Anyone have updated experiences? Right now my travel plans are a blank slate. I am thinking about booking a trip for my wife and I to celebrate our anniversary around the end of June, so during the tourist season but not the really high season (I hear July/August are way worse).

I get that I can book Indie hotels at a fair rate, but I have 900,000 Hilton points, 500,000 IHG points and about 250,000 Marriott points. I need to start burning a bit. Finding places in Athens via Hilton/IHG is easy. Marriott has a lot of options on some of the smaller islands but when I look at availability I am assuming the 2020 calendar hasn't loaded yet? I mean some properties I see literally 0 rooms available (points or cash) for like 80% of the rooms. So I can see maybe nothing for May or June but I also see nothing for many other months.

What am I missing? If the 2020 calendar did not load that's ok but I'd expect to see "something" for say Sept or Oct this year during off peak seasons?

We are just looking for a getaway, so based on where we find available hotels we can island hop and piece something together. The Marriott reservation system only goes out til Mid June, so I know I could not even book late June, but I am just seeing how rooms become available and point costs to see what we could maybe pull off vs having to pay in cash.