Italy travel plan suggestion for two weeks

Although I love Sicily, I have to agree with Steve that you should cut it from your itinerary. It's too far. I also recommend cutting Naples and Milan. I've been to Italy ten times, and Naples is the only place I couldn't wait to leave. It's dirty and unbelievably disorganized. Milan just isn't up there with the big three. You could allow three days for Venice, including a daytrip to the lagoon islands, Padova, or Verona. Four or five days would be good for Florence and some of the nearby Tuscan towns; and the remaining time for Rome with a daytrip to Orvieto. You should look into the possibility of staying in an agriturismo for part of your trip. It's a uniquely Italian experience. Many of them have pools and play equipment, which your child will appreciate. They give you a bit of a break from art museums and historic sights, while providing an insight into Italian culture. Lots of agriturismi in Tuscany, and I know a wonderful b&b an hour from Rome if you have a car. PM if interested.

Too much for 2 weeks, IMHO. You have 6 destinations you "definitely" want to cover, so that's 2 or 3 days in each. Which is really less because of travel time between destinations. To say nothing of the fact that Sicily is an entire island, not a city. But if you want to return from your trip and be able to say you've been in all those places and even seen a few things, you can do that in 2 weeks.

You can find info on budgets, prices for recommende hotels & restaurants, misc. fees, and how long to stay in various places in a handy tool called the "guidebook". RS writes some, as do several other companies. If you're looking for someone else to do much of the legwork for you then you could try a travel agent, or the paid trip consulting RS offers at http://www.ricksteves.com/about/consulting.htm

Yes, airfare is considerably cheaper flying a week earlier.

I notice you say you have two weeks. Not really though -- if the 28th is a flyout day and the 9th is your return, you'll have 10 days on the ground.

HSR,

With such a short time frame, I'd suggest focusing on Rome and north this trip and cover Naples and Sicily on a future trip. Planning to visit 6 locations within 14 days is a bit "ambitious", to say the least, and doesn't allow for travel times. That only provides about 2.3 days in each city. Getting to and from Sicily especially will require significant travel time (even with budget flights, each way will take at least half a day).

Another thing to keep in mind is that you'll lose the first day in flight times and time zone changes and the last day will be spent on the trip home, so you'll only have 12 days for touring.

Under the same circumstances, I'd structure somewhat like this:

Day 1: Flight to Venice / Rome

Day 2: Arrive (recover from jet lag will take a day or two - check the Guidebooks for options on getting from the airport to Venice).

Day 3,4: Venice

Day 5,6: Milan (trip from Venice is only a few hours by train - be sure to watch your belongings carefully in Milano Centrale).

Day 7-9: Florence (trip from Milan is only a few hours). You could take day trips to Siena, Pisa or other nearby locations while in Florence - if you're considering day trips, you might drop one day from Milan and add to Florence.

Day 10-13: Rome (there's a LOT to see and do in Rome, so it's worthwhile to allocate more time - again, watch your belongings carefully in Roma Termini, on the Metro and especially on the #64 Bus, should you happen to use that - wear a Money Belt!).

Day 14: Flight home

If this is your first trip to Europe, Europe Through The Back Door will provide lots of information on how to travel "well" in Europe (especially the chapter on "rail skills"). The Italy 2010 Guidebook has lots of great information on Hotels, restaurants, Museum costs and hours, etc. and tips on things like avoiding queues. I find the Italy book is a good resource to pack along on the trip.

Happy travels!

I like Ken's post, but with 12 days available, I'd cut Milan and add a day to each Florence and Rome.

Given 12 days, I'd probably spend them similar to Ken's list, but with some modifications (I'm not a Venice fan, but am a big antiquities fan).
1-3 Rome, Outdoors on day 1, Day 2 side-trip Pompeii, Day 3 Vatican.
4-5 morning train to Venice, 1 night Venice, afternoon train to Florence, Night florence.
6-9 Florence, possible stop in countryside on way back to Rome
10-12 Rome, side trips to Ostia Antica

For a budget... traveling 2 adults with 1 child in Italy... traveling semi-close to the ground, but able to grab a taxi if you're tired, get a little nicer room... I'd plan ~120E per adult per day plus 50E to accomodate the child, or 290E per day, which at today's exchange rate is a scary $408.90 per day. You should be able to do better than this, but I'd be prepared to spend $4,500 to $5,000 plus Airfare.