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Need Flight and Ferry Advice for June, 2017

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I need help on flights/ferries between Rome and Greece as well as inter-island flights and ferries for Santorini and Crete. Our ideal itinerary for end of May - early June, 2017 is outlined below. First time to these destinations and zero experience with Greek ferry system. I am finding that flight schedules are either limited or it is too early to book (except Ryan Air). I am holding FF seats from LAX to NAP, returning ATH to LAX after 16 nights. Could do this in reverse and could also reverse order of Santorini and Crete.

I have to secure our international flights but worried that I don't yet know all potential flight and ferry schedules yet. Are we likely to get the flights and ferries we need if we wait. I'm afraid to let the Ryan Air seats holding out for Aegean Air or others. Never used Ryan Air and the thought makes me nervous since they only fly on certain days so a delay could be problem:

Day 1: overnight flight LA to Naples
Days 2 - 5: four nights Sorrento (2 day trips to Pompeii and Capri)
Days 6 - 7 Transfer Sorrento to Positano. Two nights Positano
Days 8 - 9: Ferry to Salerno, Train to Rome. Two nights Rome (we've been to Rome before so short stay is fine. We just cannot find flights from NAP to Greek Isles below)
Days 10 - 12: Fly FCO to Chania, Crete. 2 nights Chania, 1 night Herklion
Days 13 - 15: Ferry Herklion, Crete to Santorini. 3 nights Santorini
Days 16 - 17: Fly Santorini to Athens. Two nights Athens
Day 18 Fly home to Los Angeles.

Advice on transportation is what I really need.

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