Northern Italy

Steve, As this is your first visit to Italy, I'd suggest starting in the north and working south to Rome, especially as you might be travelling in September. This will hopefully provide the best weather for the trip and also the culture becomes more "intense" as you venture south. One city that's conspicuous by it's absence is Florence. Is there a reason you won't be stopping there? Siena would also be a good place to consider. However, you'll need to prioritize due to the short two week time frame. I'd suggest picking up a copy of the Italy 2011 Guidebook, as that will provide you with good information on each of the places you want to visit and others that you may not have considered, as well as transportation, sightseeing, restaurant and other information. Good luck with your planning!

I second Ken's recommendation to start north and go south. And do buy the RS Italy book. It contains really good descriptions of different regions and cities that you might enjoy seeing.

It all depends on your priorities, but to me it doesn't seem right to visit Italy and not spend some time in Tuscany! I had visited Italy about 8 times before I finally made it to Rome. I really didn't have a burning desire to see it above the other places I wanted to visit. I'm glad I've been now but I only choose my travel destinations based on my dream of that trip. So, I guess I would ask what is your dream of Italy and where will you find it? Vineyards, hilltop villages, Venice canals... So, I would not bother with Rome unless you really want to go there. There are so many other things to do that might be better for you.

I'd suggest spending 5 days in Rome (including a day trip to Orvieto), 3 days in Venice, 3 days in the Cinque Terre & 3 days in Siena &/or Florence. If you choose to stay in Siena then visit Florence as a day trip or vice versa. I agree with the others that your itinerary should include a little bit of Tuscany. Siena and Florence are easily accessed by public transportation so no need for a car. I also agree that if you go in September, you should start in the north and work your way south to Rome. I would definitely fly open jaw (into Venice or Milan & out of Rome).

You might consider doing a little side trip from Rome to Ostia Antica to see the ruins. It's not as impressive as Pompei, but since you aren't going to Pompei, it would be interesting. Ostia Antica is very easy to get to on public transit from Rome. You could do this trip easily in half a day. I agree with previous posts: start in the North and work your way down to Rome. If you are thinking of starting in Milan and skipping Venice, then I would suggest taking a one hour train ride north of Milan to visit Varenna on Lake Como. Stay there 2 nights. While you are there, you can take the public ferry for a 15 minute ride to Bellagio and spend a few hours visiting. However, I would recommend seeing Venice instead. I'm just suggesting this in case you don't want to see Venice (can't imagine anyone not wanting to!)

Thank you all so much for the input, and please keep it coming. I didn't even consider traveling North to South, but it sounds like the consensus from those with the experience. We haven't ruled out Florence/Tuscany, we just wanted to get some feedback from this forum before we started adding more destinations to our itinerary. Thanks again.

Having been recently planning my upcoming 3 week trip to Italy and visiting many of the same areas you should look on a map and also look at the train schedules. http://orario.trenitalia.com/ We are doing Venice/Florence/Siena/Cinque Terre/Rome. You could do Venice/Milan/CT/Rome but what about Tuscany? If you do choose Tuscany then that changes it all. I decided to save Milan for my next trip to Italy, I can't do it all and I plan to go back. I've notices flights to Milan are often the least expensive but do book open Jaw with either Milan or Venice on one end and Rome on the other. Probably at least 3 nights per city more is you have excursions planned or have particular interests. Train travel between the locations you have chosen are 3.5-5 hours depending on the train.
Happy planning!

Don't feel like you "must" visit Rome on your first visit Italy. Plan that you'll return; maybe you could visit place in the north on this visit, and then Rome, Pompeii, the Amalfi coast, etc. on your NEXT trip. You haven't said much about what you're interested in. Do you love Renaissance art? Then you should probably include several days in Florence. Love the idea of a city built on water, plus some great art as well? More days in Venice. Have you always wanted to see the Last Supper, in Milan, then include at least one night there. Do you love the countryside and hiking? More time in the Cinque Terre! Answers to questions like this will determine how many days, if any, to spend in Venice, Milan, Florence, the Cinque Terre, etc. And, of course, if you love everything about ancient Rome, then spend the bulk of your time in Rome! IMHO, Tuscany is best experienced with a rental car, to be able to drive along the scenic, winding roads from village to village. It can be done by public transportation, but not as easily. But if you decide you'd like to visit a smaller city, then include Siena or Orvieto in your itinerary.

Thanks again for the input, especially the ideas on day trips. Ruins are a great interest so we'll definitely research Ostia Antica.

When we visited Italy for the first time in 2008 we flew the redeye from US landing in Milan in the morning. We then visited the Duomo and saw The Last Supper in the afternoon (after making reservations ahead of time) and then took the train per Rick's instructions and spent 2 nights in Varenna on Lake Como. The relaxing day on Lake Como was a great way to adjust to the jet lag. We then took the train back to Milan and on to Venice and joined a 10 day Rick Steves Venice, Florence, and Rome tour + 2 extra days on our own in Rome before flying out of Rome. The 15 day trip (including travel days) was very doable for us and great intro to the wonderful country of Italy.