Italy Itinerary

I'm assuming that there's a valid reason for starting north working, south, then going back to the north to catch a flight. One night's enough in Bologna. You'll need two in Milan. You've short-changed Rome and over-killed Venice, swap a day between them. If you're short time somewhere else, rob it from the CT (or even skip it) since it doesn't rank anywhere close to the other places - - rest when you get home.

i would just do one night in Bologna between Venice and Florence...i did that when i went and it was just enough to take in the sights and eat the best food in italy. i would skip the CT...it is going to be a VERY long trip to/from there based on the other places you're going. i went from Siena to the CT to Rome, and i didn't think it was worth the trouble. i was also there in September/October, which is apparently the rainy season, and it rained the whole time i was in CT, so you should consider that. i'd add a night in Siena after Florence and maybe another night in Milan or Rome. i decided to skip Naples when i went as i heard it wasn't that nice...maybe you could stay in Rome instead and just do a long day trip to Pompeii/Naples? that would also make your trip back up to Milan shorter.

Is there any chance you can change your flight home to Rome or Naples to avoid the back-tracking? Unless you have your heart set on seeing the Last Supper, I'd skip Milan and add that night to Rome. Staying at least 2 nights in even a small town is preferable so that you have one full day. One night stays really don't allow much time ot touring and enjoying: you have an arrival day (check-in often 3:00PM) and a departure day (when you'll usually be out by 8:00 or 9:00 to catch your train to the next stop). Rome, Venice, Naples Region deserve more time. I think 3 nights is OK for Venice (you'll wish you had more but then you can go back another time), and ditto for Naples area. Rome should have at least 4 nights. Cut one location if you must (I agree with Ed that you could skip the CT; It's a lot of travel time to/from for such a short stay). What time of year are you going? A good way to determine how many nights you need in a place is to list out the sights you want to see, how long they will take, days & hours open, and see what kind of time it takes. RIck Steves has great planning guides for Rome & Venice on this site. Click on "Plan Your Trip" then on "Italy." As to Naples: Most people on this Helpline would recommend staying in Sorrento as a more peaceful place, access to the sea, etc. You can easily travel to Naples and Pompeii on the Circumvesuviana. If you indeed must fly out of Milan, spend only one night. We had a Milan departure, traveled there from Rome the day before, arriving about Noon. Saw the Duomo, shopped, 6:00 PM reservation for the Last Supper, had dinner, caught our flight the next day. Not worth two nights on your first trip.

I think too many Americans blow off Milan as a place with a painting, a church, and a spiffy shopping mall. It's also the largest commercial and industrial area in the country, has a couple or three dozen universities, a fairly well-known opera house, the di Brera art museum, the Sforza Castle which houses da Vinci's Codex, and a rather good archaeological museum. If you poke around a little, you can finds roman and celtic remnants. A week might be enough to give it a pretty good lick. It ain't all that shabby. It also has grub without the damn tomatoes.

Thanks Everyone, Unfortunately, I cannot fly out of Naples. I am using airline miles to pay for my trip and they don't allow flights on their partner airlines, which would be required to fly from Naples. I agree with spending more time in Florence and Rome and was wondering if I should cut Bologna. I think longer stays in fewer places is a much better plan. All that moving around is too exhausting and leaves little time for relaxation! Any ideas?

I would cut Bologna. I was in Bologna recently for a day on a similar (but shorter trip) and, with hindsight, wish I had left it out and added a day to the 1 day I had in Florence.

I did a trip like yours but in reverse. What was in the middle is different but you will see my point/advice here shortly. We flew into Milan and out of Venice. It was the only way my trip would have been affordable; Fly out of Venice $628, Fly out of Rome $950. We did Milan (1 night), Florence (3), Siena (2), Assisi (2), Rome (4), Venice (3). So how about this Venice->Rome->CT->Florence->Bologna->Milan. Or something like that, I don't have a map with me so I can't see if some of the cities in the middle need to be switched around. The trip from Venice to Rome is only about 2 hours so it isn't too much of a travel time waster. Start in the North, dip down south and make your way back up north.
I would then consider to take a day trip from Rome to do Pompeii. Take the nights away from Naples and add them to Venice, Florence, and Rome. But I have not interests in that part of Italy so I was not dying to go there and wanted to spend time in other regions. That drag from Naples back up to Milan when you are exhausted from your 18 day adventure could be a drag and cause you to take Milan for granted. We had 1 full day there and saw everything I wanted to see in that full day: Supper, Brera Art Gallery, Duomo, The Mall, and a walk thru the ritzy shop area. By time you get there from Naples, you may not want to do anything but organize your suitcase/bag for your flight home. Good luck with planning.

CK Not sure I read if this is your first trip to Italy or not. From your itineray it looks like it. Very very hard to make choices. I like Laurel's suggestions regarding your itinerary. I also suggest you drop at least one destination. The outliers in terms of difficulty to get there or time to get there are CT and Bologne or Naples. Also consider taking a discount airline from Naples to Milan on the same day as your flight if the timing works out. If you stay in Sorrento instead of Naples, there is a bus to the Naples Airport. I did not like Milan. Does not compare to any of the other Italian cities in my opinion. Unfortunately, heavy bombing during WWII and the post war buildings did nothing for the architecture of the city. Itineraries are always a work in progress. Keep us posted! Bobbie