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Help Request - Planning a 8-10 day trip to Southern or Eastern Europe

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My girlfriend and I are trying to plan an 8-10 day trip to Europe for this coming August of 2013, but are finding ourselves overwhelmed by the options. We have both been to, and loved, Spain(especially Madrid) and would be open to another trip to Spain, but are also interested in the following areas(to which we've never been):
-Italy: Rome, Florence, Milan, etc.
-Lisbon: We would enjoy staying here for a few nights.
-French Riviera

We're both relatively active people who love to walk and bike around beautiful cities during the summer. We're hoping to split our trip among 2 or 3 cities, with the potential to go out to the Mediterranean coast at some point as well. We each love food, although in different ways; we both love trying new food, but she is a picky eater(mostly vegetarian, as well) and I will eat almost anything. We like seeing some tourist attractions, but often find that we most enjoy exploring cities on our own. Finding a beautiful beach would be a great treat; in the past, she hiked part of the Iberian Coast and came across a beautiful secluded beach.

Budget-wise, we're looking at a moderate budget of about $1800-2000 per person, including daily food costs, etc. For this reason, much of Italy is out of the question, but Spain and Portugal may be good options. For flights, it looks like the best options from Boston are Lisbon, Madrid, Rome, and Milan, although we would be open to a multi-city flight(Boston->Lisbon->Madrid->Boston, for example).

Does anyone have any recommendations? Thank you very much for your help!

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