My PCs are traveling up a 1000 ft+ cliff next session. Only one party member can fly so they'll be carrying the rest of the party up one at a time, with some difficulty due to her lowish strength. There are harpies, wyverns and other flying monsters in the area that might be interested in a slowly flying dire bat carrying something heavy. What would be a good way to run this?
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No one has Floating Disc? A cheese method may be to cast Floating Disc, then Rope Trick on the Disc, and have the party hide in the "pocket dimension" while the Floating Disc lifts the party.
Other than that, realize that ascending a really high cliff means constant fly checks, and one failure means death.
You could have the first trip up discover a cave entrance that may lead higher up the cliff [and some fights and treasures] so it's not a constant up and down monotony.
What i'm thinking:
The first trip up the Flying PC spots a several cave systems on the way up, and being a personal elevator is tiring, and convince the party that it may be better to try to find a way up through said caves, so they can rest up.
What they find in any given cave system can be determined by an Encounter chart. A Red Dragon Rookery!? A Clan of Dreugar?! An imprisoned Lich? An ancient dwarven elevator!?
Each system only goes so far up the cliff face- assume that one cave system layer is 20 ft.
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I had a huge dungeon with several entrances planned once. One of them was a cliff entrance that also happened to have kobolds guarding it.
Some kobold tactics I considered involved:
1. Drop boulders on party.
2. Use gliders and crossbows.
3. Literally catapult themselves at the enemy and grapple-murder them.
4. Some magical means of turning earth to mud, so that climbers would, well, lose their grip. (Not really applicable to your situation.)
5. The dungeon was HUGE, like I said, so it had small murder holes along the walls that the kobolds were going to use to shoot crossbows out of.
You get the idea. Even though the party is traveling by air, you can still use humanoid creatures if you wish.
With that said, let's focus on the flying monsters bit. Possible encounters:
1. Harpies attack - but not with the intent of murder. Instead, they're making Steal combat maneuver checks to take valuable possessions away from the party as the spellcaster carries people up to the top. This can lead to the party having to recover their valuables as a side-quest, and hey - they can find other adventurers' valuables, too!
2. Some jerk decides to use a magic whistle to make a Purple Worm or similar creature burst out of the cliff face and attack the flyer. But hey, this ALSO creates a tunnel they can navigate. Where does it lead...?
3. It turns out there is a portal to the Elemental Plane of Air here. Hostile Air Elementals are popping out nearby. Maybe there's an intelligent creature that wants help closing this portal?
4. There's a spell protecting the top of the cliff that keeps the winds MIGHTY strong and even produces a cloud that obscures vision when flying creatures get to close. The source of the cloud comes from a dragon nest very close by, as the dragon doesn't want anyone discovering her lair...
5. The cliff houses a griffon nest. Oops. Fight!
6. The cliff houses a griffon nest. The parents are gone right now, and there are a few eggs... Is taking them worth the risk?