This guide will present enough detail to get each achievement. It will require you to learn the game still, but you should have the direction you need to obtain any achievement you need. Note that this took me several days to compile.
[Quest] Death Note
Starting the game in your house, sleep in the bed. Not much later, you will receive a knock at the door. Go and answer the door. You will find a 'note' at your door. Go to the tavern (the building next door) and motion toward the counter to buy a drink. You will meet Casper, and mention the note left on your door. What you do from this point onward is up to you...
There is a bounty notice for Viscardi Amas, the bandit leader that Aramor finds opposition with. For this quest, you will need Manes (located outside the smithy to the far right). Reading the bounty posting, you now have triggered the quest. Hire Manes and set out for the forest.
Something to note, you cannot kill Viscardi while he is at the bandit camp. You must do something to enable the time-skip - so that he is in the settlement on the far side of the forest. You must, however, investigate the bandit camp before you can make it through the settlement.
If you have a spare coin, toss it in the well. This makes you 'lucky' - allowing you to traverse the forest without stepping into bear traps. Once you make it to the settlement, you must talk to the bartender. Buy a drink worth 2 or more coins. Doing this, she will open up and reveal Viscardi to you. Talk to Viscardi. Doing this leads him outside where he will be assassinated. Taking his sword as a trophy, return to Aramor and talk to the scribe in the right-most building in the city center. This is how you claim the bounty - netting you gold and the achievement.
[Quest] My Life for Aramor
Go to the barracks in Aramor (go to the city center and go left twice to find the building). A soldier will meet you inside, if you do not have the 'token' already (the token allows you to enter the barracks freely). Enlist the military. Upon completion, you are given a token, symbolizing your membership.
[Quest] I'm a Good Guy
This quest is related to the church in Aramor. You must go the Illiba route though... Taking the Illiba route, there is a boat at the docks of the abandoned city. This is only available before the time-skip. Travel through the jungle to the city. Go south to the docks. There you will see a boat. Accept a ride to Aramor, and you will find the scribe meeting all the new immigrants. Do not reveal your name. You will be given 3 options. Choose that you were a scholar. From here, go to the church (located at the city center). Enter and go to the left screen. Enter the left-most room to talk to the priest. After talking to him about work, follow his instructions and you will get the achievement.
[Quest] Strike The Earth
This quest concerns the blacksmith in Aramor. Ask about his services and offer to help. Doing this sheds light on what you must do, in which you must deliver precious ore back to the blacksmith. You will need a way to and from Illiba. There are multiple ways to achieve this, but I will only share one.
Note that you do not need to be in Aramor to start this quest. Simply gather the ore and talk to the blacksmith if you ever do meet him. Once he reveals his problem, you can give him the ore and he will reward you.
So, if you were in Aramor talking to him... If you don't have a bag already, the blacksmith gives you one. This allows you to carry the ore. As for a pickaxe, will find one in the storage room within the crypt. You will find another beyond the cave resting in a pit. (note that it is possible to finish this quest without one though)
It will be wise to get what coin you can - and what followers you can. (Mirada, Manes, etc...) To get to Illiba, I will take Captain Barlow's route. To do this, you must have access to the settlement beyond the forest. With 3 coins, buy the most expensive drink and learn about the bartender at the tavern. Doing this, ask about the captain too - revealing his name and giving you a map in total. Speak to the captain and he will take you once you are ready.
Now in Illiba, go into the caves to find the requested ore. You can either mine it from the cave walls, or if you don't have a pickaxe, you can go down the rope further in and locate a pile of ore down there. With the ore in the bag, you must return to the blacksmith to finish the quest. To do this, find the treasure within the fortress. Once you do this and escape, you will be offered the option to return to Aramor.
[Quest] Mmm... Sublime
Outside the walls of Aramor is a farmhouse to the right. Knock on the door and offer your services to Glen. You will be rewarded for helping him.
Note that doing this applies the time-skip - so depending on which ending you are going for, you will want to time this appropriately.
[Quest] Medium Game Hunter
Taking the Illiba route, there is a boat at the docks of the abandoned city. This is only available before the time-skip. Accept a ride to Aramor, and you will find the scribe meeting all the new immigrants. Do not reveal your real name. For this achievement, you must pick the farmer option. Doing this, you are instructed to go meet Wolf. He is located south of the city by the well.
Talking to Wolf, you are instructed to kill a deer. This is done by having a crossbow or having Manes with you. The deer is located within the forest. It is recommended to make a wish in the well before circling the forest. You will encounter the deer at random, so this might take some patience. If you wound the deer, you will have to wander around to find it again. Once you get the deer, deliver the body to Wolf for your reward.
[Quest] Lost and Found
This is Mirada's quest. You meet Mirada in the mirror located in the tower on Greyrock Island. You must examine the fountain twice to discover the mirror. Make sure you get her wand first, or else you won't be able to do her quest. You can either break the spell of the mirror by casting Dispell - or you can give the wand to her and she will do it. She then will leave for the portal room. Follow her and go into the portal she has created. This leads to the tower ruins in Aramor. This is where she explains her dilemma and her search for Andri.
To find Andri, you must do something to enable the time-skip. Once this happens, explore the bandit camp in the forest. Doing this, you can enter the settlement beyond the forest and get Andri from the shop there (located on the screen to the right). Andri will be in a cage, but all you have to do is examine it. If Mirada is with you, she will pressure the merchant to hand her over. Mirada must be with you to complete this quest.
[Quest] I'm a Bad Guy
This is the cultist quest. There are a couple ways of achieving this, but I will share one way. Start the game with Mirada and go to Aramor. Go into the city and enlist in the military. Get a weapon and search the chest for potions. If you have enough money, hire Manes and head for the crypt.
Encounter the cultists by opening the door to their meeting room. Mirada will have a conversation with them that leads to them offering a meeting with their leader. Choose to trust them and travel to the Illiba fortress where the cult leader resides. Once there, a fight breaks out where you must defeat the cultists. If you survive, the cult leader will have you work for him. If you refuse, the sentinels there will kill you.
Accept your quest to find Callia, and bring her to him. You are given a sentinel ally at this point. Exit the hallway and go right to the water room (underground dock). Examine the water. A cultist will ask if you are ready to travel back to Aramor. Before the time-skip happens, find Callia and release her. If the sentinel is alive, he will take care of everything after this point. You are then taken back to the cult leader. If the sentinel is not alive, Callia may run from you, in which you will not get the achievement by returning her to the cult leader.
Note that there is a way to travel between Illiba and Aramor by accepting this quest. This opens the game up a bit if you know what you can do with this.
[Quest] Fell Into Some Feelings
This is Aello's quest. This is only possible before the time-skip. Going the Illiba route, you may meet Aello and Siki. If you don't meet them in the jungle after being captured from Greyrock, you can find them at their camp. Once you are at the camp, Aello will be in the left tent (after passing through the first tent you find).
Speaking with Aello, she reveals that her lover has gone missing. Tell her that you want to help, and she will ask if you to help look for him while you are traveling. Aello then has Siki join you.
Travel north to the fortress. There are 2 ways you can enter. The main entrance is trapped, so unless you have a shield or it has been disabled - do not go through this way. Enter through the caves nearby. Through here, navigate your way into the fortress.
Once you find yourself in the main hall (there is a wing of stairs on your left and right). Go forward until you reach a stairway. Go left. Now reaching another hallway, look to your right and you will find a body on the ground. Examining the corpse, you will find a medallion. Take it and bring it back to Aello. She will recognize it and know that her lover is dead - finishing the quest.
[Quest] You're Safe Now
This is Siki's quest. Going the Illiba route, you will meet Aello and Siki (granted this is before the time-skip). The objective of this quest is not obvious until you find the mirror in the fortress beyond the jungle. A woman is trapped within the mirror. This is Siki's mother. Your goal is to free her and escort her to Aello (the huts hidden in the jungle).
There are multiple ways of breaking the mirror. One way is to find the hammer in the abandoned city south. Having Siki with you will make this easy because he can guide you through the jungle without trouble.
Note that Siki's mother does not fight. If you are in combat with her, she will likely die - rendering this quest impossible to finish.
[Quest] Bearer of the Ring
Joining the Aramor Military, the Captain will ask you to go and escort Von to the barracks. Given an official note, Von will take your visit seriously when you knock on his door. Doing this, you will go straight back to the barracks to meet the Captain. Doing this rewards you with armor and achievement.
Note that if you trigger the time-skip before getting Von - you will find the barracks locked and the ships in the harbor gone. Due to this, Von will accompany you.
[Quest] I CAN Kill You
This is Callia's quest. There is more than one way to achieving this, but ultimately, you must reunite Callia with her father, Viscardi. Regardless of how you start, Callia will be located in the Aramor dungeon before the time-skip. (else she won't be there)
You need a way to break the barrier containing her, which can be done in various ways. I used the Dispell spell, which you need the wand for. Before you do this, however, you need to know Callia's name. To get this knowledge, you must speak with the soothsayer. Having seen Callia bound, you can ask for information concerning her.
Also, if you do have the wand, free the soothsayer and search his cell. You will find the Heal spell, which will act similar to healing potions.
Now you have freed Callia. At this point, sentinels will come to get her. Fight them off and you will earn her trust. You must then find Viscardi... but as you will soon find out, the time-skip has taken place. Explore the bandit camp in the forest and make for the settlement. Once there, talk to the bartender and buy a drink worth 2+ coins. Talk to the bartender regarding the leadership of the settlement, and Viscardi will be revealed to you. Speak to Viscardi.
[Encounter] Lone Wolf
Enter the forest of Aramor and you will likely encounter this fellow right away. There is another way to spawn the wolf encounter, which will likely be noted elsewhere in this guide. As far as defeating them, you can be unarmed and rely on a follower to kill them.
[Encounter] To My Side
Traveling through the cave south of Aramor, you will find a giant tree. Entering it, there is a room with a large rabbit sculpture. Examine it... The statue curses you, spawning an evil spirit outside the city of Aramor. If you attempt to enter Aramor city, you will encounter the spirit of a dead hunter with 2 animal companions.
Being a spirit, you will need magic to defeat this enemy. The hard-counter for this is to have the Dreamcatcher. I defeated him by having Von with me. Once defeated, all the wolves still alive will vanish away - awarding you the achievement.
[Encounter] Avenged 7 Bold
After assassinating Viscardi in the settlement beyond the forest, the game causes you to flee. If you return, a group of bandits will attack you. It is recommended that you to have potions or some way of healing. Having Von or someone who can pick off the bandits fast is a must. As the title states, this is a group of 7 bandits.
Traveling south down the path below Aramor lies a cave. Beyond the cave is a giant tree. Housed atop the tree is a large bee you can fight. To reach it, you must wear armor to protect yourself from the barrier of bees that patrol the ladder. Due to this - Manes and Von will not help you. It is recommended to have a melee weapon and a ranged weapon for this fight.
Having defeated the bee, a parasite worm emerges. This fight is more about countering the enemy's stance.
[Encounter] Iron Giants
Win a fight against a group of sentinels. You will encounter this enemy a lot as you play. The crossbow is your go-to weapon for this fight. There are other ways of winning, but this is the most reliable way.
Manes also does rather well against sentinels. Callia, on the other hand, is weak against them.
[Encounter] I Am My Worst Enemy
This is the encounter with Von achievement. The easiest way to encounter Von is to travel with Mirada and visit his house. If you don't have the document from the military captain, Von will fight you. Another way to encounter Von is by playing the cultist route.
[Encounter] Bad Romance
A spirit roams bout the ancient battlefield across a select path on Illiba. This path is right of the tower you can pass through. You will need magic to defeat her, whether by your own hand or by a companion of yours.
[Encounter] Dark Covenant
This is the cultist group encounter you find in the crypt in Aramor. Note that the cultists leave after the time-skip (so you must fight them before this happens). There are a couple of ways you can fight the cultists. The first is to enter the crypt with Mirada. Make sure you don't wander in here right away unless you have the gauntlet. Another way to do this is to find Callia, and reveal this to Viscardi at his camp in the forest. Choose the first option and he will have you lead his men to Callia. Once you reach the cell, you are met by the cultists. You then have the option to aid either the bandits or cultists. This way is easier since you only have to defeat 1 cultist instead of 3.
This encounter is a large heat-radiating lizard. The lizard is slow and makes for an easy fight once you know the attack patterns. The lizard is located in Illiba within the caves, near the fortress transition. In the area where there is a lever on the wall, look for an area to the far right side of the screen. You will find a barred area with a lever planted in the ground. Toggle it to open the lizard pen.
[Encounter] All Hell Broke Loose
After defeating the skeleton king, you will encounter a group of 8 skeletons. Compared to the previous battle, this one proves harder due to the numbers advantage. You must get the remaining enemies down as fast as possible.
It is recommended that you have some form of healing, even if you have a good group with you. You want to have magic or some sort of blunt weapon like the hammer or crossbow.
Note that that bashing with the crossbow only does 1 point of damage, which only proves helpful when your other options fail you. Once you defeat all the skeletons, the achievement will be given.
[Encounter] The Necromancer
Depending on your preparation, this fight can be a breeze or a nightmare. On Illiba, there is a fortress that hides a treasure guarded by the undead. The Necromancer is the skeleton king and will have his minions to help fight you. To get to this point, you need a way to travel up a loose pile of rocks. The safest way to do this is having Barlow and his crew with you.
Note that Barlow doesn't do anything in combat. Rather, it is his crew that helps you.
There is a bar gate that blocks your path further in past the rubble you climb. Find the lever associated with it and toggle it. To start the fight, enter the treasure room and pull the glowing gem from the throne (Ashadeep). Defeating the skeleton king will grant the achievement.
[Encounter] My Dream Weapon
This encounter is triggered by examining the statue of Lin Emil, Sword Master (located in the fortress on Illiba). The statue will whisper to you about his challenge only if you have died and received the mark given by the grave-keeper in the death realm (you must pass through the dark portal twice after dying). Once you hear what Lin Emil has to say, a sword animates from his stone hands and fights you. If you have the gauntlet, you can defeat the sword with one move. If not, you need magic to defeat it. Once defeated, the sword becomes a loyal companion of yours.
[Encounter] Not This Time
Exploring the city center of Aramor, there is an office building for city officials. The door is to the right of the bulletin board. Enter and tell the scribe you are looking for a city official. For you to have a chance to defend yourself from the guards, you must have a companion with you that can fight. If you do not meet this prerequisite, you will be thrown into the dungeon. If you have Siki with you, he will free you from the dungeon. At this point, you are given a second chance to find a companion that can help you defeat the guards.
Note that there are 4 guards.
[Ending] Second Best
This is a cultist ending that takes place not long after achieving the I'm a Bad Guy achievement. Once the cult leader has Callia, he takes her to the stonehedge gate in the jungle. Once there, however, Von tries to stop you. If your sentinel companion is still alive, this fight is as good as over.
Note that this is a way to get the I Am My Worst Enemy achievement. After killing Von, the gateway activates and you follow the cult leader to the crystal core. Once there, Callia sacrifices herself to destroy the core. If you have the cultist mark, you don't have the willpower to do anything - granting you this ending. If you don't have the mark, you have a choice between this ending and another.
[Ending] Never Alone
This is Callia's ending. The way you would go this route will be similar to the cultist route mentioned previously, but you must not receive the marking from the cult leader. To do this, you cannot have Mirada with you. Instead, take her wand and learn what spells you can. Discover Callia in her cell, but do not break the seal. Go find the cultists in their meeting room and join the cult. They will take you to the cult leader, in which he will trust you to get Callia with a sentinel companion. Go get Callia and you will find yourself following the cult leader toward the gateway in the jungle. Note that he does not mark you when you do this.
Von will try to stop you. Once defeating him, you will make your way to the crystal core. Now... because you have not been marked, you can decide to obey and let Callia die, or you can attempt to save her. If you try to save her, you must defeat the cult leader. Once you do this, you achieve this special ending.
[Ending] Breaking Chains
This ending takes inspiration from the spiritual elements of the series. Although it is not proven that you are a fallen angel, there are parallels that relate to the notion that we are all fallen. Anyhow, this possible ending is made known to you by an angel.
In Aramor, there is a church building that houses an altar. You must offer a 'feather' upon the altar. To do this, there are 2 possible routes. The first is to talk to the priest and receive a blessing. Doing this spawns the feather that can be found in the tower ruins, south of Aramor. The second way requires you to have died several times (being touched by the scythe of the gatekeeper), which enabling you to hear the voices of statues (The only exception to this is the rabbit shrine located inside the fabled tree). Examining the shrine of Jabez Huxley in the fortress on Illiba, you are given a clue regarding the feather - as a possible route you can take.
So talking with the angel, you are given two choices - both lead to different endings depending on how you play the game. For this ending, we choose redemption. Choosing the other option, you are given instruction to defeat the followers of Dumoninos... the cultists and the sentinels (basically the We're the Good Guys ending route).
So, you are told to get a key. This is referencing the glowing orb that is protected in the Sacred Grove... beyond the forest. To reach this place, you must pass the Eye of Judgment atop the arc. Like in a Zelda game, you must shoot it with your crossbow. You can also hire Manes and he will do it for you. This is how I got past it anyways. Know that if Von is with you, he will not let you pass through the arc. Make sure you don't have him with you if you are going this route.
To obtain the orb, you must pass another test. You must be able to endure the pain of being stabbed by a holy flaming sword. The only way you can do this is by having either Mirada or Callia with you.
Obtaining the orb, you now need to go to Illiba. Yes, this is where the gate is, but you need Ashadeep. Go to the settlement where Barlow is and have him take you to Illiba. You will have to fight all the skeletons/etc, but it shouldn't be a problem if you have Callia, Manes, Mirada... Your chances are a lot better when you have company.
Now with Ashadeep in your possession, the gateway is located in the jungle. Make your way there and examine the center stone to place the orb. Once done, you are transported into another realm. This area is very small so once you talk to the guardian statue, there is little confusion about what to do next. Doing this, you find that there two possible endings if you have the gauntlet. You can use Ashadeep to redeem yourself, or you can use the gauntlet to destroy the stone and crystal core to receive a dark ending. Being redeemed grants you this ending, along with the achievement.
Note that if you have Callia with you, she will destroy the orb once you use it, trapping you in the outer realm. Also be sure to choose your words wisely when speaking with the guardian statue. In some cases, you need him to share details regarding what to do so you can proceed.
[Ending] Harbinger of Darkness
The way to achieve this ending is similar to the Breaking Chains ending. The twist is that you use the gauntlet to destroy the crystal core.
To obtain the gauntlet, you must die and enter the dark portal twice. You will then wake up on a tiny island where a statue stands near. Examine it and examine the 3rd star. The gauntlet will then be revealed to you. From here, you can go to Aramor (left), Greyrock (right), or Illiba (up). If you die again, you will meet a group of dark figures that will continue sending you back to destroy the crystal core. This is perhaps Gabriel's darkest ending.
[Ending] Mother's Boy
This ending is centered on Gabriel's past. To reach this ending, you must travel to Aramor. Your mother is alive and resides in Aramor. It isn't required that you speak with her in the beginning, but you will need to speak with her in the end to get the ending. Although there is one achievement, there are two sides to this ending.
To reach this point, you must have a companion with you. When this is done, go to the building adjacent to the church. The scribe will welcome you. Ask for a city official and they will soon after engage on you. Defeating the Aramor guards, you demand your exile to be lifted. Also, you have the choice to kill or spare them. When you are done, find and talk to your mother.
Note that you must do this before talking to her twice - else she will be closed off to you.
[Ending] Over the Horizon
This is Captain Barlow's ending. To achieve this, you must make it through the to settlement beyond the forest of Aramor. Obtaining his name and a map, Barlow takes you to Illiba to find a hidden treasure within an ancient fortress. You will be required to fight two groups of skeletons. Upon entering the treasure room, you will encounter the skeleton king. With him stands 3 skeletons. Once defeated, a group of 8 skeletons will spawn. They die easily to magic and blunt damage, but in large numbers, you die quite easily too. Make sure you have potions and appropriate gear for this fight. Once victorious, you and those alive will meet back outside the fortress. Barlow is impressed and invites you to join his crew. Joining Barlow rewards you the achievement.
Note that he gives you 3 options. You can go with Barlow, go back to Aramor, or stay on Illiba.
[Ending] We're the Good Guys
This is one of the core endings for the series. To reach this ending, you must get Viscardi to aid Aramor in their effort to defeat the evil forces brooding on Illiba. You learn more about this as you play - joining the Aramor military, speaking with the Soothsayer, taking a nap in the bandit tent (or in the abandoned city of Illiba).
This is what I did. At the start of the game (on Greyrock Island) I got Mirada's wand and learned Dispell. I then slept in bed and allowed myself to get captured, going to Illiba. Aello saves me, and I join them for safe passage. I do both of their quests before leaving Illiba. (was able to obtain the crossbow, hammer, sword, ore, etc)
I then took the immigrant boat at the city dock, which takes you to Aramor. Doing this, the scribe assumes you are an immigrant (lie about your name). He offers 3 jobs (or quests).
I chose to enlist in the military (top choice). I then left the armory, hired Manes, turned in ore at the Blacksmith's so I can buy more bolts (another quest), and went into the crypt.
I examined Callia's state and talked to the Soothsayer. After freeing the Soothsayer, I learned the Heal spell. I then freed Callia and fought the enemies that came after. With Callia with me, I went into the forest - to the bandit camp - and then the settlement. I bought Sunshine and learned about Viscardi. With Callia with me, I reunite both of them and mention that Aramor needs aid. We all leave for the ships and sail toward Illiba, where we fight sentinels. Doing this, we united with the Aramor Captain and Aello. There is one last confrontation within the fortress, where you will fight the cult leader and more sentinels. Having enough bolts for your crossbow, and Mirada's wand, you should be able to win. Once you do win, you receive a good ending.
[Ending] Make it a Date
This is an easter-egg ending that all takes place on Illiba. Understanding the markings, you find that this is a reference to an arcade game.
Beyond the battlefield on Illiba lies a peculiar grave with a skull - jaws open. An offering bowl lies at the base. This makes more sense after obtaining the medallion (for Aello's quest). To find this, find the fortress on the other side of the island - beyond the jungle. Once in the fortress, you want to go through the main hall and down the stairs. You will find another grand hall on your left. On the first screen, you can search left and right. On your left is an alter. On your right is a dead body. Search the body to find the medallion. Now back to the tombstone, examine the markings and insert the medallion. (token)
[Ending] Chosen Legacy
This is Von's ending. Being the hero of the 1st game, he has the opportunity to be the hero again. For this to happen, you must join the Aramor military. Once you meet the Captain, he instructs you to find and recruit Von. Once you do this, the captain tells you to meet everyone else at the docks. Before you make it to the docks, do all you can to prepare for the invasion. Keep in mind that you do not want to trigger the time-skip. Doing so will make this achievement impossible.
This route has several small skirmishes and one large one - all against sentinels. Make sure you have a crossbow and make sure you hire Manes. There are other preparations you can make depending on how you start this route. I chose to get Mirada's wand and make it to Aramor without her.
Defeat all the sentinels throughout the invasion. Doing this, you are led to the hedgestone gateway. There you will see the cult leader of the enemy. With an orb (key) in his possession, he powers the gate and disappears into another realm. If Von is alive, he puts an end to the conflict. If he is dead, however, and you have the ring, you do what you can to stop the cult leader. You then receive the ending and achievement. Due to the variable choices here, there are a few different flavors of the same ending.
[Ending] A Journey of Two
This ending is only available once Mirada's quest (Lost and Found) is complete. Once you do this, you are given several options (two of which allow you to leave with Mirada). Choosing this option, she will create a portal for you to enter. Entering the portal gives you this story ending.
[Ending] In and Out
When you die, you will find yourself in a outworldly plain. There are portals on your left and right. Look left and enter the light.