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Need meal and site advice for not often discussed Greek Islands & Places

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They are: Kea, Kythira, Monemvassia & Nafplion. They are not in my guidebook, or discussed much (if at all) on these forums.

We are going in early October, end of the major tourist season. We've never been to Greece or the Greek Islands before, so this will be a new adventure for us. I've already researched the "easy" to find cities and towns (Athens, Delos, Mykanos, Santorini, Crete, etc.), but my Fodor's Greek Islands book is completely dry on the above-mentioned places.

Kea will be our first stop after traveling from Piraeus. We'll be able to explore it in the evening, so I'm curious to know if anything has any thoughts on a tavern (or two) to visit, or some ancient building to explore?

We stop at Kythira mid-afternoon after cruising from Crete. We then have all afternoon, evening to explore the beaches or Chora (capital city with a castle), and find a place to have dinner. Any thoughts/recommendations?

Monemvassia follows Kythira, and would like recommendations on exploring.

Evening and overnight in the port of Nafplion. Would like recommendations on exploration and dinner spots, along with a bar or two.

Thanks in advance. Just trying to fill in the blank spots by you seasoned travelers!

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