Itinerary Thoughts

Have you purchased plane tickets yet? Just need to know where your flight back to the USA originates on Day 13. Do you have any particular interest in Milan? If not, I would suggest heading straight to Venice from Milan and spend 2 nights in Venice. You can then take the train to Florence and proceed from there. The itinerary below assumes that you fly home from Rome.

1 Flight to Milan
2 AM Arrival - train to Venice
3 Venice
4 Venice to Florence (afternoon or early evening to maximize time in Venice for the day)
5 Florence
6 Day trip to Cinque Terre/sleep Florence
7 Florence to Sorrento
8 Sorrento/Pompeii/Positano
9 Capri/Sorrento/Salerno
10 Train to Rome
11 Rome (maybe a day trip to Orvieto)
12 Rome
13 Flight to USA

I hate to say it but I'd cut at least 1-2 cities from your list (perhaps Venice could be one since it is not your favorite?) A trip to Italy can most certainly be enjoyable without seeing the "big cities". How do you feel about an itenerary that is largely along the coast and in Tuscany?

1 Flight to Milan
2 AM Arrival, Milan - Take train to Cinque Terre
3 Cinque Terre
4 Cinque Terre
5 to Florence
6 Florence
7 Florence Day trip to Assisi
8 to Rome
9 Rome
10 Rome
11 Sorrento (see Pompeii)
12 Sorrento (see Capri)
13 Flight to USA

Are you able to find a flight from your city out of Naples airport? Or are you planning to fly home from Rome? I'd recommend making sure you are in Rome the night before your flight to avoid any scheduling issues. You wouldn't want to feel stressed or miss your flight home!

You might consider this alternative for the final week if your flying home from Rome:

8 Florence to Sorrento
9 Sorrento (see Pompeii)
10 Sorrento (see Capri)
11 to Rome
12 Rome
13 Fly Home

I'd go straight to Florence on landing. There's no point in staying in Milan. I'd also drop Venice since you aren't keen on it. There are so many great places in Italy, you'll enjoy wherever you do go, and the rest will be waiting for next time.

The CT is too far to do as a day trip. After Florence go there for at least one night, then on to Rome. The train connections are better that way. From Rome day-trip to Assisi (though it's better as an overnight).

Where are you flying home from? You should plan to spend your last night in your departure city.

I'd suggest dropping Milan, flying into Venice instead. Concentrate on the Amalfi Coast, with its diverse sights, instead of Cinque Terre.
1 Flight to Venice
2 Arrive Venice (2)
3 Venice
4 Venice to Florence (2)
5 Florence
6 Florence to Assisi (1)
7 Assisi to Rome (3)
8 Rome
9 Rome
10 Rome to Sorrento (3) via Naples
11 Day trip to Capri
12 Day trip to Pompeii
13 Flight to USA

Capri is too far to do as a day trip from Rome. By the time you get there it will be time to turn around and head back.

You have 9 full days. Your itinerary is too packed to be enjoyable. I would cut out some stops. If you didn't love Venice that would be one that I would cut. You can always come back to Italy and visit Venice. You want to visit the CT and your husband want to visit Assisi so those two should stay. I would add one other city and spend the time visiting those three. That will give you about 2.5 days in each before flying home.

You don't mention which airport you fly home from but be sure to be in that city the night before the flight.

Donna

Thank you all for the info! We have not yet bought our flights yet, but we're planning on flying in of Milan/Florence/Venice and out of Rome, so we don't have to back track.

Given that I've been to Capri does anyone have any thoughts on going to Cinque Terre over Capri? If we did go to CT, would we need to rent a car?

Are there any other places noticeably missing? We could probably add another day or two.

Thanks!

Since you have already been to Capri, and really want to go to Cinque Terre, go there! And I would spend 2 nights, gives you time to explore all the villages and hike (if you wish).

You don't need a car, it is very easily accessible by train. Each village is only a few minutes away from each other. There also is a ferry boat that runs between the villages, weather permitting. You can't drive in the villages, and trying to find parking outside is a hassle.

If you have a couple of extra days then you have no trouble doing both Cinque Terre and the Amalfi Coast.
However, like others, I would caution against so much moving about. It will start to detract from your enjoyment.
You could spend a night in Verona and Siena, or an extra night in Florence perhaps.

I agree that you will enjoy the trip more if you aren't changing hotels every other day. Try this on for size:

1 Flight to Milan
2 arrive Venice AM (2 nights), relax and soak up the atmosphere, ride the vaporetto up and down the Grand Canal, wander around the small canals
3 Venice - visit the main sights, take the vaporetto to Burano, it's a lovely ride across the lagoon
4 Early train to Florence (2 nights)
5 Florence
6 train to CT (2 nights)
7 CT
8 train to Rome (5 nights), including day trip to Pompeii and day trip to Assisi.

Hey, to me your itinerary seems a little tightly scheduled. You say this is your 2nd trip to Italy, you can always take a 3rd one to visit the other parts of the country. Don't just be tourist, explore the places; you will love it that way. Drop at least one place form your itinerary and you will get the time to roam around the other places on foot. If you are confused where to go and how to plan your trip, take a look at this Italy trip planner at http://www.triphobo.com/italy-europe, you can create your own itinerary and or can even edit an existing one you like. Regarding Venice, I think you should go there, never know with your husband by your side, it may feel a little different.