in my now-high-level campaign, the setting is a town and surrounding area at the edge of the continent, lots of ships available and the party has actually acquired a couple ships of their own) We often roleplay the party deciding their method of travel, and finding what or who they need to accomplish it, so if they’re hiring a carriage they will find the carriage company or a local citizen with a carriage large enough to accommodate the party. Once the mode of transport is arranged I’ll figure out an appropriate amount of downtime and ask each player if they have something they want to do/work on while on the road. The amount of downtime will depend on the distance they’re going and method of travel they’re using. There’s plenty of good downtime activities, some of my players with magic user characters will use the time to make scrolls, or copy from a scroll they found into their spellbook. If they’re traveling on foot or horseback there is obviously less downtime available to them to make progress on these activities since the bulk of their day is dedicated to the traveling, so my party likes to hire carriages or use a ship.

Once all of that is arranged I let them roleplay some conversation. If they hire someone to transport them they’ll often want to speak with that NPC at length to learn more about the area and what local lore they can. I also often use the actual travel as an opportunity to introduce a new character who is passing through, or let them cross paths with someone they’ve met before and give them an opportunity to catch up or learn the local news for the area they’re going to.

I used to do random combat encounters in the middle of travel sequences, and I still do in my spin-off campaign where the players are all goblins and kobolds because it’s a great opportunity for mischief and hijinks, but I try to not do that in story driven campaigns. An unexpected combat encounter in a travel sequence is jarring, slows the story down, and is just keeping the players and me from the game content we really want to be exploring.