This achievement requires a long series of steps, as do many others for this game.
In order to complete this achievement, you'll need a deck mostly compromised of triangles and circles, try to build it as you go.
On your first trip, you'll be able to play as normal, this will unlock important paths, once in Clifton you will meet either Klaus or Alexis, this does not matter, it only changes the story slightly. You do not need to succeed in either of their conversations.
On your second trip, what you need to do changes depending if you met Klaus or Alexis in the previous trip.
- If you met Klaus:
You will need to get at least one item from Pachenco before heading to Clifton.
Once in Clifton speak to Klaus, succeed at her conversation to advance the story.
You then have to speak to Alexis (he will become available) and succeed at his conversation to unlock the road to the Desert Oasis.
Head there and speak to Klaus, a successful encounter is necessary to continue
*You can use this moment to speak to Theo and Airat. You'll want to unlock the way to Long Gate as soon as possible by having a successful conversation with Theo, but you'll get another chance later if you fail on this trip. Collect a couple square cards to make this easier later, they will also be use in a couple of Klaus' conversations in the next trip.
- If you met Alexis:
You can head straight to Clifton if you desire, however stopping at Pachenco could help you build your deck.
Speak to Alexis and succeed at his conversation to unlock the path to the Desert Oasis.
Once there, have a successful encounter with Klaus to advance the story.
*You can use this moment to speak to Theo and Airat. You'll want to unlock the way to long gate as soon as possible by having a successful conversation with Theo, but you'll get anther chance later if you fail on this trip. Collect a couple square cards to make this easier later, they will also be use in a couple of Klaus' conversations in the next trip.
Return to Alexis if you want, this is not required.
Whichever path you got, you can now play as normal or head straight back to Bartow, this is a good time to get better fitting cards in your deck.
On your third trip, you will need to go to Bukam Boro, but you can try to unlock Long Gate first if you haven't yet succeeded. You will have other chances to do so later.
Once in Bukam Boro, speak to Klaus, you don't have to do this first however.
Succeed at her encounter and she will ask you to talk to Matilde. You need to have a successful encounter with her. (she will reappear as available if you already spoke to her before Klaus)
Once this is done, continue to play as normal or go back to Bartow immediately. Keep filling your deck with a good balance or triangles and squares, a couple accommodates can be handy. Keep a couple square cards as well.
On your fourth trip, you will need to go to Old Marae as quickly as possible, to avoid as many exhaustion cards as possible. However, you need to collect a few distressed cards (pink spirals), you'll need a couple for this trip. You can get them by talking to the people in Bartow or stop by a couple towns on your way to Old Marae. Bukam Boro, Aldhurst and Rimina are all on the way and offer possibilities to get this type of card.
Once equipped, go to Old Marae and speak to Klaus, a successful encounter is required to continue. Head to Anka (you will get the path from Klaus) and speak to her again.
A successful chat with her will continue the story.
Then, you can continue as normal or go back to Bartow. This is a good moment to get rid of your spiral cards and most of the squares.
On your fifth and final trip, go to Long Gate. If it isn't unlocked yet, this is your last chance. On your way there, you want to exchange any spiral cards and most of your squares back to circles and triangles (only if you already have the path to Long Gate unlocked, if not, squares are vital to do so). Keep a square or a couple accommodates, Klaus may still have a couple square cards, but this is uncertain.
Once there, have a successful conversation with Klaus.
You will need to do it a second time.
And there you have your achievement.
*You may be able to unlock the road to Long Gate in trips that do not mention it.
**A few conversations may allow a failure, but success is required in most of them if not otherwise mentioned.