Hello everyone! My husband and I are in the preliminary planning stages for our vacation to Italy September 2015. We're thinking of staying 2 weeks- 2 1/2 weeks. I was hoping to get some advice on how long to stay at each of the locations, as well as if you think there are any other places/attractions we shouldn't miss.

Stops:
Florence: For the art, mostly.
Cinque Terra: I've heard great things, and we would be planning on staying in one of the villages and hiking the (blue?) trail.
Rome: The Vatican, The Colosseum etc.

My husband also talked about the possibility of going to Milan- he has some Italian friends at work and they recommend it.

Any advice for someone who is relatively new to Europe travel (I did study abroad in college, but that was pretty well planned out for me) would be appreciated.

Thanks!

I think the best advice is to read through old itinerary posts and trip reports to find someone whose travel style meshes with yours, and then sort of base your trip on those. You have avoided the most common mistake--trying to squeeze too much in, so you are off to a great start. The next step would be to search for open jaw flights, or plan a good route if open jaw does not work out.

Assume 3-4 nights in any location (except perhaps CT) plus 1 day to move between them and in 15 days, you'll see 3-4 places. The 'big three' tend to be Florence, Rome and Venice. You may want to consider:
Fly into Milan, get over your jet lag, see the Last Supper, LaScala, and Duomo; rent a car and take a day trip to the villages and wineries of the piedmont region -
Take a train or drive to Florence; we had three days there and need to return for more: duomo, pitti place, accademia gallery, uffizi gallery, etc
Take and train or drive to Rome via Tuscany. Stop for a day in Sienna, stay overnight at an agritoursimo as you'll be there during harvest season; see the abbey at San Antimo, tour the wineries
Drive on to Rome, see the sites and fly home from Rome

There is so much to see and do so plan your time carefully and hit the places that really interest you. Food and wine are excellent everywhere; art and history surround you. Milan does get a pass for many - we took an extra 2 days there and really enjoyed it rather than just driving thru enroute from Como to Verona. As our son said, "you'd be that close and NOT see the Last Supper???!!!"

Were it me, I would fly into Rome and jump right into all the excitement of being in Italy and the layer upon layer of history, then after some days, travel up to Florence by fast train (90 minutes) to do the art tour you want. Then take a train to le Cinque Terre and just kick back and enjoy a mini-vacation doing whatever you like for as long as you like, no real plans, and finish up by taking a train to Milan. I've generally enjoyed having Milan at the end of my trips because there a comes a moment after many days in Italy that getting to walk on a straight sidewalk feels like a special treat. And Milan can make a nice halfway-house between leaving all the antiquity of Italy and returning to that other world of shopping malls, glass office buildings and clocks. I would budget enough time in Milan to go have lunch at Lago di Como if the weather is nice. If you have the dough, you could even spend your last evening in Italy on the lake and get a driver to take you to Milan airport in time for your flight the next morning (usually costs 100e plus).

Rome - 5 to 7 days, not counting arrival day. With 7 days, you could spend time outside the city exploring the ruins of Ostia Antica with a stop at St. Paul Outside the Walls, one of the major basilicas. And/or visit Tivoli.

Florence - 5 - 6 days with a day trip to Siena.

Cinque Terre - 1.5 days.

Travel between locations is extra.

Venice would be a don't miss for me but it's difficult to visit both Venice and Cinque Terre as the train time between them is 6.5 to 7 hours.

Milan is a big business city in my opinion except for seeing the last Supper and walking the roof of the duomo. The one thing I like about it is that is close to the lakes which are lovely and a great Italian experience. Do you have to fly in and out of same city? if not then fly out of Rome and see the sights between Milan and Rome including Florence, Siena, Luca . Overnight in CT might not be enough if you plan on any relaxing or hiking. I would save Venice for another trip as it is quite a ways to go even on the train which is very efficient.

Rome & Florence are easily my favorites. Milan ,IMHO, is not worth the detour/time. We generally split our time between Tuscany, Rome & Florence. We've done Venice a few times, but we tend to enjoy other areas more. We also will be in Italy this September. I will be planning a get together (GTG) with Fodorites and Slow Travel forum members.
I recommend also the trip reports at Slow Travel to get a feel of different itineraries.
Agree with Adrienne about more time in Rome.

Rome, Florence, Venice--in decreasing order of time spent in each, with three nites in Venice.

Cinque Terre are not worth your time in a short trip, IMHO.