My boyfriend and I will be traveling to Greece on August 1-11th. We have 10 days. Is this a feasible itinerary for a couple in their early 30s who want beach, relaxation, good food, boating, and some history? Fly into Athens have one full day there then fly to Naxos for a day and a half, Milos for 3 nights, then Santorini for 3 nights, then back to Athens for our flight? We chose Milos over Naxos at first, but after reading your blog it seems the beaches in Naxos may be better?
We are planning to come back at the start of September for 2 weeks to visit different islands for some beach and sun. To give you some background, we loved Santorini, Milos and the quieter / smaller places in Crete (Loutro, Falassarna, Samaria Gorge). We enjoy beach time, some hiking, site seeing, good wine / food and good / buzzy atmosphere at night for dinner / tavernas.

Nine weeks in Greece is a dream itinerary it certainly gives you lots of flexibility. As you seem to have Athens and the Peloponnese sorted, you just need to sort out your five weeks on the islands. What you need to realize, however, is that the islands are not all mutually interconnected, but rather they are ‘grouped’ – both administratively and from the point of view of transport routes. Here are the main groups.
Major airlines dominated their routes through aggressive pricing and additional capacity offerings, often swamping new start-ups. In the place of high barriers to entry imposed by regulation, the major airlines implemented an equally high barrier called loss leader pricing.[38] In this strategy an already established and dominant airline stomps out its competition by lowering airfares on specific routes, below the cost of operating on it, choking out any chance a start-up airline may have. The industry side effect is an overall drop in revenue and service quality.[39] Since deregulation in 1978 the average domestic ticket price has dropped by 40%.[40] So has airline employee pay. By incurring massive losses, the airlines of the USA now rely upon a scourge of cyclical Chapter 11 bankruptcy proceedings to continue doing business.[41] America West Airlines (which has since merged with US Airways) remained a significant survivor from this new entrant era, as dozens, even hundreds, have gone under. 
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