Captain-T a écrit:

Hi. My wife and I are thinking about a 4-week cruise from Kos to Athens
in June.

I'd rather do the contrary : Athens to Kos.
From Kos to Athens in June, you should mostly experience N-W winds, i.e.
right-in-the-nose winds all along the journey. Be aware that these winds
can be very strong around certain islands and that the Mediterranean is
not the Atlantic ocean (waves are shorter and more difficult to manage
for a similar wind force).
Except in case of a big piece of luck (no Meltem wind in June this
year), this will be a tiring trip with the risk to stay blocked for some
days in a island or another, waiting for the wind goes down. I have
escorted many boats (including mine) from Turkey to Athens in this
season and this happened to me several times. Conversely, Athens to Kos
should be a very pleasant trip with the wind (and the sea) backward most
of time.

We have sailed throughout BVI and in the New York area, but
this would be our longest bareboat to-date. Does anyone have experience
and/or information about the best charter companies,

In this area, the best charter companies are to me Kiriacoulis (Greek)
and Sunsail (international). I don't now whether they operate in Kos
today. Avoid small Greek companies, they are unsecure (specially when
you are depending on precise dates for flights).

times of the year,

End of May-very begining of June. End of September-very begining of
October (with shortest days than the former period).
But in 2005, there have been very strong winds in June and a pleasant
wheather in July and most of August, again strong winds at the end of
september and also, some days, till the end of October. This is unusual
but this can happen.

and level of difficulty we are likely to experience in Greece?

Navigation during the day is not difficult (very few dangers, no tides,
no strong currents). The only difficulty is the wind (and in some places
the sea) when you go North or North-West and night trips (very scarse
and tiny lights, a lot of speedy ferries and cruise vessels).

Appreciate any tips/advice.
Thanks very much for any pointers!

You're wellcome

--
Peio