Ok Another try at this:

Rome 4 days (Maybe a day trip to Civita)
Rome to Seiena
Siena 2days
Siena to Florence
Florence 3 days (Day trip if possible doubt it)
Florence to Venice
Venice 4 days (day trip if possible)
Venice to Milan
Milan 2 days

In case anyone else is confused and/or curious, here is the website for Civita di Bagnoregio
http://www.civitadibagnoregio.it/
Apparently Rick Steves considers it the perfect Italian hill town

Wow. You are taking the advice of The_Pixies to bus between Siena and Assisi. Two towns The_Pixies has never visited ("We did not visit Assisi or Siena") and a bus that The_Pixies has never ridden ("I think it is faster and easier").

Stick a fork in me I'm done. Some people can't be helped.

First time posting: From reading your rough plans, even someone who's never been to Italy, yet traveled enough to other places would blanche at the thought of what are you are trying to accomplish. I am in my early 30s and pockets do not run deep.

Your posted here looking for advice as your name implies, yet you seem critical of what's being said. You offered little detail as to what your main plans are and just said, "I like all of it," so the responses you receive are going to be based on your vague list of wants. You post a crazy itinerary, yet state that you want to see a lot.

My suggestion:

1. Do some research as to why you want to see some of these places. Why Rome? Are you into ancient ruins? Are you into history? Art? Rather than just saying all of it, think about whether you could walk through the ruins and really be interested in the history behind it or if you would be the type to just walk through it and say, "Oh neat. Old stuff. Move along." When you figure out what you want to do, you might find yourself wanting to spend more time in one place and less in another. You don't need to split up each place evenly.

2. If you really want to see all of those places all in one go, then I say do it. You seem pretty set on selecting that many places, so why not? You could always go back and revisit, as you mentioned. 3 days in each place will give you an idea for the next time you return as far as if you want to return to a particular city or not.

3. Another alternative: If you plan on coming back to Italy, why not just choose maybe 2 places now and make a couple day trips then the next time you return, choose 2 other places. For an example, on the trip that I am planning, I am only selecting Rome and Florence and then doing a couple day trips from each of those places. Next time I return to Italy, I then plan on selecting Milan and Venice.

looking4advice- I think that's a workable plan (Rome, Siena, Florence, Venice, and Milan). One thing I really recommend while planning though is to think in terms of NIGHTS and not days.

Nights are concrete. "Days" are elastic depending on whether not they are arrival or departure days, or actual full rise and go to bed in the same place days. Sometimes planning things out in days can be deceiving and make it appear that you have more sightseeing time than you really do. It also helps me keep things straight when it comes time to make accommodation reservations.

<i>Rome 4 days (Maybe a day trip to Civita)
Rome to Siena
Siena 2days
Siena to Florence
Florence 3 days (Day trip if possible doubt it)
Florence to Venice
Venice 4 days (day trip if possible)
Venice to Milan
Milan 2 days</i>

10000% better. Not perfect - but few trips are. This is totally doable. Some of us would tweak here and there, but that is certainly a reasonable plan.

Thanks everyone for your input..

Actually kybourbon through my research that is recommended.

Thanks Janisj... Sorry about the above post. It is frustrating after a while..

We already have a B&B in Trastevere area in Rome booked. 75 Euro which from what I hear is not bad for this area.

We have also booked the www.ilsalottodifirenze.it in FLorence.

Does someone have recommendations for Venice or Milan?

Thank you

I have been reading this saga and I am exhausted already. YOur last set of ideas seems reasonable but remember you will lose the first day from jet lag and one of the days to fly home no matter when you plane leaves. The airport in Milan is further away from the city thn you imagine. I

Rome 4 days (Maybe a day trip to Civita) look back at what KY Bourbon says about the train. ASk yourself why is a must see town on this trip? If you do this you will losea full day that is already.

Rome to Siena Train is between 3.5 -4 hours depends on the train

Siena 2days
Siena to Florence train takes 1.5 hours

Florence 3 days Here I might add a day . (Day trip if possible doubt it) YOu can take many excursions from Florence- Check www.viator.com for ideas. There are many companies that offer day trips.

Florence to Venice train takes 2.5 + hours

Venice 4 days (day trip if possible)
Venice to Milan train 2.5 hours
Milan 2 days

Appres_Londree is right about how you shouldplan. Count nights. You hotels will want to know aobut number of nights.Do you have any reservations at all or are you going to have to find a place to sleep after you arrive? YOu can buy your museum tickets ahead, train tickets too.

Did anyone but me notice that at 7:19 they were still pretending to ask for advise and was still working on itinerary, then at 8:07 they said they had already made reservations in Rome and Florence.
HUH??
IMO, this poster is messing with us...

OK, a last reply. Please don't anyone else reply to this travel obsessive, with attention defecit problems, claiming to be looking 4 advice. Let it sink down the Europe/Italy list - I think that jetsetj hit the nail on the head.

We are flying into Rome so what is wrong with booking the room for those days. My wife and I agreed on the Florence dates so i booked that also. Really Do not see the big deal hear and I am not messing with anyone. We already had the places picked out just needed to cement the dates. Once that was done booking is easy with the internet these days. Thanks for everyones help.

The last itinerary looks pretty reasonable although still more than I would try to do. I think Apres_Londee's advice to think in terms of nights in each place is very good. It helps you to concentrate on how much time you have for sightseeing in each place before you move on to the next destination.

A couple of words on Italian trains: We had three 'major' train rides during our recent vacation. Two of those legs were delayed. The first one for 1.5 hours (Vernazza to Florence) and the second one for 4.5hours (Florence to Venice on the Eurostar). The third one (Pisa to Vernazza)was crowded to the point of claustrophobia but that might not be the case in September.

Just something to keep in mind when planning a tight schedule. Leave yourself some room to manuver, Italian trains don't run on a Swiss schedule.

I actually like your last itinerary and find it quite doable. I tend to travel faster than many on this board (although not nearly as fast as what your first couple of itineraries suggested), but it just depends on what kinds of things you like to do.

4 days in Rome is good. Obviously there is a lot to see and do; we've been three times and still have yet to visit the Sistine Chapel among other places.

I admit I don't understand some people's logic on losing the first day due to jet lag. I guess I'm fortunate but my husband and I have little problems with jetlag (mostly thanks to Ambien on the flight over) and our first day is never a wash. We usually arrive early enough to have time to get a feel for the city, maybe do some sightseeing, and have a nice dinner before heading to bed early. Still, you will probably want to take it easy since this will be your wife's first trip overseas and jetlag affects everyone differently.

Tracy

Thank you Tracy and Marigross for your advice.