Another good idea is to sail a oneway from either Athens or Lavrion towards Syros, with the prevailing winds from behind. This way you won't have to battle back to Athens against the northerlies and you will avoid the overlap - for the last day as well as the first day are spent in the same waters.
Similarly the oneway from Syros to Kos or Rhodes are fabulous itineraries for sailing Greece and discovering the range of beautiful islands in the Aegean Sea, also see my yacht charters guide for more tips - unsurpassed for sailing holidays and yacht rental also for the luxury crewed superyachts or catamarans!
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