To sum up: a lot depends on your own stamina because island hopping means packing and unpacking, getting on and off buses and ferries. Limit your choice of islands to perhaps one or two less than you think you can manage. Maximise transport links to avoid backtracking or port-transferring and since you are traveling high season be aware that you will usually need bookings ahead at most places. It is possible to turn up on an island and not find a place to stay or have to make do with a third-rate option.
Increasingly since 1978, US airlines have been reincorporated and spun off by newly created and internally led management companies, and thus becoming nothing more than operating units and subsidiaries with limited financially decisive control. Among some of these holding companies and parent companies which are relatively well known, are the UAL Corporation, along with the AMR Corporation, among a long list of airline holding companies sometime recognized worldwide. Less recognized are the private equity firms which often seize managerial, financial, and board of directors control of distressed airline companies by temporarily investing large sums of capital in air carriers, to rescheme an airlines assets into a profitable organization or liquidating an air carrier of their profitable and worthwhile routes and business operations.

I’m traveling to Greece for the first time, and I’m so fortunate to be staying for about 9 weeks (peak season, unfortunately, I’m an educator and it’s summer!). I have ample time planned in Athens, and the Peloponnese (with rental car). Here’s where I need some help and suggestions. I have 5 weeks saved for the islands and I’m still trying to figure out how to spend them. I’m not sure if I’d like to cover just a few islands and soak them in a bit deeper with longer stays…or to travel at a quicker pace covering several islands in each main area (the Cyclades, Ionians, Crete-Rhodes Dodecanese, Eastern Islands) I’m an easy traveler and enjoy diversity. I crave spending time with locals and interacting with families – home stays at times, I enjoy the water and I’m an avid diver, I like hiking and exploring. Also, want to perhaps relax a bit – food/wine tasting welcomed). I’m excited about the trip and my ideas are racing all over. Do you have some ideas and suggestions to share? A rough sketch itinerary for Greece? Thanks so much!
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. 

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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).
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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