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Italy June 2014, lodging and logistics

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3 days and 13 nights, arriving 7:30am June 15, Sunday, husband and I with 2 teenage boys (15 and 17)
Day 1-arrive in Rome, take car or train to Assisi-1 night
Day 2-daily Mass, enjoy area, leave by noon off to our base for 3 nights-Tuscany

Need some place to be our base but not sure where, considering agritourism, some will let us stay for 3 nights,
Things we want to see and do-visit one winery, taste olive oil, go to San Gimignano, hike, enjoy the views.

Day 5-leave and drive and drop off car before Cinque Terre, stop at Pisa and Lucca on the way

3 nights in Cinque Terre- if we have a car where do we drop it?

leave by train to Rome for 5 days, 6 nights
One day from Rome would be a long day trip to Pompei
Leave from Rome.

Little background, I have been to Europe and family hasn't. Kids and husband want Pompei, Hubby wants Tuscany, I want CT. Everyone is excited about 4 days in Rome. Kids love to eat, and try anything. Considering apartment in Rome. Would like to find lodging, no more than $200 a night, and I am worried about that. Need a place that is clean and safe, I don't need the bells and whistles. Staying at winery with olive trees in Tuscany would take care of my husband.

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