Ios
One of the most captivating epics of Ancient Greece is, of course, Homer's Odyssey. In this, Odysseus makes a long, harrowing voyage across the Aegean Sea, encountering a cyclops, sirens, evil witches, and other fabulous adversaries on each island at which he stops. The reader of this tale, then, would expect the Aegean and all its islands to be a treacherous zone of the world rife with danger and adventure.
Well, aside from the danger of spending all your money on the over-touristed and over-developed islands of the Cyclades, there aren't too many hazards the modern Odysseus faces. Once again, then, my expectations of Greece carved from my classical education were entirely misdirected. Well, at least somewhat - there were plenty of "harpies" on these islands :)
My first stop on my island-hopping jaunt about the Cyclades was the island of Ios. Ios was described in Lonely Planet as a party island for the young and cheap. Well, I can confirm that I felt, for the first time in my life, old. I was squeezed on all sides by 18-20 year-old Italian youths as I tried to meander down the few tight, narrow alleys that define the island's hot-spot. I went into a few bars and clubs, but came to realize, soon, that people-watching on the alleys was far more entertaining than actually going into the clubs.
I realized the next day that avoiding the area altogether and enjoying the island's beaches, windmills, and churches was far more rewarding. The bars and clubs were best left to the young and cheap.