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This question asks about how can a DM create suitable challenges for players with Aarakocra, who can fly at will. The question refers to challenges like pits and towers, which the Aarakocra can simply fly over. The answers mostly focus on combat (flyers have no cover, are easy targets, etc) and on the premise that only that player-character can fly, so he can climb the tower or fly over the pit, but the rest of the party is left behind.

However, either I have some misconception about flying or the answers have not taken something into account. I feel like I understand exactly where the OP is coming from, because I have made many dungeons with exploration challenges, pits, wells, vanishing walls, barriers, broken bridges, etc, that make my players come up with creative ways of bypassing them. Either by casting spells, or by using resources, or rolling for athletics and acrobatics shenanigans. My actual problem (and I believe the OP's as well) is, if we have a permanent flyer on the party, he can always just carry everyone over all these challenges.

Sure, there could be enemies someplace looking at the skies waiting to check if an Aarakocra is coming by, or enemies will eventually know the party has one, but that doesn't ring well with me. The party is low-level when this is an issue, they won't be that widely known. Enemies may vary, the don't always face the same group who will know that the party is coming with flight. Low level enemies are dumb, they don't account for possible means of entry from the sky.

In dungeons, specifically, if there is some pit which the party should make checks to go over, or use spell slots or shapeshifts or whatever, an Aarakocra just negates the resource usage for this, I might as well remove the pit and move along with it. Even if I had enemies on the other side waiting to attack possible Aarakocra flyers, the party would either not go that way (as they couldn't go ever over the pit while being mercilessly attacked by out of reach enemies) or they'd kill the enemies first from afar, and then have the Aarakocra carry them over.

I can maybe imagine that a flyer couldn't carry the party members over challenges, but I don't recall reading anything of the sort in the rulebooks. As far as I can tell, maybe he'd move as in difficult terrain, but that was it. So once more, how is exploration any challenge for a party with a permanent flyer, focusing primarily on the issue of that flyer being capable of carrying everyone over everything?

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You do have a good point here: if the group encounters a pit trap (or, as you say, a broken bridge, a well, or a chasm), and there isn't anything complicating the situation, then a flying character can just carry the group past that.

One counterpoint would be that most of these hazards probably weren't that interesting in the first place, because "grappling hook and 50 feet of rope" is standard adventuring gear, and that also lets a group bypass a pit trap / broken bridge / well / chasm.

But I think there are two deeper issues here.

One is that the function of challenges is not actually to make the players' lives difficult. The function of challenges is to let the characters show off how awesome they are by overcoming the challenges. If you narrate a sixty-foot-wide chasm, with a hundred-foot drop to sharp rocks and a raging river, and then the aaracokra says "okay, guys, I carry everyone across that" and the players are like "high-five! one less problem to deal with!", then it's not true that you might as well have omitted the whole thing. The aaracokra player got to use his power, and the group got to feel awesome, and that means you're doing a good job as DM.

The other issue is that most campaigns actually don't involve that many pit traps. D&D has a lavish, carefully built combat simulator, and most people that are playing D&D are having combats. If they're not having combats, they might be navigating social challenges, using stealth and trickery to outwit their opponents, or dealing with exploration challenges such as hidden doors, traps, or the vanishing walls and barriers you suggested. The pit traps you mentioned come up seldom enough that it's okay to let the aaracokra be awesome and resolve them.

It sounds like you might be running a home game, and you're expecting to offer the players a larger-than-average number of hazards that can be avoided by flying. If so, it's okay to simply ban aaracokras from your campaign. One sneaky way to do that might be to tell your group that you're playing by Adventurer's League rules; these rules do not allow flying characters at first level.

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There are concerns even for a permanent flyer at exploring:

  • Weight limitations: Aarakocras can't fly while wearing medium or heavy armors and that and their racial attributes favor jobs (classes) that use more finesse than strength. Flying while carrying their own equipment plus the heavy armored fighter/paladin/cleric is a hard task, if not downright impossible.
  • Splitting the party: The world of dungeons and dragons isn't a lenient one, danger is oozing from all the crevices of the places adventurers go. If the aarakocra player can carry most of the party or even if it's possible to carry all of them, he/she can't carry all of them at the same time. A 6m (20ft.) pit in a corridor that you can see the other side doesn't cause much concern, but a 45m (150ft.) chasm that can't be crossed in a single turn will have the party split in 3 groups several times. Too much can happen at these times and the party must consider if it's worth the danger to be left alone far away from any ally in a distance that most of them can't intervene.
  • Flying is dangerous: Just because you can fly, it doesn't mean you can always fly safely. Strong winds, low visibilty and other aerial challenges may discourage the flight path towards a more terrestrial approach. A burning structure has smoke all over it, if you leve the ground visibilty drops and you will have to hold your breath in the smoke; not a wise choice unless the last choice.
  • Hands up: Or more likely, hands down. An aarakocra flying while carrying a party member has his/hers hands occupied holding that party member. Do you really want to cross a dangerous place with your hands tied without knowing for sure that nothing will happen?
  • Sometimes isn't worth it: My group had all members capable of flying, they saw ahead of them a very wide boiling magma pool with low sharp rocks ceiling with a rock path in the middle of such pool. Magma was bursting to the ceiling everywhere randomly except at the small rock path. One tried to not use the path thinking it was a trap (it wasn't) and got burned (random chance, unlucky one) and pushed against the painful blade-like ceiling. There were monsters in the magma pool and they didn't overlook the trespassers. Teleportation was impossible in the whole place and they knew that. A bit extreme, maybe. They were level 18, they could handle that.

These were examples of when flight is possible, you can also challenge them sometimes with situations where flying over is impossible.

  • Tight spaces.
  • Low ceiling.
  • Underwater situations.

As the DM, you control the environment and all its challenges. The environment will always be as challenging as you want it to be.

PS: If nothing works for you after all that, throw a tornado at the annoying pigeon. ┐(´д`)┌

PS²: PS was just a joke, please don't do that for venting.

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    \$\begingroup\$ It should be noted that the DM shouldn't focus entirely on challenging the aarakocra, but allow them to be good at things too just like any other character. \$\endgroup\$ – Rubiksmoose Mar 11 '18 at 15:52
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    \$\begingroup\$ On the topic of Weight Limitations...I would also note this: They not only have to carry their allies, but also all the stuff their allies are carrying. It is not at all uncommon for High Str characters to be lugging around a massive amount of gear (tents, tools, heavy armor, multiple weapons, etc). A 170 lbs human wearing chainmail, a shield, and a longsword weighs 234 lbs. Unless you have Str 16+, you can't carry them. And that's NOT counting your own gear. \$\endgroup\$ – guildsbounty Mar 11 '18 at 17:32
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    \$\begingroup\$ @Rubiksmoose Not my intention at all. He asked ways to challenge a flying character, but it doesn't mean he should clip his/her wings all the time, just to prepare some actions that will keep the thing challenging to them when he wants to. Going against a player directly for nothing isn't good; my post script was just a joke. \$\endgroup\$ – Aguinaldo Silvestre Mar 12 '18 at 3:13
  • \$\begingroup\$ @AguinaldoSilvestre oh I want accusing you of that. But it's easy for such advice to sometimes be taken that way. \$\endgroup\$ – Rubiksmoose Mar 12 '18 at 3:23
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Outdoors, this is a challenge, and a flying character can bypass most obstacles. But then for scouting purposes, a 1st level Wizard with a normal familiar can do all the same scouting and exploration, and less conspicuously at that.

In dungeons, it's is fairly easy to not let it get out of hand. What's the wingspan on an aarakocra? How much room does he need to take off and to land? Unless a particular room is a huge hall, or a great cave, winged flight underground, or even just indoors, isn't going to have enough room.

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