The first thing you have to do if you want to make this trip, is to find some partners who have the same willings as you and feel that this holidays could be interesting. The second step, once you have found your partners, is to organize your trip, taking into account the cities no one wants to loose.
The best method to travel cheap, is to choose an starting point and an arrival destination, and if it´s possible, not to be the same one. If you have to take a plane, you have to know that prices might be the same or lower, if your starting and finishing cities are different. So, my recommendation is to research on the prizes of the flights! Kayak is a web that searches economical flights for you, and even compares itself to other webpages.
The next thing you want to do, is to research and read different types of reviews about cities you are staying in, and check the recommendations about that city. Remember that they may be written by people that have visited it, so they should be pretty useful. I personally recommend to plan your entire trip only after you have read this reviews, in order to organize the days you are staying in each city, becouse as you can understand, Paris has more to see than Toledo. In TripAdvisor you will be able to see reviews of restaurants, tours and hotels, all of them made by users. You can also read about places that you would not be able to find in travel guides.
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