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).
Who hasn’t been spellbound by images of Capri’s electric Blue Grotto? This glowing sea cave impresses even veteran globetrotters — and it’s only the beginning of the island’s marvels. Ash-white limestone cliffs, hidden slivers of beach, a towering natural arch: It’s no wonder Capri has been a tourist hub since ancient Roman times. Tip: Climb up to the ruins of Emperor Tiberius’ Villa Jovis, circa A.D. 27, for a heart-stopping vista.
The advent of advanced computerized reservations systems in the late 1970s, most notably Sabre, allowed airlines to easily perform cost-benefit analyses on different pricing structures, leading to almost perfect price discrimination in some cases (that is, filling each seat on an aircraft at the highest price that can be charged without driving the consumer elsewhere).