5Astypalaia, for classic Greek scenes

Astypalaia is not among the most famous Greek destinations, yet this lovely Dodecanese island will win you over with the fairly affordable cost of living, the divine beaches and the chocolate-box architecture – look out for the white and blue Lady of the Castle church, the windmills, and the white houses with the blue windows in the capital; the latter populate the hill all the way up to the Venetian castle, forming clusters of real-life Monopoly houses (only white ones instead of red).

A true gem among the Dodecanese islands that should be explored before it gets discovered by hordes of tourists.