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I am greek and have been there both in may and in October. Obviously can never be 100% but weather will be fine on both times. Are you going in the mainland or an island? Sea will be warmer in October as it's had the whole summer to warm up but nothing will be closed (well depends if you are going anywhere remote!)

Have a lovely time!

Western Crete (Alymyrida) is absolutely gorgeous. We went in August but I know the area is popular in May for it's magnificant Spring colour. Not sure about water temp but I would think it would be quite reasonable for swimming. Unheated pools may be a little too cool(depending on your tolerance levels - hubby doesn't mind swimming in the Baltic!).

There are places to avoid in Crete (Heraklion is not the prettiest and stay away from Hersonisos and Mallia) but there are other beautiful spots like Chania and Crete has delicious food.

Southern Peloponnese has lovely spots too and obviously, as the ad says, more than 2500 Islands to choose from :-)

We went to the Sani resort in mainland Greece in the first week of May a couple of years ago. We may have been lucky but the weather was fantastic - mid to high 20s and perfect for a beach holiday with small kids. Would have thought that it should be even nicer by half term.

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