An outing with Juliet and Sally, perhaps (5)
I believe the answer is:
jaunt
'an outing' is the definition.
(I know that outing can be written as jaunt)
'juliet and sally perhaps' is the wordplay.
'juliet' becomes 'J' (phonetic alphabet: alpha, bravo, charlie etc.).
'and' says to put letters next to each other.
'sally perhaps' becomes 'aunt' (I can't justify this - if you can you should give a lot more credence to this answer).
'j'+'aunt'='JAUNT'
'with' is the link.
Can you help me to learn more?
(Other definitions for jaunt that I've seen before include "Outing" , "Short excursion for pleasure" , "Pleasure trip" , "Pleasure journey" , "Pleasurable trip" .)