My wife and I had a trip to Kalymnos for 3 weeks last year after a long trip in France and Spain. We were very impressed.
The climbing was brilliant and very varied. Good amount of routes from in the 5's to 8a. The grand grotte is absolutely fantastic... I would get on whatever route suites your grade there, and especially Aegialis if you are up to 7c.
The locals are very friendly. We found they could mostly speak English, and usually with an Australian accent, as many of them had Australian passports and/or had lived in Australia for long periods.
The best place to stay is definitely Massouri. You can rent a nice little apartment very cheaply. There is no need to book, especially in November (we went the last week of November and first two of december). You can walk to most of the good crags from Massouri.
In early november you should have no problems finding climbing partners, though they get sparse in later november and December, when Massouri shuts down for the winter.
The food is Greek, so not up to French standard, and the Coffee certainly isn't Italian, but the people are much more friendly than both, so I would definitely recommend the place.
If you are an 8a plus climber (more than 29), you might find it a bit limited, otherwise the place is brilliant.
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