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Athens or So. Spain in winter

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The trip will be in December. Before and after Italy, we can't decide where to go.

Day 1 Arrive Brussels
Day 2 Fly to Athens or Krakow
Day 5 Fly to Venice (second visit)
Day 7 Train to Rome (second visit. We want to be there for Xmas)
Day 10 Fly to Seville or Lisbon
Day 15 Fly to Brussels
Day 17 Fly back to the US

Will the other islands in Greece be accessible by ferry in December?
We are mostly interested in culture and history. Any suggestions will be appreciated. Thank you.

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