Oneways from Athens or Lavrion port towards Syros are ideal for bareboat yacht charters as well. Please note that the other direction would mean sailing against the prevailing northerlies. But also consider a oneway from Syros towards Kos or Rhodes, respectively a 7 day or 14 day sailing vacation combining both the Cyclades as well as the Dodecanese.
Syros and Paros can easily be reached via frequent ferries or hydrofoils from Piraeus - Athens, but to get back from Kos or Rhodes a domestic flight to Athens is advised. On most bareboat yacht charters you will return the yacht to the same charter base.
The popular yachts for bareboat yacht charters out of Syros are the typical mediterranean sailing monohulls: Jeanneau, Bavaria, Beneteau, Ocean Star. The multihulls are not readily available however. Trimarans are extremely rare and catamarans should best be booked a year in advance.
Consensus is that the age of the yacht should not exceed 4 years, preferably more recent. And only rent older yachts - < 4 years old - with reliable yacht charter companies who are specialized in bareboat yacht charters. Some trustworthy charter firms do indeed offer much older yachts but these are often totally refurbished and in pristine condition.
It is always possible to rent an instructor for just the first day(s) of your bareboat sailing vacation and it never hurts to study the first 5 chapters of my coastal navigation course :-)
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