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18 days in Italy with NO RESERVATIONS? Am I crazy?

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My wife and I (and our Shih-tzu) are planning an 18 day trip to Italy in June 2013. Done alot of research on traveling with our pet (and land travel). I've spoken to several people who have rented cars and they've all said it's not so bad, with the exception of navigating in the bigger cities. My wife would like to "jump in a car and go". We're planning on flying into Milan and then want to go to Reggio, Tuscany, Cinque Terra , Lake Como (where we spent 10 days, 8 years ago) and back to Milan to return home. Most interested in staying in countryside Inns, wineries or Villas (except Como; we're staying at the same hotel we stayed in before, in Bellagio) and taking day trips to the bigger cities (if we want to). Am I crazy to think that, at that time of year, we can just pull into a place and get a room. Our idea of a perfect vacation in Italy is seeing the countryside, rolling hills, wineries and small towns. That's the vision, but not sure if it's believable. We'd appreciate any insight, especially from anyone who has done this. Thanks

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