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boot of italy

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Im planning a 3 month trip to italy from the end of January 2017 (know it is winter) thought i would stay in Rome on arrival for 4 days then head down to the Boot of Italy by train Puglia,Lecce,Bari and what ever other towns that i think are nice. My only concern is that it will be cold and will these towns have enough for me to do? I have been coming to Italy for the past 10 years and have never been to this region and i just like to enjoy the food and the people in each place. After i have spent time in this area will return to Rome and head up to Ravenna, Ferrara, and then Bologna and go across to Siena, Lucca and stay a week or 2 in Florence. What do you think?

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