Ahoy, Joannie! Thank you for question about the best time to enjoy a sailing vacation in Greece.
For an accurate answer, let's turn to someone who really knows Greece like the back of his hand!
We presented your question to Capt. Alexandre J. MATSAKIS. Captain Alex was born and raised in Greece and has been sailing along the Hellenic coast for more than 3 decades.
As you read his response, keep in mind English is not his native language, so please forgive an occasional grammatical slip on his part.
Here is what Alex had to say:
"Greetings from land of the Gods, Joannie!
Most requests for yacht cruises in the Greek islands are for Mykonos and Santorini… I sail in Greece since 30 years and I live in the center of Cyclades – on Syros island, in front of Mykonos.
My advice is to sail the Cyclades in May, June or October, and to avoid them in July and August because of the frequent strong wind "Meltemi" – able to spoil the best vacation.
I charter my 75 gross tonnage yacht IRINA for sailing in the Ionian islands in July and August (Ithaca, island of Odysseus, Kephalonia, Skorpios, island of Onassis) with one very nice sea in this period.
My other beautiful yacht ANATOLIE is sailing in the Sporades in July and August (the green islands of the movie "Mamma Mia" with Meryl Streep).
I do believe that giving the right advises is the best way to avoid problems and keep clients long time (some of them come 3 times on 3 different areas). We need to ensure the happiness of our customers (and that's a great job :-).
Example : why to send people on one crewed catamaran charters leaving from Athens in July and August ? They will have 2 choices : the Cyclades with big problems in case of Meltemi, or the Saronic islands with no chance to find place with a catamaran in their small harbors (except in Poros if lucky). Greece is not Seychelles or Caribbean!
So – we offer Cyclades cruises in May, June, September and October. Believe me, living in Cyclades, if we send our yachts to other very nice areas in July and August, is because there is serious reasons.