Most motoryachts and certainly the gulets & motorsailers cannot be rented without skipper/captain, though a hostess, deckhand and cook are usually optional except for the larger vessels. The smaller motoryachts, catamarans and monohulls (shorter than 55 feet) can be rented bareboat if the guests have the appropriate sailing skills and enough experience. On the more advanced waters (the southern Aegean, especially the Cyclades) it is sometimes necessary to have two experienced guests on board otherwise bareboating will not be possible. Several criteria make the Cyclades more difficult to sail on: higher winds and waves due to a larger fetch from the prevailing northerlies and longer distances between safe ports or anchorages.
The Ionian and the Saronic on the other hand are very easy sailing areas and are ideal for beginners, flotillas and for families with little children. The Ionian can best be explored from Lefkas (or Nidri) and the Saronic Gulf best from Athens, Aegina or Poros.
See my yacht charters guide for more information about planning the perfect sailing adventure in Greece.
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