I think that’s a great plan. Santorini is a must and Milos and Naxos are two islands that have both great beaches and lots to do and see away from the beach. Renting a car and exploring the interior villages of Naxos is a must-do and so is a boat tour around Milos. If you’re willing to cut Athens to 2 days, I would recommend Santorini 5 days, Milos 3 days, Naxos 3 days, and Athens 2 days.
Where to stay in Crete: A 300-year-old hamlet surrounded by olive groves, Kapsaliana Village Hotel exudes peaceful authenticity. On a sandy bay just beyond Chania, Ammos Hotel smartly combines Scandi chic with a child-friendly vibe. Blue Palace Resort & Spa beats the (stiff) competition in Elounda with its spiral stone Isola Beach Club, thalassotherapy spa, and boat trips to Spinalonga island, a national monument just across Mirabello Bay. 

A complicating factor is that of origin-destination control ("O&D control"). Someone purchasing a ticket from Melbourne to Sydney (as an example) for A$200 is competing with someone else who wants to fly Melbourne to Los Angeles through Sydney on the same flight, and who is willing to pay A$1400. Should the airline prefer the $1400 passenger, or the $200 passenger plus a possible Sydney-Los Angeles passenger willing to pay $1300? Airlines have to make hundreds of thousands of similar pricing decisions daily.
I need to finalize plans for a mid-June trip, looking to stay 9-10 nights. Traveling with my wife and two sons (24 and 16). Definitely want to go to Santorini, Mykonos and Athens. Was considering 3 nights at each, but after reading on your site, I am thinking about stealing a night from Athens and spending 2 nights at Naxos. We want to see the major sights in Athens, can we do that in a day? Any comments on the itinerary given our group is welcome.
Yachts moor in the deep, sheltered harbour of Vathy, or Kioni, a miniature port where you’ll find Spavento, the perfect pier-side café-bar. Go any time of day or night for ice-cream sundaes, excellent cocktails, and a soundtrack to make your heart sing. Ideal for low-key family holidays or retreats, rugged little Ithaca is somewhere you can still disappear.
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