For this trophy you need to wait at the bar of The Stars At Night pub and The Seventh Whistler pub. I waited for 3 minutes in each location (to be 100% sure that it worked), the stars pub is in the first area you come to, where as the whistler is in the next village towards the train station.
Here is a video, just for reference.
Credit for the video goes to PS4Trophies from Youtube.