I have talked about famous races in a lot of places but missed Greece. One of the most famous there is the Aegean regatta, an ORC one. In August you can count with wind there and the region is beautiful (I will be sailing there this summer).
This year's edition will start in Lesvos, the Island where lived the a woman that would become hugely famous, passes by Limnos, Skyros and finishes in Skopelos.
Aegean Regatta 2013
Some nice images of some beautiful boats, specially this one
and lots of other nice boats: