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Italy in October with 1 year old

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I am planning a trip to Italy for two weeks in October including a day each way for travel. I am trying to get the most time vacationing and less time traveling (2 transfers at most) since it will be our first time traveling internationally with our son. It is our first time in Italy but we have been to other places in Europe. Rome is a must for my husband and visiting a winery or two is a must for me. I am a fan of Barbera and just discovered this is in the Piedmont region and not Tuscany so now I am torn on which area to visit. I would alo like to see the coast if possible. Venice is on the list as well but I'm not sure how it fits due to distance from Rome.

My husband and I are most interested in seeng your typicsl sites like Colliseum, Vatican City, enjoying good food and wine, and experiencing the Italian way of life. I would really appreciate proposed itineraries and must sees as I am becoming increasingly frustrated with planning.

Thanks!

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