But the most important factor is whether the guests will be able to sail themselves in a safe way (with respect to both the crew's health and the yacht).
The highlight of many sailing holidays is a visit to the Ionian islands of Lefkas, Ithaca and Zakynthos or in the Aegean the islands of Santorini, Amorgos, Paros, Naxos etc. Moreover in the Dodecanese the highlights are Kos, Rhodes, Symi and Nisyros and there are beautiful itineraries possible in all of these Greek areas. Note however that combining these sailing regions is first unnecessary (there is so much to see in for instance the Cyclades alone) but secondly the distances between the regions would mean sailing for months rather than weeks! It is therefore highly recommended to sail one area per holiday (if less than 2-3 weeks) and thoroughly enjoy and explore all the interesting islands instead of racing past a gem to reach for another gem. Also, night sailing (necessary to cover large distances) is often forbidden in the bareboat contracts. On crewed charters (motor yacht and gullets) this can be ordered but is not standard.
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