Overview:
-Estimated achievement difficulty: 3/10
-Offline: 27 (400 )
-Online: 0 (0 )
-Approximate time to 400 : 8 hours
-Minimum number of playthroughs: 5
-Missable achievements: Multiple, but each playthrough is ~ 1:30 hours
-Does difficulty affect achievements?: No difficulty settings
-Glitched achievements?: None
-Do cheat codes disable achievements?: No cheats

The Cave is a game, best known for his work on classic games such as Day of the Tentacle and the Monkey Island series. It is a puzzler, which involves you taking a selection of seven characters on a journey through a frankly strange cave. Each character has their own specific puzzle, and there are five standard puzzles to go through. The game looks beautiful, the voice over is entertaining, and genuinely funny in parts.

The puzzles are not too difficult to solve, but if you get really stuck, there are a few puzzle guides around the internet, but I really suggest solving them yourself, as this will be more satisfying and stretch out what is really a pretty short game. A complete walk-through can be found by Youtube user XCVii007r1, which I would suggest using only if you get really stuck (click on his name for the vids).

Each character has two endings, good and bad.
Bad simply requires you to trade your stolen trinket for your hearts desire and then leave The Cave.
Good requires you to hand back your hearts desire (it will take three tries before the man accepts it) and leave The Cave.
You'll gain two Cave Paintings per ending per character, but make sure you stay on the look out, as there are a total of 24 to find throughout The Cave.

Step 1 - Playthrough 1 (of 5)
13 achievements for 135

Group: Hillbilly, Knight and Time Traveler.

This is your main playthrough and you'll be dealing with the majority of the miscellaneous achievements along with the story based ones for Hillbilly, Knight and Time Traveler.
You'll also be getting the Cave Paintings for Hillbilly, Knight and Time Traveler so keep your eyes open!
Remember to steal the postcard before you leave the Gift Shop (and carry it through the rest of The Cave) to snag Shoplifting and Remorse.
At the Carnival you'll need to get fortunes for Hillbilly, Knight and Time Traveler from Xavetar.
Upon returning to the gift shop you should get the bad ending for Hillbilly, Knight and Time Traveler.

Miscellaneous achievements unlocked: "Well Done", "Shoplifting", "Fire in the Hole", "To Soothe a Savage Beast", "Creamed Corn", "Remorse", "Royal Buffet", "Weight of the Beast", "Smells Like Teen Spirit".

Story achievements unlocked: "What you Always Wanted", "A Midsummer Knight's Theive", "Funnier than a Burning Carnival", "Prevenge"

Working on: "Don't Fill Up on Fortune Cookies"

Step 2 - Playthrough 2 (of 5)

4 achievements for 70

Group: Hillbilly, Scientist and Monk

This is your do-not-die playthrough. I find this group to be the easiest for this. Remember you can quit-to-dash to avoid death (up until you respawn seems to work) but you'll lose a variable amount of gameplay.
Keep your eyes open for the Scientist and Monks Cave Paintings.
At the Carnival you'll need to get fortunes for Scientist and Monk from Xavetar.
Upon returning to the gift shop you should get the bad ending Scientist and Monk and the good ending for Hillbilly.

Miscellaneous achievements unlocked: "Who Wants to Live Forever", "Embrace Impermanence"

Story achievements unlocked: "Learn to Stop Worrying", "Grand Theft Karma".

Working On: "Don't Fill Up on Fortune Cookies"

Step 3 - Playthrough 3 (of 5)

Group: Hillbilly, Adventurer and Twins
7 achievements for 120

This is the last time you need to take the Hillbilly! You'll also have finished every bad ending and taken all 7 characters to the bottom.
Keep your eyes open for the Adventurer and Twin's Cave Paintings. (The trickiest painting is behind the bookcase in the lounge of the Twin's house)
At the Carnival you'll need to get fortunes for Adventurer and Twins from Xavetar.
Upon returning to the gift shop you should get the bad ending Twins and Adventurer and whatever ending you want for Hillbilly.

Miscellaneous achievements unlocked: "Walk Like An Adventurer", "Such Bad Children", "Don't Fill Up On Fortune Cookies"

Story achievements unlocked: "Win-win-win-win-win-win-win", "Corruption", "It Belongs in a Museum", "God Bless Us, Every One"

Step 4 - Playthrough 4 (of 5)
1 achievement for 10

Group: Knight, Time Traveler and Scientist

This is pretty much just a run-to-the-end playthrough. You've done nearly everything there is to do already. Based on a suggestion by DropDeadArtemus I've moved Hazardous Work Environment into this playthrough due to the high chance of dying.
Upon returning to the gift shop you should get the good ending for Knight, Time Traveler and Scientist.

Miscellaneous achievement unlocked: "Hazardous Work Environment"

Step 5 - Playthrough 5 (of 5)
2 achievements for 65

Group: Monk, Adventurer and Twins

Just make sure you get the good ending for all three of these, and you should be done with the game!

Achievements unlocked: "Redemption", "The Whole Story" (as long as you have picked up all the cave paintings!)

Mop Up

You should have this game maxed out, the only achievements you may have failed to get is the one for not dying, but after playing through a couple of times you should be able to get through pretty quickly and competently.

[x360a would like to thank ErrolErrolson & Corrupt x360a for this Roadmap]

The Cave Achievement Guide

Printable Guide
Show completed achievements
Show secret achievements

There are 27 achievements with a total of 400 points

  • Reached the bottom of The Cave.

     

    Should unlock sometime between trading your stolen trinkets for your prized possession and leaving the cave.

  • Got everyone out of The Cave without dying once.

    This is easiest with the Hillbilly, Scientist and Monk as their sections of the cave are fairly safe.
     

    • Just a few words of warning:
    • Avoid the guard with the gun in the Scientist's launch facility.
    • Stay still on the magic carpets in the Monk's temple.
    • Careful on that Ferris Wheel at the Hillbilly's carnival.
    • Watch out for the miner's dynamite.
    • At the zoo a good whack from the Crystal Cave Monster's tail will kill you.
    • The large hole on the desert island is very easy to fall into.
    • The do not swim under the boat on the desert island as you will drown.


    Remember, if you die (or are about to die), quickly hit the guide button and exit to dash. You may need to replay a large portion of the game but at least you won't be replaying everything!

    Don't try for this on your first run through. By the second you will have learned where you need to be careful.

  • Saw a postcard stolen from the Gift Shop.

    After returning to the Gift Shop with your three trinkets you'll need to interact with the Postcard Display and pick up the Postcard. The achievement will unlock when you enter The Cave proper. Keep a hold of this postcard! See Remorse.

  • Saw a postcard returned to the Gift Shop.

    Required: You to have stolen the postcard before leaving the Gift Shop.
    Eventually you'll arrive back at the Gift Shop. Simply place the postcard back in the Postcard Display.

  • Took all characters to the bottom of The Cave. (Player 1 only)

    (2)  

    Simply complete one run-through with each of the seven characters. This will unlock when you are exiting the cave with your last character.

  • Unlocked all Cave Paintings. (Player 1 only)

    You'll need both Corruption and Redemption and to have found every painting within The Cave, as these provide two paintings each. At least 5 playthroughs (if you don't miss any) are required. There are three character specific paintings in each specific characters puzzle, the rest you will see as you play through the game. A few may be difficult to find/reach, if you get really stuck, there is a complete text walkthough here that has all the locations listed.

  • Witnessed a hot dog cooked with the monster's breath.

    During your first visit to the Employees Only section of the cave you'll need to get passed the Crystal Cave Monster. Usually you would place the hot dog on the spike and ring the bell. For this achievement simply place the hot dog on the spike and jump over the pit towards the monster. Toasty!

  • Spied a King, eaten by a Dragon.

    Required: Knight
    After the King rushes off to talk to the Princess you just need to follow him back to the Princess's bedroom. That is one hungry dragon!

  • Got the Weight Guess scale to read 666.

    Required: Hillbilly, Knight and Time Traveler.
    Once you're at the carnival you'll need to gather up the Wrench, Sledgehammer and Barbell and - while holding these items - stand on the scales. Do this before solving the scales puzzle as once the puzzle is solved the scales will no longer work. Here is the math for you:

    Hillbilly - 175lbs
    Knight - 229 lbs
    Time Traveler - 194lbs
    Sledge Hammer - 15lbs
    Wrench - 3lbs
    Barbell - 50lbs
    Total - 666lbs!

  • All three characters killed by one Miner's dynamite.

    After pulling a couple of levers and causing a minor cave-in you'll come across a rather angry miner. You'll need your entire group blown up by the same stick of dynamite. The easiest way to do this is regroup everybody on the right of the bridge, and just wait for the boom stick!

    A couple of notes here. Firstly, if you're looking to get Creamed Corn then you should ensure the can of corn the miner throws at you is blown up by dynamite. Otherwise you'll have to take it with you and find another way of destroying it.
    Secondly, you should aim to get blown up before you begin solving the mine car puzzles. Once all three cars are delivered he'll stop throwing dynamite.

  • Pantomimed an ancient hieroglyph.

    Required: Adventurer
    Inside the Pyramid, go to the right then up the second ladder; on the right you'll see a picture of three Egyptians "Walking like an Egyptian". Simply stand your group in front of this picture and they'll do the dance.

  • Watched Mummy and Daddy's furniture get broken all to bits.

    Required: Twins
    There are two ways of getting this achievement. You can ride the dumb-waiter to the twins parents bedroom and jump on the bed two or three times until it breaks. Or, when you get the lockpick, you can break the shelf in the room with the open fire (press twice). Either way works fine.

  • Made all three characters smell like a dinosaur at once.

    Required: Time Traveler
    Use the time-machine to travel to the future and head to the dinosaur exhibit in the basement of the museum. Stand all three of your group in front of the exhibit and press the button. Stinky!

  • Recorded and played back the elevator music from the Zoo food court.

    While you're at the zoo you'll be fixing a tape recorder. Simply drop it in front of the shack that's playing some lovely music (three shacks left of the hot dog machine) so it records. Then drop it again near the Crystal Cave Monster so it plays.

  • Saw someone slip off a ledge in the Missile Silo.

    Required: Scientist
    Inside the Nuclear Launch Facility you'll come across a Wet Floor sign. Simply place it near a low ledge and then walk over the sign. Slippy! Be careful the ledge is not too high if you are trying not to die.

  • Got the bridge inside the temple to collapse.

    Required: Monk
    Keep hold of that feather! After solving the Monkey Puzzle you'll be riding on three carpets up past your hearts desires. On the right there will be an opening with a rope hanging down. Get your group up that rope and jump on the bridge at the top to break it.

  • Saw every Can of Corn in The Cave destroyed.

    There are two cans of corn you'll need to destroy. The first is where you meet the miner (see: Fire in the Hole) and will likely be destroyed by his dynamite. The second can of corn is on the desert island. Simply place it next to the explosive barrels as you're solving the barrel puzzle and the achievement is yours.

  • Got a Xavetar fortune for every character. (Player 1 only)

    Required: Everyone and (at least) three playthroughs
    When you're at the Carnival make sure to visit Xavetar's booth with every character. When the seventh gets their fortune this achievement will unlock.

    Warning! As noted by luke391 if you solve the Wheel of Misfortune then Xavetar's booth will deactivate. Get those fortunes before solving the puzzles!

 

Secret achievements

  • Saw every character's "good ending". (Player 1 only)

    (3)  

    Required: All seven characters good endings (at least three playthroughs).
    To get the good ending you need to trade a stolen trinket for your prized possession in the Gift Shop and then give the prized possession back. It will take three attempts before the man accepts it. Then just climb the ladder to leave.

  • Saw every character's "bad ending". (Player 1 only)

      

    Required: All seven characters bad endings (at least three playthroughs).
    To get the bad ending you need to trade a stolen trinket for your prized possession in the Gift Shop at the end of your visit to the Cave. Then just climb the ladder to leave.

  • Helped the Knight obtain Excalibur.

    Required: Knight
    Story based (cannot be missed)

  • Enabled the Hillbilly to burn down the Carnival.

     

    Required: Hillbilly
    Story based (cannot be missed)

  • Came ever-so-close to recovering the Sarcophagus.

     

    Required: Adventurer
    Story based (cannot be missed)

  • Stood by and watched as the Twins murdered their parents.

     

    Required: Twins
    Story based (cannot be missed)

  • Served as an accessory to the Time Traveler's murder of her enemy's ancestor.

     

    Required: Time Traveler
    Story based (cannot be missed)

  • Shared in the blame for the Scientist's act of mass murder.

     

    Required: Scientist
    Story based (cannot be missed)

  • Played some dubious role in the Monk's murder of his Master.

     

    Required: Monk
    Story based (cannot be missed)

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