There are various ways to enjoy a sailing cruise in Greece. Either on a regular charter yacht (bareboat, skippered charter or fully crewed charter) or on a luxury gulet motorsailer or superyachts. These motorsailers and poweryachts are naturally always fully crewed, with captain, deck hands, cook and hostesses. The gulet option is perhaps the finest option for a sailing cruise in Greece and the Greek islands. Gulets (also known as gullets, motor-sailers, caiques and goulettes) are the contemporary equivalent of the endemic aegean fishing boats. The present-day cruise version is newly built and offers all comfort and the luxuries for perfect sailing cruises. The only problem might be the availability, which is good around the Turquoise coast (think of Marmaris and Bodrum) and near the adjacent Dodecanese waters of Greece, yet which is rather poor in the rest of the Aegean Sea (also see my sailing and cruising guide for the possibilities in general).
For the rest of Greece the so-called superyachts or megayachts might be ideal for your sailing cruise and yachting vacation in Greece. These yachts - although lacking the charm of the wooden gulets - have the advantage of speed and allow you to visit several regions in Greece within a week.
There is however one downside to these types of sailing cruises (besides the costs) and that is privacy. If you have the ability to skipper a regular yacht yourself a Jeanneau Sun Odyssey, Beneteau Oceanis, Bavaria or other more common charter yachts would be ideal for you.
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