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Specifically, dry descriptions of roads and cities and landscapes that have no mechanical or roleplaying value are the toughest of them all. For me, personally.

Though that may be more a sign that, in general, it’s important to prioritize useful landmarks and characterizing details in your intros and descriptions, so that you’re actually doing something in your monologues. If it’s boring the players to death, it’s probably boring the DM to death, too.

DM: Okay, this is fascinating, but maybe it’s time to head up to Cloudsdale?
Twilight Sparkle: Probably.
DM: Alright. You all climb into the hot air balloon. It’s a bit of a tight fit, but–
Rainbow Dash: What? C’mon. Me and Fluttershy can just fly up, right?
DM: You want to go ahead of them?
Rainbow Dash: Sure!
Fluttershy: That’s fine.
DM: Very well. The two of you fly the distance to Cloudsdale as the other four conduct the cloudwalking ritual and ride the balloon. The city itself is… Hmm, how to describe this… You know the Disney movie Hercules?
Applejack: Pardon?
DM: It’s like how Mount Olympus looked in that: Greek pillars supporting swirling clouds, but also rainbow waterfalls and… Wow, I just realized how absurd that all sounds.
Raibnow Dash: You could have sold that, like, a million times better.
DM: Hey, descriptions are hard.