The Ionian is a popular spot, but for that reason I'd
personally not go. Certainly in-season as it has a reputation for being
extremely busy (make sure you’re in harbour by 3pm to get any space!) and often
very little wind...as in you needing to motor more than you sail. I've been
through on deliveries, but not for holiday...I don't want to spend my time
jostling for space in crowded harbours.
When I started, I by chance ended up going to the Argolic
which is sheltered by the mainland, so no big winds or sea, interesting and
quiet; very few flotillas and you can even go places and be the only yacht.
So for the past 5 years I've been back to http://www.greeksails.com/ - Greek Sails in
Poros. I started in 2007 doing a Comp Crew from Poros (with http://www.porosyachtingacademy.com/ - Poros Yachting Academy
– the Greek Sails sailing school) around into the Argolic and having a
wonderful time...great sailing, great sights and not busy. It was such a good
trip and I came back with such stories and photos that my wife then wanted to take
up sailing! As a result I did my DS and she did her Comp Crew and we went back
the following summer and did a bareboat back around the Argolic. Had a great
time, from the splendid isolation of Kipirissi to exploring the castle as
Astros, the remains at Mycenae or the huge Palamidi fortress at Navplion.
That proved so good we went back the following year and did
more of the Argolic, going down to Monemvasia which has to be one of the ‘must
visit’ places on this earth, and on around other wonderful spots…too many to
mention. Look at the Greek Sails ‘ http://www.greeksails.com/en_GB/greek-sails-sailing-area/sailing-peloponnese/ - Sailing the eastern Peloponnese coast ’ for
some ideas of the area and what we would have seen.
We have also sailed in the Saronic…north of Poros and
visited places like the ancient Greek theatre and Epidaurus and the temple of
Aphaia on Aegina from which you can look north towards Athens and the
Parthenon. Generally we’ve found the Saronic busier than the Argolic and often
very light winds.
With all this, my wife’s appetite for sailing has grown and
so last year we went out to the Cyclades and did a loop down the western isles
and this year we sailed almost to Turkey and back. So my wife has
gone from having never sailed, to this year doing long overnight passages well
out of sight of land for hours on end and her saying she rather enjoyed these
long passages and would quite like to try other night passages! That’s quite a
long way to come and I guess says something about a good introduction around the
Argolic.
So having found a good formula we have been loathed to break
it. Greek Sails is a small family business and so you deal direct with them.
Their boats are all well maintained and seem noticeably ‘nicer’ than many of
the larger operators boats. They’re also not emblazoned in some charter company
name. We have become good friends and so I’m probably biased, but I have pointed
friends in the same direction and they have all come back with similar great
experiences, so I feel I have some justification to be biased 
Anyway, hope this helps. There’s quite a lot of info on the
http://www.greeksails.com/ - Greek Sails website about places you can visit which may give you some ideas.
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