{Spoilers ahead for Max route} I seem to have encountered a strange glitch where Toby is both on and not on the journey at the same time. Following his confession to Max, I unlocked his friendship stat and got the message that the route could branch to involve him, but then at the trial when it was suggested he join us in exile he backed down. He was not present during the travel scenes, but then he was at the church in Firenze. He was then missing again in the camp scene that night, but then Max suggested that Toby be involved in exploring his feelings towards the player.