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Italy with Baby in December

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We are going to Italy with our 14 month old baby at the end of Dec, for 2 weeks. A few questions....

1) Is it too cold in Dec-Jan to walk around with a baby? We are going to be in Rome, Florence and the Amalfi Coast.

2) The eternal question -- stroller or backpack? or both? We are planning on using public transportation everywhere.

3) Any recommendations on baby-friendly hotels in Rome, Florence and Sorrento.

4) Any packing suggestions... regarding adult clothing as well as baby items. What kind of rain-gear should we bring with us?

Thanks much!

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