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How to plan three weeks of travel beginning and ending in madrid, spain?

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Help? I will be traveling with my 17 year old son for almost three weeks. I want to give him a trip that he will remember and love. Need to be cost effective too. The restriction is that we need to begin and end in Madrid. I have been told to buy eurp pass but am confused on which one and if I then need to buy the countries passes. Our thoughts were Spain, France and Italy. We are also scuba divers and would love to find a good place to dive and beach too. Do we book hotels and plan the route ahead of time? Along the way and call ahead? We are going in late July to early August. My daughter was invited for three weeks to stay at a friends house in Mucia. They will pick her up and return her to Madrid. Help? Thanks all

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