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Greece Travel Planning for 2015

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Hi,
Thank you all for the great information I’ve read on these forums. Now I am finally starting to plan my own trip to Greece in June/July 2015.

We plan to fly into Athens, maybe charter a sailboat for a few days then visit the Peloponnese and one island before returning to Athens. It will be me, my wife and 17 y/o son with one of his friends. We have been to Italy a few times and I do most of my own planning. We normally rent a car and try to hire a private guide for some of the more interesting sites. Ideally I would like to spend the first and last few days touring Athens (like so many recommend) then after a sailing charter, rent a car and spend a few days visiting the ancient sites surrounding Nafplion, then take a few days and drive to Sparta, Olympia , Delphi , Thermopylae and possibly Marathon. I’m really into history… Then off to Santorini for three or four days. We Plan to finish in Athens then fly home. Three weeks total.

My questions are:
1. When should I be booking the flights, hotel accommodations, rental car and guides?
2. Would it be a lot easier (pros and cons) to just use a Greek travel service (if yes, which one?) or do it on my own?
3. Also any recommendations or experiences on chartering a sailboat? (Not skipper myself, but maybe book a couple cabins on a small charter)

Thank you in advance for your help!

Steve

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