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Late August trip to Greece?

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I am getting closer to finalizing our plans for Europe.

I have some questions..

My current thought is to fly from San Fran to Rome and spend 2 nights there to recover from jet lag (utilizing United award miles). Then fly to Athens for 1 or 2 nights, then to Mykonos for 3 nights, than Naxos for 3 nights, then Santorini for 2 nights.

I have a total of 17 nights allocated for the trip.

Here are my questions (some may possibly be construed as "stupid" but never the less...)

Are Mykonos, Naxos and Santorini completely different that I should go to all three or will visiting 1 or 2 of them satisfy my need to "experience" Greece?

What is Athens like? It tends to have a somewhat negative reputation?

I usually like to visit 3 or more countries during a Eurotrip.

What might be a good option from a transportation standpoint to visit after Santorini?

Thanks for your thoughts!!!

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