There are few downsides, but one is that the Meltemi, a wind from the north that blows persistently for up to several days at a time and is liable to make the air feel cooler, can still affect your plans in September.
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Wind. Santorini is quite a windy island (average wind speed is 30 km/h), which mitigates the high temperatures.
Diaporos is never windy—unlike most of GreeceIt is an ideal destination not only for those who want to relax and kick back on one of its beaches with white-pink sands but also for those who cannot stand cold water or want to enjoy the sea in the winter time.
Obviously, the weather will play a factor in what you're packing — but if you're going to Santorini from late spring to early fall, you should be fine with mainly “beachy” attire. Think sundresses, several bikinis, shorts, and cute tops, along with hats and sandals.
On the coldest nights (mainly on the first days of the month), the temperature may drop to 10°C/50°F. On the warmest days (mainly on the last days of the month), the temperature may reach 24°C/75.2°F. The day lasts approximately 13 hours.
The average high's 26ºC in September, and Santorini's perfect for late summer sun as there's usually ten hours of sunshine from the 12 hours of daylight each day. Humidity's nice and low, but UV levels will be high so make sure you take plenty of sun cream.
Santorini beaches and water activities are warm and inviting from May to mid-October and at their best from June to September. Santorini in January (10% Crowded): Damp, cold, and windy (by Santorini standards).
Be warned that while early September will see all visitor facilities in full swing, but the latter part of the month may see hotels and restaurants reduce opening hours (or shut down completely).
The best months for swimming and sunbathing on the Greek Islands is from late May to early October. July and August are the busiest and most expensive months but are also the best for nightlife and beach parties.
Santorini is the top tourist destination in Greece and is world-famous for its unique natural beauty. The caldera with the white villages on top, the sunken volcano, and the charming sunset make it a popular place for vacation. In brief, we recommend staying 3 to 5 days in order to visit as many places as possible.
Mykonos will be windier than Santorini which is probably the better location for a 3 year old, but the beaches are black and gritty, unlike Mykonos sandy beaches.
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.