Introduction
I recently got a very interesting question on Youtube. Where would you go in Greece, if you had to spend every month on a different island. Great question right? This was my answer!
1. January -Aegina

the perfect retreat close to Athens to wind down and prepare for the year ahead! Aegina is only 2 hours away from the port of Pireus by ferry. I always wanted to explore the Saronic gulf islands, as they combine two of my favourite things, lots of museums and archeological sites to visit with beautiful beaches.
2. February - Rhodes

one of the biggest islands in Greece, and home to the stunning medieval castles built during the time that Rhodes was under Venetian control.
3. March - Crete
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Mainly to witness the season change and enjoy the crisp spring mornings in the sea. There is something simply magical about Crete. I have lived here for a few months, and visited more times than I can now count, and believe me when I say, I will be back... a lot! March is one my favourite months to spend in Greece.
4. April - Corfu

I always wanted to experience the amazing traditions around Easter in Corfu. Colourful parades, and the peculiar custom of throwing clay pots from balconies (it sounds weird but check it out!).
5. May - Santorini

May had a lot of competition. It is pretty much the perfect time to visit every busy destination in Greece, as you get the amazing weather without the tourists (although sadly the pandemic may limit the tourists this year too). Santorini has quite a lot to explore, from beautiful vineyards, to the rocky beaches, and of course the most out-of-this-world sunsets every night.
6. June - Lemnos

Another all-time favorite. If you haven't eaten kalathaki Lemnou (the local feta like variety of cheese) you are missing out. Lemnos has incredible beaches that you can swim, windsurf, or kitesurf and at the same time allows you to hide away from the hustle and bustle. Also the food.. all of the food - trust me!
7. July - Kythera

This little island in between the mainland and Crete doesn't get a lot of publicity. I recently discovered how many tracks, waterfalls, beaches, and walks there are to explore and I fell in love. So definitely would spend a July here to avoid the crowds and to trek, hike, bike and swim all day.
8. August - Mykonos

because you have to at least once! I know what I said about peace and tranquility above... but you can't spend a whole summer without a bit of Cyclades!
9. September - Chios
Αnother hidden treasure of the northern Aegean. I would love to experience the mastiha harvest and taste the famous sweets of Chios. Mastiha is a type of natural gum that oozes out of mastiha trees. But here is the incredible thing - it is only produced by trees planted at the southern tip of Chios, and only there. It's an amazing product that tastes amazing, so if you don't know it already I highly suggest you check it out!
10. October - Hydra

Back to the saronic to welcome the winter softly. The allure with Hydra is how no cars are allowed on the whole island. I would love to experience that at least once, and instead bike around and read a lot of greek history books. The fascinating thing about the Saronic is how many battles were fought here during our war of Independence around 1821, but that's for the history nerds!
11. November - Naxos or Milos

It's hard to choose between the two! Both islands have a lot beaches (like Sarakiniko) and picturesque little villages to explore and have more remote as well as more touristy areas. Although the busy season is well over in November, experiencing the Cycladic spirit of life during any season is an experience. Which one would you choose ?
12. December - Syros

This island is known for it's amazing architecture. Greece is home to over 6,000 islands, and pretty much every single one of them have one special tradition to celebrate the new year and Christmas with, it would be a dream to spend a winter in some of more remote parts of Greece.
Conclusion
Finishing this list only makes you want to add more. There are so many more islands to explore, so I think next time I might have to make a list of one Greek island for every week of the year!