Fly via Athens.
It is basically a difficult connection by ferry, at least requiring a few changes of ferries or stopping off for some days on intermediate islands, or trying to get rare inter-island flights, or via Athens.
A much easier idea would be to dump Santorini, and go to Nissyros an island with a volcano in the Dodecanese islands, a lot more characterful and far less touristy and over-hyped. Very easy to reach from Kos or Kardamena(Kos), same day connection coming from Bodrum no problem.
If you want other islands you have a choice of at least 10 easily accessible Dodecanese islands.
Turkey and Greece are different countries, and connections between them are not that easy. Coming from Turkey you also reach the Dodecanese, which are a different group of islands than Santorini and thus on different routes for ferry connections. Even though the distances may not look big on a map, ferry routes are run and schedules set up by demand. Travel between the different island groups are not usually done on a frequent basis, and they use Piraeus as a hub between these.
I am not sure whether Nissyros is the type of island you are looking for. Nissyros is small volcanic island, yet untouched by tourism but popular with day trippers from Kos (visiting the volcano). It has very few beaches but its wild beauty offers stunning views and remarkable walks.
Life is very laidback, but you can always take walks and discover the island on your own. It does not have a typical nightlife, but there are a few taverns where you can enjoy genuine Greek food and enjoy the peace. There are a few buses that can take you to the volcano and the main villages.
The main (and only) place for experiencing a choice of tavernas and some kind of shopping is the chora Mandraki. There is a hotel in the nearby fishing village Pali (4 kms from Mandraki).
-:- Message from TripAdvisor staff -:-
This topic has been closed to new posts due to inactivity. We hope you'll join the conversation by posting to an open topic or starting a new one.
To review the TripAdvisor Forums Posting Guidelines, please follow this link: http://www.tripadvisor.com/pages/forums_posting_guidelines.html
We remove posts that do not follow our posting guidelines, and we reserve the right to remove any post for any reason.