I have no real experience, but I think you don't really need to jump from one point to another if you dont "zoom in" too much on those points to begin with.
If you go the skill challenge way, I think the idea is to use the collective results as inspiration to paint broader strokes of their journey without each roll being something that happens in fine sloggish detail.
Ask your players to commit 2-3 skills they're proficient in that they think would be relevant to the journey and how they do that.

But mostly, the skills are just an excuse to ask the players what they do during the journey instead of coming up with everything yourself?
I've never done any of this, but offloading creative work to your players seemed like a really smart, lazy idea that I stole that from someone.

Obvious skills like Survival, Nature, Cartography, Perception. Maybe animal handling works for taking better care of horses? Maybe religion helps if they're travelling in the vicinity of a temple.
Maybe Stealth or even Intimidation can lower the odds of an encounter.
Asking the players which skills and how they use it, having them come up with the reason they think that skill would work kinda does half the job for you.

The point not being to roleplay each individual roll, but more like... using the collective results for a short "cinematic" between the places.
The rolls not being a fail/succeed, but more a degree of success kinda thing.
Maybe the DC is absurdly low, but a Survival roll of 10 means they forage just enough food without needing to hit their rations, while a 15 means they hunt a nice animal for a particularly nice meal.
Maybe they fail Perception, but suceed Stealth and nothing happens to them.
Might be easier to take the rolls (or even their passives) and narrate the travel in the past tense based on that. Taking the passives could make a lot of sense as it's pretty much a textbook passive rather than heat of the moment situation, takes less time but since it's much less swingy, that's not as helpful to narration.

Idk, maybe they get 3 out of 5 successful rolls:
You rode by day and camped by night for a few days. PC x survival skills allowed you all to subsist on the nuts and berries these plains have to offer, you even had an omelet one morning which was a welcome change from rations. PC y thinks they've done a good job of hiding your camp sites, maybe you were just lucky enough to avoid the roaming creatures of the night, but it certainly felt safer than camping in the open. PC z's flute kept you in good spirits and you've made good progress and you've arrived half a day earlier than you expected and you are well rested.

If they failed hard on every roll, they don't fail to travel and go back to square one that'd just be annoying.
They're just a bit late, hungry and tired from the journey. Which in itself... might prod them to the local inn, whereas they might jump straight into something a job if their travels went better.

Hell, depending on their level, you could even narrate a past mundane combat encounter: on the third day, a small pack of ghouls found your camp in the night but you were well prepared and made quick work of them.
Although, getting rid of them proved easier than the stench, you didn't have much appetite in the morning and you were happy to break camp early.

Pathfinder:Kingmaker crpg kind of has something like that for overland travel. With "roles" you can assign each character. Watch duty, Stealth, Foraging.
Maybe ask them what they do in their downtime too.

Maybe the warrior sharpened their weapons, and you can give them a +1 damage just for the next encounter.
Maybe the bard's performance lifted their spirits and they have advantage on their wisdom saves.
Cooking utensils already have rules for recovering more hp during a short rest, but that's not too useful in a longer travel, maybe they get a few temp hps instead.

Again, I've never done any of this, so use appropriate amount of salt.

Try a few things out, switch it up, but also ask your players?
It's perfectly ok not to bother with the mundane sometimes if you just wanna get to the next big thing. Fun is the only real rule.