Revised Itinerary: Milan, Venice, Tuscany, Rome help

After Venice, spend at least two nights in Florence and see the sites and enjoy Everything Florence has to offer, including the piazzas at night! On your way out, rent your car at the airport (or even better at the train station if possible) and return it there after your time in Tuscany. When you return the car in Florence, take one of the high speed trains to Rome. Train back to Milan for your flight back to the US.
Please let us all know how you like flying on Emerates! You can't beat the price, and I agree that I'd rather spend an extra four hours on a train than on an airplane!

You have enough time in Rome that you could take a day trip to Ostia Antica or even spend a night in Naples and enjoy Pompei. But there's never such thing as too much time exploring Rome, which is why I keep going back.

If you do a couple of nights in Florence, then I would take a day from Rome to add to Tuscany... there is always another hilltown or village or winery to visit. I like to pick up my car at the airport as I do not want to take a chance of al those high priced tickets. It is easy to just head out on the freeway and not worry about driving on the wrong roads. Returning is just as easy, or you could drive to another town closer to Rome and drop the car and train to Rome. You have a fair amount of time so I would give 2 nites to stay in Florence, then you don't have to bother doing a day trip or two back into the city. If you don't care about seeing Florence then you could get your car as you leave Venice and find a few places to stop along the way. You could then still do a day trip to Florence to see the highlights. I love just meandering around the hilltowns in Tuscany and taking any little turn on the road that looks interesting. Have plenty of food in your car for an impromptu picnic along the way. If it were my trip I would do less city and more countryside. I enjoyed Rome, but I can only take it for a few days... it is chaotic and crowded and intense, so I limit my time there.

Rather than juggle arrival with a train to Venice I would get a local train to Lake Como and 'acclimatize' to Italy.
Then you can book your onward trains with confidence because you will be on the ground.
Pick up and drop off your car in Florence or Siena.

Como (2)
Venice (3)
Florence (2)
Tuscany (3 or 4)
Rome (4 or 5)

Make sure you book a train from Rome to Milan (3 hr journey) no later that 8am to make your 4pm departure flight.

Thanks for the responses!

Djp_syd, how long does it take to get from Milan to Como, then Como to Venice? Would this add a lot of extra time travel time to our trip?

Looks like a great itinerary! Good thinking utilizing Milan for flights (I made the mistake of not). I'm really glad you are spending two full days in Venice - we almost only did only one full day and I would have definitely regretted it.

As others have said, I would really seriously consider spending dedicated time in Florence. I am somewhat of a foodie and I can say that the best food that I've had in my life was there. You could base yourself in Florence for 4 or so days - take 1-2 days of that time for day trips to the various hill towns. Everyone says it, and I didn't believe it at first, but the action of packing up and moving to a new location to sleep really is a drain.

One other comment. Taking a train from Rome to Milan on the day of your flight home is asking for trouble. I would maybe head back to Milan the night before and stay there for the night - maybe even see 1-2 Milan sites the morning of your flight - or get a return flight from Rome itself.

I agree with djp_syd. Better to deal with jetlag a the lower cost of a place near Lake Como then in the very expensive Venice. Lake Garda is another option.

We are following Rick Steve's 21 day tour and spent one night in Milan and then on to Lake Como. It was great to recover from jet lag and get our bearings in Varenna which is absolutely beautiful. We ate at the restaurants on the water there - one has a Rick Steve's guide book in the window and is very good but all the food was good.

People were friendly and helpful and we got used to Italian phrases etc.

I would skip using the ladies room at the Varenna if at all possible which is just a hole in the ground that requires good balance to use. No paper products of any kind either.

In Tuscany, Montepulciano is beautiful and enjoyable to explore on foot. If you try to depart Montepuliciano on Sunday, it becomes Hotel California - you can stay as long as you want, but never leave. The trains run, but the buses to the train station do not making is very difficult to get a taxi. and it is 8 kilometers to the train station

We are moving on to Orvieto today.

One additional note - I know that you plan to rent a car for Tuscany which I know many people do. I have noticed that parking is an extreme problem especially with so many tourists.

We are in Montepucliano and cars cannot be driven through portions of the city and I imagine other hill towns are the same way. Parking is an issue with huge fines.

We have opted to not rent a car and just enjoy exploring the village on foot - we have been here 3 nights and I am glad we are not dealing with a car. We see the countryside from buses and trains - but I know everyone feels differently about this.

Its an hour from Milan to Como on the train with departures usually every half hour, so not adding too much. Como to Venice is 3.25hrs with a change of train in Milan. It would give me peace of mind on arrival not stressing about making the onward journey.