Is it windy in Crete during August? You're unlikely to experience any strong winds. Expect a gentle breeze that increases to moderate at times during August. With moderate humidity, any breeze will have a welcome cooling effect.
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The mountain ranges of Crete affect the weather in a couple of ways. First, they create a physical barrier for the winds from the North. This means that even when the north coast is uncomfortably windy, the south coast may be calm and pleasant.
Peak season is summer, when Athens is packed with tourists, and hotel prices can be high. July and August are the hottest. The best time to visit is late spring (May) and fall (Sept–Oct). It's pleasant, with comfortable weather, no rain, and smaller crowds (except during holiday weekends).
The answer obviously depends on the size of a boat and the size of the waves, but in general, wind speeds over 20–33 knots (around 28–54 km/h) are considered too windy for boating. At this speed, almost all sizes of boats are greatly affected and smaller ones may even be in danger of capsizing.
It can cool off at night more during this season, so make sure you are prepared with a warm sweater, especially in the mountainous areas. Winter in Crete brings colder weather to much of the island, with snow in the mountains and rain in the rest areas, but still, sunny days are very common.
South Crete is generally a couple of °C warmer (but water temperatures are roughly similar). The east of the island, has less rain than the north and especially the north-west.