The Greek islands are wonderful from late April to early November. For swimming, sun, and beach activities it's warmest from late May to early October.
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Secondly, the waters in Greece never get as warm as the Caribbean. The Mediterean is much cooler. You can swim in May, especially townards the end of the month, but expect cooler water.
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).
In the Greek islands, the sun will almost certainly be shining all day and the sea will be deliciously warm for swimming. In the southern islands, you can expect daily highs reaching 28ºC, falling to 24ºC towards the end of October.
Winter (November - March) is the low season of sunny Greece. While the big islands like Crete, Rhodes and Corfu entertain visitors all year round, the smaller islands wind down for winter. This would be a wonderful time to visit Greece for a laid-back holiday if you don't mind the cold.
We could say that, during these months, Santorini bursts with life! However, indications of warm weather start from the second half of April, during the Spring season, when there are moderate temperatures and the sea starts warming up, which makes it possible to have a swim, but not guaranteed.
Head to the Athenian Riviera in May and the sea may be warm enough for many to enjoy as well. Islands like Crete and destinations in the Peloponnese are rather balmy now providing an ideal time for lounging on golden sands and swimming in the aquamarine sea.
By far the warmest waters of Greece: The small island of Kastelorizo. Around the island one can find almost tropical sea life, including sponges, normally not found so far north. Next the east coast of Rhodes. The big island of Crete, further south, has cooler waters, caused by currents.
Weather in Greece in JuneYou can expect hot days and clear skies, perfect conditions for beach days or exploring the islands. You can enjoy the balmy water and escape the sweltering sunshine underneath beach umbrellas covering the shorelines as you explore the best beaches in Greece during June.
July ushers in Santorini's finest weather of the year, and it's the ideal time to get down to one of the island's delightful beaches for a long sunbathe or a swim.
Temperatures throughout Greece can vary, but May is a good choice for heat and sun in moderation. Temperatures: Average highs of 24 degrees celsius, average lows of 10C. Rainfall: Ranges between 13mm per month in Crete to 31mm in Corfu. Sunshine hours: Nine hours per day.
If you want to avoid crowds in Athens, time your summer travel for June or August instead of July. In the Cycladic archipelago (which includes Mykonos and Santorini), avoid July and August unless you don't mind crowded ferries and higher prices.
How Many Days in Greece: For most tourists, I recommend a visit of 10 to 15 days. This allows for a few days in Athens; a day trip to Nafplio, Delphi, or the Meteora; and a few nights on 2 or 3 Greek islands. Of course, trips of more or fewer days are possible. Can you visit Greece for only two or three nights?