As a brief summary – the sailing season in the Med runs from around mid/late May to end of Oct. Generally, Turkey is warmer early and late season than Greece; and there is even a small difference between eg, our Dodecanese islands and the more northern Greek island groups.
The winds roughly follow the pattern of the temperature; they are strongest when the season is at it’s hottest; late july/Aug.
In SE Asia – the best time to be in our cruising grounds (Phuket, the Philippines) is the northern hemisphere winter. From late Nov to late May is the dry season in Phuket; in the Philippines, their sailing season lasts a little longer. It IS possible to sail in both places in the “shoulder” season, before the main monsoon rains set in; be prepared for short, sharp downpours; but it can still be lovely sunny and warm weather inbetween.