Moving to Greece looking for advices

Hello everyone, my name is Sonia, I am currently living in a seaside town half an hour from Rome in Italy. I love Greece so much its culture, the hospitable and generous people, the landscapes and all the rest. I've been to Greece several times, even if always in the islands, I was in Crete for two months that I loved very much. I would like to try to move and even if many people say that Greece is not the right country for the situation in place, I have a special feeling inside for this land. I would like to try and stay there for six months and then simply evaluate if it suits me. I would have this adventure with a friend who shares the same passion for Greece. We would not have any problems with job because we both work on the internet so we just need a Wi-Fi and a laptop.
Obviously not maybe on an island because the jump would probably be too big especially for winter. we would like a city not as huge as Athens, a town that also offers winter activities and a few more opportunities than the islands. Once there we will study Greek; we speak very good English and Italian of course. I have heard very well about the Peloponnese and I write here to ask if anyone has any advice, for example Kalamata could be a good solution? Not too small and close to other towns in addition to Athens just over two hours.
Thanks if anyone wants to answer
greetings from Rome 🤗😊
Sonia