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Greece enjoys hot, dry and bright Mediterranean summers, cooled by winds, of which the “meltemi” from the northeast is the most notorious and most likely to upset Aegean sailing and shipping schedules.
Winters are mild, and in general the wet season begins at the end of October or beginning of November when it rain “tables and chairs” as the Greeks say. It begins to feel spring like in February, especially in Crete and Rhodes and the south coast, when wild flowers appear.
Any time is a good time to see some part of Greece. Winter offers wild, world-class clubbing in Athens, or gives hardy types a chance to play in snow and ski, or see archaeological sites in lonely splendor (a loneliness punctuated only by a few Japanese tour buses, the only consistent winter travelers to Greece).
Landscapes that seem barren in August are often wonderfully lush in January. Spring is a marvelous time for wild flowers and for participating in Greek Easter, the biggest holiday on calendar. Late spring or September and October are the best for hiking or traveling by car on the small unpaved roads in the mountain roads, since they tend to washout each year with the winter rains and are bulldozed again in the spring, although sometimes later rather sooner.
September and early October tend to be calm and warm without being stifling, the swimming is still excellent and the Greeks are laid-back. That leaves July and August the most popular months for sun lovers and people with children.
This includes the Greeks themselves, so it’s always the busiest time and prices are at their highest. The islands are the best from spring through to late September; after that the seas can be rough.