In reply to phil kujawa:
Some but not all the big Athens ferries stop at Kalymnos and the other little islands north of Kos.
If you like studying ferry timetables you may be able to work it out. In November there may oly be a ferry once or twice a week.
Flying to Athens you can't avoid a night in Athens, planes get in around 1600 and the last boat goes around 5.30 and Piraeus is a long way from the airport.
The little plane to Kalymnos is a bit susceptible to bad weather. The big ferries are basically mainline trains and they sail come rain come shine.