Short answer -- no y ou cannot do 5 stops and y es u are crazy to try. A perfect place to get some sound knowledge is not to expect an internet forum to give you a complete background on a country and how to travel within it. At some point, you really need to maybe read a guide (gasp!).
For example, you need to Drop Meteora AND Thessalonika .... you cannot just "keep going" ... via what? car? train? magic carpet? in Most of Greece you cannot rent a car one place, drop at another. There is only basically ONE train in Greece -- Athens to Thessaloniki. Plus, in most cases you cannot fly from island to island ... most flights are just from Athens to a given island and back. Greece is Not the USA.
Look at a Map ... here is one on the internet http://www.explorecrete.com/crete-maps/images/greece.gif Click to enlarge. See how far apart your destinations are??? I think you'd need to limit yourself to 3 places. I'd say RHODES - SANTORINI - ATHENS (and MAYBE delphi)... and do NOT put athens first. If you can immediately FLY to your farthest point ASAP upon arrival, don't even leave the airport,you will gain a half-day of your cruelly short stay. Therefore:
• SEPT 18- arrive 9 am - thru passport control/baggage etch by 11 AM ... There are flights to RHODES at about 3 pm and 5 pm, takes 60 mins, costs €61. Why not go across street, have long relaxed winey lunch at Sofitel hotel, doze in lobby, then check in to Aegean at 2 pm. (Flights to Santorini cost about 2-3x as much -- pricing by demand)
• RHODES -- stay 3? days -- There's a ferry M - W - F leaves RHO 3 pm arrives SANTORINI 1 Am. SAT.
• SANTORINI = Sat - Sun - fly Sun Nite to ATH
• ATHENS - Monday - Tuesday sightseeing Wed 9/26 outbound flight
.... Note: Why Rhodes? Are u a Crusader History Buff? Tell us what you know about it, and why it appeals to you.
re: Rhodes vs Mykonos: WHY Mykonos? (Parties are irrelevant, they are only hi season). Is that the only other Island u have heard of??? How about NAXOS??? Very Close to Santorini, totally different -- a hiking/exploring paradise ... lots of ruins, mountains made of Marble, hillside villages, amazing landscapes ... in 2016, Trip Advisors list of the 10 best islands in the WORLD named it as the ONE isle in the Mediterranean... do some research, find out why it's so acclaimed. Your itinerary then could be:
• SEP 18 - Fly to SANTORINI 11:55 (yes it will be expensive - but ferry is 7 - 9 hours)
• SANTORINI 9/18 19 on 9/20 - 2 hr ferry to NAXOS 9/20 - 21 - 22
• 9/23 - 11:40 AM flight to ATHENS (45 minutes Athen sightseeing 9/23 - 24 -25.
Anything more ambitious can only involve constant travel, minimal time to enjoy. This would give you Some chance to experience Greece. Remember, Magic Carpets haven't been seen in this area for at least 2,000 years.