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Late September Greek Island Honeymoon 1 week plan

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Flying from Chicago, want to make the most direct, time efficient trip to Greek Island. The time frame may allow 1-2 destinations instead of spending too much time on transportation.
Thinking about Naxos or Santorini vs other suggestions for a memorable trip. Main interest include unique sightseeing destinations/landscape, beaches and possibly hiking.
Hopefully not overcrowded with tourists at the time.
Budget of $2500-3000 USD per person including flight, hotel, and tourism.

I'm open to suggestions and feedback. Thanks.

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    Naxos and Santorini would make a good combination as they are quite different islands. We found Folegandros quite romantic with dramatic cliff and sea views and would love to go back to this great family run hotel:
    http://www.polikandia-folegandros.gr/

    The ferry runs between Santorini and Folegandros and also between Naxos and Santorini, perhaps you should check timetables before deciding either way. This website is good for fares and timings:
    http://www.goferry.gr/

    I'd suggest staying in Oia on Santorini, we've stayed there and also in Fira and Oia has a more romantic, quieter atmosphere but still with lots of places to eat and it's only about 20 mins by bus into Fira.

    I would check exactly how much time you would have on the islands before deciding between one island or two. So you arrive in Athens, then either fly to another island or get the ferry. That's when your time starts. Take off time at the other end to reach Athens and fly home and you may only end up with 3 or 4 days actually on the islands. If that's all you have I'd stay on one island and really enjoy it, rather than adding in more travelling, checking in and out of hotels etc.

    We have been to Greece quite a few times, in early October the season was really winding down, with few tourists so I guess late September it will be getting quieter.
    Kay

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