Isle of Wight town council's head is in debt (5)
I believe the answer is:
cowes
'isle of wight town' is the definition.
(I've seen this before)
'council's head is in debt' is the wordplay.
'head' indicates taking the first letters.
'is in debt' becomes 'owes' (I've seen this in another clue).
The first letter of 'councils' is 'c'.
'c'+'owes'='COWES'
(Other definitions for cowes that I've seen before include "IOW regatta location" , "IOW regatta town" , "IOW regatta venue" , "Where yachtsmen may be" , "where regatta happens" .)