A smile from one side to another on journey? (5)
I believe the answer is:
abeam
'from one side to another on journey?' is the definition.
(at right angles on a ship)
'a smile' is the wordplay.
'smile' becomes 'beam' (beam can mean to smile).
'a'+'beam'='ABEAM'
(Other definitions for abeam that I've seen before include "The way sailor goes across ship" , "neither fore nor aft?" , "across width of ship" , "at right angles to vessel" , "To the right or left of the centre of the ship" .)