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Greek Island Hopping in May 2014

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Me & the fiance are trying to plan our Honeymoon. We would like to leave for the honeymoon on May 11th and spend around 7 nights on the trip (including travel). Our main concern is weather. We were in Italy (Venice-Florence-Rome-Sorrento) this last May and LOVED LOVED LOVED it, but the weather was a bit colder and rainier than we had planned, which makes me nervous about Greece in mid May.

We definitely want our honeymoon to be a little more relaxed than Italy, we did the 4 cities with excursions in 10 days. Such a whirlwind but SOO worth it.. We both want to relax on a beach, but not the type to just lay there all day. We love food, WINE, and experiencing the culture of new places, which is the main reason we are leery of all inclusive Caribbean resorts. Would you think mid May could be too cold to lay out by the pool/beach? I'm nervous that I WANT to go to Greece so bad I'm almost forcing it for our honeymoon, but we live in Texas and won't always have the excuse or opportunity to go. Any other suggestions on places to go that time of year?

If we choose Greece I'm thinking only 2 Islands given the amount of time. Suggestions on which ones based on information I've given?

I turned to this forum planning our Italy vacation and found it so helpful. It opens your mind to things you would never have thought of. I truly appreciate all responses! :)

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