According to a previous post you arrive at 8am on June 9th, and I agree with kenko, you could catch a flight the same day instead of spending a night in Athens.
Wasting a day by spending a short night in a hotel near the airport (or in Athens) and waking up the next day at 3 or 4 a.m. to catch your Volotea flight is pointless
On the day of your arrival there are 5 flights to Santorini between 10.30 am and 1.30 pm with Aegean or Sky Express.
I know that Santorini and Mykonos are the favorite islands for tourism marketing (and it's very effective!), but going to Mykonos is not going to bring you much in terms of authenticity. Just like in Santorini, you will join the first hordes of tourists of the year who are victims of this marketing, plus those who regularly come to Mykonos to party. You will spend at least 30% more euros than on other islands for equivalent services.
It's your choice. But as kenko suggested there are others.
Paros, Naxos and I would add Amorgos, the island of the movie "The Big Blue"
From Santorini to Amorgos there are Seajets fast ferries daily at noon for €75 per person, but there is also the Small Cyclades Line "Express Skopetilis" ferry which runs on Sunday 12th for €11 (departs 11.30am ).
There are many videos about Amorgos, here is one:
https://www.youtube.com/watch?v=zQqb89OzurA
So you could arrive in Santorini on the 9th and leave for Amorgos on the 12th.
If you stay 3 days in Amorgos, you will have another 3 before returning to Athens.
From Amorgos you can easily reach Naxos. There are daily connections with the Express Skopetilis or Blue Star or Seajets, or Paros with Seajets or Blue Star.
This version of the Islands part of your trip would be as follows:
June 9: Landing in Athens and flight Athens-Santorini
June 10: Santorini
June 11: Santorini
June 12: Santorini to Amorgos (port of Katapola) with the Express Skopetilis
June 13: Amorgos
June 14: Amorgos
June 15: Amorgos to Naxos or Paros
June 16 Naxos or Paros
June 17: Naxos or Paros
June 18: Naxos or Paros to Athens
June 20 about your trip Ioannina-Meteores (Kalambaka) I do not think you will find trains (maybe others forum members have more info), but there are buses in principle every day for Trikala
https://ktelioannina.gr/en/index.html
From trikala you can take a train to Kalambaka.