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Sailing in the Greek Isles in October

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We are planning a family sailing trip to the Greek Isles to celebrate our 30th wedding anniversary for next Fall. We would like to combine good weather, history, hiking and snorkeling for my husband and I and 4 adult children (all ages 23- 27). When is the best time to go and which islands would you recommend? We do not want to go during high season and have some flexibility. We tentatively have planned to go October 11-18. Is this too late or will it be comfortable and accommodating?

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