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RS Tour Sept 11-24, 2017 connect w cruise to see 2 or 3 islands?

We would like to take a cruise at the end of our RS Tour to visit 2 or 3 islands for 5 or so additional days before flying back to D.C. from Athens. Has anyone done this and if so, which cruise line(s) and which islands? We prefer a smaller boat. Also 2nd question... we are looking into travel insurance, trying to evaluate whether it is worthwhile to take out. We have been abroad before but have never considered travel insurance before. Any recommendations as to good companies would be greatly appreciated.

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