Cryptic crossword clue
Spend the summer, when retired, sailing round the Virgin Islands with a lot of drink  9

The most common and most likely answer to this crossword clue is the 9 letter word AESTIVATE

I've seen this crossword clue in The Guardian
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Buddy explains!

The straight part
We know that "Spend the summer" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case spend the summer = aestivate.
The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.
This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.

What does AESTIVATE mean?

AESTIVATE verb
  1. To go into stasis or torpor in the summer months.

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