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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Well, here's the good news. Yes, you can swim and safely sit in the sun until early December. There are some tips of course and best beaches where the waters tend to be warmer late into the year.
GREECE. Greece is home to some of the best swimming waters in all of Europe, and September is a great month to visit, with the weather and sea temperatures as perfect as can be (26.8°C/80.2°F).
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.
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.
The sea temperature is still warm in October and most days are sunny. Most businesses are open, despite the fewer crowds and, sure enough, you can find great deals in this off-season. The best time to visit Mykonos is October when the crowds have diminished, the water remains warm and rates fall.
September in Greece offers up some of the most beautiful weather of the year. The days are usually sunny and warm, with temperatures ranging from the mid-seventies to the low eighties during the day. Nights are still quite mild, and a light jacket or sweater is often needed for evening activities.
Greek islands which are smaller and less touristic have a shorter season, larger islands like Crete, Corfu and Santorini have extended seasons sometimes up to full year. Hotels have different opening/closing dates but the general rule for islands is that they open in April and close at end October.
The best time to visit the Greek islands, like Santorini, Mykonos, Corfu and Kefalonia (Argostoli), is in October when the weather is still warm and the crowds are few. The Greek islands are an all-year-round vacation destination, with temperatures ranging from 50°F (10°C) to approximately 100°F (38°C).
Tourist season in Greece is roughly Easter through October. 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).
And, yes, you can also swim in Santorini in October. In fact, the sea is sometimes even warmer than in June! Plus, you get a little extra when visiting the island's shores as October is a low-tourism month.
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.
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.
September is a great time to visit Greece. The weather remains hot throughout the month, sea temperatures stay warm, and visitors start to thin out as children go back to school.
Trousers & shorts: High-waisted shorts, culottes, and wide-leg pants should be on top of your list! Also, jeans are the safest option as they are always in fashion and go well with everything for a casual classy style. Sandals: Don't forget to bring with you a pair of flat sandals, ideal for both day and night.
Many people consider September and October the best time to visit Mykonos because the August crowds are gone, the sea is still warm and perfect for swimming, and the island has a mellow, laid-back vibe as the tourist season starts winding down.
While temperatures can heat up over the summer, October weather offers a slight chill in the air and can sometimes be warm enough to take a dip in the Mediterranean Sea.
The temperature of the water in any pool is likely to governed by the size of the pool, how deep it is and the time of year you visit. As greek-traveller says, the vast majority of the pools in Greece are only heated by the sun so if you visit earlier in the year they will be much colder than later in the season.
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.