Land north of Italian port, just about the most bleak (9)

'most bleak' is the definition.
Both the definition and answer are superlative adjectives. Maybe you can see a link between them that I can't see?

'land north of italian port just about the' is the wordplay.
I cannot really see how this works, but
'land' could be 'win' and 'win' is present in the answer.
'italian' could be 'i' (abbreviation for Italian) and 'i' is found in the answer.
'about' could be 're' ('re' means regarding or about) and 're' is found in the remaining letters.
'the' could be 't' (the is pronounced as a 't' sound in some dialects) and 't' is present in the answer.
The remaining letters 'st' is a valid word which might be clued in a way I don't see.
This explanation may well be incorrect...

Can you help me to learn more?