I don't think you can be accused of being too hung ho about choosing the Cyclades.
Heres a quick run down of what to expect wind
The prevailing wind
in the summer is the one coming from North and is well known as the Meltemi "Meltemi".
It begins to blow in mid June, gets strongest in July and most in August and fades out by the begining of September. In July and August the wind blows at force 5-6 and may reach force 7-8. It may blow for 1-3 days or sometimes blow for 4-5 days in a row. During the rest of the months of the year the wind force is less (around force 3-4 Beaufort
TIP: In the Northern Cyclades (islands of Andros, Tinos, Mykonos, Kea, Syros etc.) it blows from North East.
In the Middle Cyclades (islands of Paros, Naxos, Kthnos, Serifos, Donousa, Amorgos etc.) from the North.
In the Southern Cyclades (islands of Ios, Milos, Sifnos, Sikinos, Santorini, etc.) it blows from the North West.
In the South West Cycladic islands (Sifnos, Milos, Folegandros islands) it is significantly less strong.
For some more info check out Yacht Charter Greece | Sailing Holidays Greece
Hope this helps