Early days and just beginning research and planning, but . . . assuming Athens, some islands, maybe all the way to Thessaloniki (like I say, early days) . . . what about April in Greece?
Looks to be a popular time to go; all the RS tours for April are booked full.
When we went in late June, it was pretty and HOT; we were told had we come earlier there would have been LOTS more flowers to see.
We did the RS Greece tour in April and thought it was a great time to be there. Actually, it was already hotter than I had expected, but our guide said it was an unusually hot year and that it is usually a very pleasant time for hiking/walking. There were still a lot of spring flowers, and nothing was very crowded except a couple of the most popular sights. I can't speak for the islands though, as the tour covers the Peloponnese and Hydra. Have fun!
Be advised that Greek Easter weekend in 2019, April 26-29, is the busiest travel weekend of the year in Greece. All forms of transportation- planes, trains, long-distance buses, rental cars and ferries- will be booked solid, as will hotels, B&Bs, etc. Make sure you book well in advance and then re-confirm once or twice before your arrival.
April weather in Greece will be in flux, with a strong possibility for wind and rain. Late May is a better time to go. It'll be nice and warm but not sweltering. And the crowds on the popular islands will not yet have reached critical mass.
My only visit was last year end of April and beginning of May. There were some wildflowers and citrus blossoms, but a bit of heat in early May put an end to most of that. My first couple of days, I was glad to have a jacket, later on there were a couple of days that I found a little too warm for my comfort (low 30's). Wray went a month earlier and though it was chilly, there were more wildflowers. Even in early May the water was too cold for spending much time in the sea, though it was pleasant to loll on lounge chairs.