Crete or Rhodes? Or there again Cyprus

I’ve been to all three of the islands you’re considering, and Rhodes is my favourite, followed by Cyprus. The wind is in the west of Rhodes, but it’s very welcome, and great for water sports in the summer. Rhodes town is beautiful, the street of the knights particularly, and Lindos is also very pretty - neither of them are in the west.

Rhodes has some lovely parts, but the south gets very hot in the summer and some of the resorts are a bit tired. If you want a real step back in time fly to Rhodes and take the ferry to Simi. It's a lovely little island but very hilly, but it has many of the features of Greece years ago, little tavernas in quiet bays.
Only did Crete once and found some bits overcrowded but great for historical interest.
Have you thought about Madeira? Gorgeous island, quite hilly but lovely gardens and scenery.
I think Cyprus will be very hot in summer.

You haven't mentioned Sicily, but you've probably been there. We've been 3 times and are planning to go again. Also mainland Italy is hugely varied. Clive Myrie has a travel series on Italy on BBC at the moment - every evening at 6-30.

If my memory is right I’m sure a friend of mine told me that either the north or south of Rhodes is very windy and is to be avoided! But I could be thinking of another island: it was a long time ago that she told me. I’m biased towards Crete because it is one of my favourite places in the world and I’d love to go back there. We used to go to Chania. I love all the old Venetian parts of Crete and there was always a gentle breeze which made the heat bearable. We went to Cyprus in the summer and it was incredibly hot but, from being disappointed in the place it grew on me.