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Southern Europe tour including -the Eastern Aegean, from Athens to Istanbul

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We are a mature couple planning a two month tour of Southern Europe in September/October 2016. probably encompassing Portugal, Croatia, Albania, Greece and Turkey. The plan is to have a mixture of experiences ranging from cultural - exploring historic sites to lazing on pristine beaches. We prefer to stay in vacation rental property if in a location for more than a few days. If the stay is shorter we prefer smaller boutique hotels to large impersonal ones.
One the itineraries I found on Fodor's that intrigues is " Around the Eastern Aegean, from Athens to Istanbul" My first question would be how to travel to the various locales listed. Any suggestions would be greatly appreciated.

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