weather should still be warm enough , the greek season finishes end of october so most place will be up and running [usualy start winding down end of second week october]
The weather last week in September should be OK. We were there last year at this time and it was certainly warm enough to be in shorts and tea shirt - days were sunny with only one day slightly showery. Swimming in the sea was fine too. Evenings were cooler and you needed a jumper. The west of Crete is really great if you enjoy typical traditional Crete mostly unspoilt by tourists. All Tavernas etc will still be open. The season for summer tourists closes at the end of October.
Enjoy
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