You’d have to check the schedule for your specific dates but I think Santorini then Milos then Paros then Naxos and Athens would probably be the best order. 3 days in each sounds great. Or a small tweak: 2 days in Milos and then 4 days in Santorini (splitting time between 2 of the 4 caldera towns) or even 4 days in Paros (splitting time between Naousa and Parikia).
The only reason I came to Las Vegas from Washington State was to see CRISS ANGEL AKA: CRISS BLISS! TRULY WONDERFUL SHOW! THE IMAGE OF ENTERTAINMENT IN LAS VEGAS AND THE WORLD AND THE ENTIRE ATMOSPHERE MULTIPLIED BY THE GREATEST NUMBER 69 TIMES! AND THATS JUST THE 1ST TEN SECONDS! WOW! AM SEEING AGAIN 2 MORE TIMES TJIS MONTH! ALL MY MONEY GOES TO HIM. MONEY HE GETS IS JUST A TIP. BE IS PRICELESS!

Everyone knows the Venus de Milo (which has stood in the Louvre since the 19th century). Until recently, very few had heard of Milos, the volcanic island where Aphrodite’s graceful likeness was discovered. Those in the know jealously guard their treasured island, and especially its 70 (or more) beaches — surely the most diverse and dramatic coastline of all the Greek Islands.
A throwback to a gentler, slower, more elemental way of life, Astypalea is surprisingly easy to get to (daily one-hour flights from Athens). Every gap in the burnished hills frames a different view of Hora, cascading from the Venetian castle to seaside Skala. The scent of saffron biscuits wafts through the whitewashed lanes. Tucked beneath the battlements, Castro bar has a magical terrace that seems to float above the archipelago. 

The Greek islands have beautiful weather in the months just before and after peak season. It’s a great time to see the islands, save money, avoid the crowds, and still have great weather (though not as hot as July and August). If you want to see the super-popular islands of Santorini, Rhodes, Corfu, and Crete without the tourists then this is a great time to visit.
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