Cara2012 has indicated that this thread is about Santorini
Your first itinerary needs some caution on a logistics point of view because ferries along those routes will run 2-3 times per week on October. Usually Western Cyclades consortium and NEL lines run many of the routes in the area, their ferries are not as huge or as new as the Blue Star ones, but are quite large car ferries, stable and reliable. there might be some Sea Jets along the Santorini-Folegrandros routes too, those are smaller catamarans, keen on cancellations in case of windy days. Too early to have the official schedules announced.
Second itinerary is much more feasible in terms of travel logistics. Santorini to Naxos is a daily route on the very reliable Blue Star and there will be a couple of other options too, Naxos to Mykonos will be a couple of options per day, occasionaly through Paros or Syros, most likely direct, some on fast ferries and catamarans, a couple on Blue Star and NEL lines.
As I believe I mention on your previous post, Folegandros holds only 500-600 population, Milos aroud 5000 and those islands have a much shorter season than your islands on itinerary 2 . I do not know when exactly on October you plan to visit but I doupt you will find many cool bars or people around you on Folegandros and quite likely Melos on October, especially the latter you move into the month....
Cruise ships are a thing of Santorini and Mykonos as are crowds on October too. You will have no such issues on your other destinations. On October teenagers are back to school.
Do note that 3 nights somewhere is 2 full days, 2 nights=only one full day. Why go all the way somewhere just for one or two days?
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