Itinerary review please!

Jill: This may be painful but I would save Rome for another trip, fly in & out of Milan and allocate your days as follows:

Milan - 2 nights
Venice - 3 nights
Florence - 4 nights
Tuscany - 3 nights
Cinque Terre - 2 or 3 nights

I assume you are driving and don't want to spend TOO much time in the car.

David
San Francisco

Oh for gawds sake David they cannot go to Italy for their first trip and NOT see Rome. RU driving or going by train to these other locales? Drop Milan. I'd also NOT pressure yourself into getting somewhere because you have a reservation Plan accordingly but give yourself time to explore especially if you are driving.
Beautiful country. Enjoy. Ciao.

Hi Jill,
Just got done doing my own first time to Italy itinerary and from what I can see, you've done a great job...pretty simular to my own. The only thing I would change, and this is my opinion from what I've read by other travelers, is to skip Milan and add on that extra day to CT. Milan is big city and I think your time is better spent in "true Italy". An extra day would also be great spent in Venice. My trip is only 13 days....wish I had those X days....Happy traveling! :)

Hi Jill, Could you flly into Rome and fly home from Venice. It would save you backtracking back to Rome? We did Rome first in September because it was my husband's first trip to Italy and with his love of history everyone told us we must do it. He love Rome as I knew he would. We used the trains and did CT and finished up in one of my favorite cities - Venice. Just a suggestion unless you are locked into flying roundtrip Rome.

I would suggest flying into Venice and home from Rome.Venice with 2 nights is a good place for Jet Lag,Much better then Rome.Train to Siena and stay 2 nights wirth the full day used to Bus to Florence,then train to the Cinque Terre.When leaving the CT, train to LaSpieza and rent a car for a few days in the hill towns(2-5 days)driving to Orvieto where you drop off the car and train to Rome.

I agree with Jack; arriving in Venice would be a good idea. Rome might be a bit overwhelming for first-time visitors to Italy on the first day, especially if you're arriving in the morning and want to do some sightseeing. Venice would be much more manageable since you can just wander on foot without having to worry about watching out for cars while in a jet-lagged haze! Just be prepared for it to be humid if you're travelling in July/August. If you're travelling in March, it can be quite cool.