Once you've found yourself in Valsembor, make your way right. Go past the ferry and follow the coastline. You should encounter a very drunk person in a captain hat - talk to him.
(If you want to get one of the achievements then, right after the dialog with the slightly drunk captain, you must enter the ferry - you are next to the wooden stairs that leads to it, from there you must go to the bridge above quarterdeck, take captain's journal from the table and read it - more details can be found two subchapters later.
Turn right at the junction and use a single door below the signpost to enter the tavern. It turns out that the owner is the man who's helped Kate by giving her his wife's pass.
Once you're back with Kate, talk to the waitress wearing a folk outfit (she is polishing a table next to the door). After a short introduction, you'll learn that she is the granddaughter of Simon Steiner, and will give you the directions to his workshop.
Leave the building and turn right. Once you've reached the crossroad, turn left and follow this street until you've reached a miniscule flight of stairs. Climb the stairs - you'll see the shopwindow and the entrance to Steiner's workshop.
You can enter immediately and speak with the old man but if you are collecting achievements then you shouldn't do that yet. Head left from the workshop and go up the stairs that are in front of you. You are in the square near the station - go to the opposite side (deeper in the screen) and go down the stairs to reach the square in front of the town hall (where a protest takes place).
Go a few steps ahead and then go right until you can see the impressive monument that depicts an automaton that resembles Oscar - look at it (an active point on the automaton, but there is another one that allows you to hear Kate's opinion on this subject - on the road next to a girl). Thanks to those two actions done before the meeting with Steiner (reading captain Obo's journal and looking at the automaton monument) you are armed with knowledge that is necessary for getting this achievement.
Use the same path to return to Steiner's Workshop and enter inside. Speak with the watchmaker and, sadly, during the not so calm conversation the old man will feel bad. You must give him a medicine.