5 nights/Siena and 5 nights/Florence is this too much time?

5 nights in both of those cities is way too much. Unless you have some pressing desire to spend lots of time in Milan I would also axe those 2 nights. Spend some of those extra nights down south on the Amalfi Coast somewhere...

Kathy, My first suggestion would be to put all your Rome days together. This would eliminate a travel day. Consider landing in Rome and training to Florence, only about 1.5 hours from Rome, then Venice, Milan, Cinque Terre, Siena, Rome. Staying in Florence and Siena for five days each while doing daytrips is not too long, there is much to see in the area.
Another option would be to get a car to see some of Tuscany. This will give you some ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I would add more nights to Venice. We stayed 4 and wish we'd had 5. Plan time to wander, don't overschedule yourself, but take a full day to see the Laguna Islands, Murano, Burano and Torcello. I could never tire of just walking in Venice or Rome! IMHO 5 nights in Siena is a lot if you do not have a car. There is not that much to see and do in Siena itself. You can take bus tours to other hilltowns like Volterra, San Gimignano, Montalcino, etc. You can also take some escorted day tours to wineries and such. I have not been to Florence in many years, but it is very art and museum focused, so bear that in mind. You can of course day trip out of either city. Milan has only a few sites of major interest and they can be done in a day. If you do not have Last Supper reservations, I would not spend time there. Just my opinion. (But the Last Supper is worth seeing!) You are doing a lot of "big cities" with this itinerary. Some people may find that too intense, and you miss the small-town Italy culture and peace. Many people like Verona on the way to Venice. Orvieto is an often overlooked gem. Why not take 2 or 3 nights there? The town is worth a full day, and you can take a bus to Civita for a day trip. So all that said, I'd suggest this plan which sort of alternates big cities and smaller towns: - Rome 5 nights (since you are going back at the end) - CT 3 nights - Milan 2 nights (Last Supper reservation dependent, otherwise add these nights to places that interest you most) - Verona 2 nights - Venice 5 nights - Siena OR Florence 4 or 5 nights (not both) - Orvieto 2 or 3 nights - Rome 2 nights
This will give you a great taste of Italy from North to Rome.

5 nights in Florence AND 5 more nights in Siena would be longer than the typical traveler posting here spends. Typical for people posting here seems to be 3 to 4 days in either Florence or Siena. Of course, there's absolutely no reason why you have to do what the "typical" traveler here does, but I thought it might be useful to you as just another itinerary planning benchmark. As Henry says, 5 nights in Florence and 5 nights in Siena would suit some travelers, especially those with longer trips or who have been to Italy before and already done the basic Italy itinerary. I'm assuming this is a first trip to Florence and Siena. Some sleep in Florence the whole time and do Siena as a day trip from Florence, usually by bus (more convenient than the train). Some reverse it and sleep in Siena and do Florence as a day trip, although the problem with that is one day in Florence is not sufficient for some/many. Neither Florence nor Siena is particularly car-friendly. And this presents another planning challenge, because many want to explore Tuscany hill towns while sleeping in Florence or Siena, which brings up the problem of managing overnight parking and avoidance of ZTL's while sleeping in Florence or Siena. Some pick up the rental car on the last morning in Florence or Siena, on their way out of town. No one seems to have come up with the perfect way to do Florence, Siena, and the Tuscany hill towns. Everyone ends up making a decision, but none of the choices seem perfect, all involve tradeoffs.

Kathy, Are you doing Rome twice because you fly in-and-out of Rome? That was my assumption in offering advice. I hate one night stays so I would do two nights at the end if you are flying out of there. Gives you a day to see items on your list you may have missed in the first week. I left Rome after 5 nights with a huge list of "go back to" places and activities we missed! Laurel

Our thoughts for staying in Florence and Siena 5 days each is this: We want to attend Palio August 16 so a few days before to insure getting a place to stay and being there for all the excitement prior to Palio. Plus a day or two of touring the surrounding area by bus/train or tour guide. From Florence we thought we would do 2-3 days touring Florence and then a day trip to Pisa and Lucca in the same day. Is that feasible or should we give Lucca one day in itself. Any thoughts?

In 2009 we spent 5 nights in Siena, 5 in Florence and 7 in Rome. From Siena we took a day trip to San Gimignano. We thought we could have done with 4 nights but since you're going to see the Palio, 5 nights seems right. We had planned to do a day trip from Florence but there was so much to see and do that we decided just to get to know Florence. We could have used an extra day there. So to answer your question, the number of days each of us spends in a town depends on how we want to travel and what we want to do. But it seems that you probably picked a good number of nights for Siena and Florence.

I assume the Palio is like Mardi Gras, in that; there are a minimum number of days for hotels. And reservations and confirming payment made well in advance? Do the hotels require 5 days? If my memory serves me correct and my understanding of it correct. The Palio is the race around the Piazza. And there are a number of lead in events. Sounds like a lot of fun.

I just spent 2 days in Siena. I arrived around 1pm. Saw what I needed to see in that day. The next day, saw sights in the morning and then took a guided tour thru Chianti country and San Gimignano. I saw nearly all the sites listed in RS book in those 2 half days I had in Siena. I did not feel rushed, exhausted, or crazed. And being there I said to myself, I am glad I did not rent a car. I did not look like any fun. I also spent 3 days in Florence. I felt I gave Florence a good run over. I saw what I wanted to see, and once again, did not feel rushed. But I did not side trip. I wanted to do San Gim on my 3rd day but felt I could not leave Florence. So 5 days in florence for side trips might be ok.

With regards to spending some time in Siena around the Palio - I agree that 5 days would be good to see the both the city and its monuments as well as enjoy all the events connected to the Palio. I don't think there usually are minimum amount of nights required but definitely make your reservations ahead of time as the town gets packed. If you want to see the race, you have to consider getting tickets for the bleachers that are set up around the piazza del campo (expensive). Otherwise you have to try to get into the center of the piazza early on (free standing room) but from here you really don't see much but you do get to experience the atmosphere. We were in Siena a few days before the July race and saw the square being covered and packed with dirt in preparation for the race. There were nightly "contrada" or neighborhood dinners in the street during that week. My understanding is that some of these are open to the public but some are strictly for the neighborhood. There was marching and drumming throughout the day as well, it was an interesting experience overall even if we weren't there for the race itself. The city is completely transformed. Personally, I really like Siena. It is very different from Florence, they have very different "characters", if cities can have that. These two cities were enemies for centuries.

I think 5 days in Florence is great; you would be busy for all of those days without even taking a daytrip somewhere. I lived there for 2 weeks, took 4 daytrips, and still haven't seen everything I want to see in that city. If you aren't sure about the amount of time there, make a list of everything you want to see in Florence and a separate list of towns you'd like to take a daytrip to from Florence, and see how everything adds up.

Like Sarah, I was in Florence for 2 weeks and felt that I still didn't see everything I wanted to see. Whether 5 nights is too much depends on your interests and travel habits. The nice thing about having a 'home' base is that you don't need to schlep your luggage to a new lodging every couple of days! If you're in Siena during palio time, the city will be packed and you might have to stand in line to get into the main sights, so sightseeing will take a longer time. You could take daytrips out of Florence or Siena, visit vineyards on wine tours or take walks. (I'd recommend Walk About Tuscany for guided walks.) You can daytrip to Pisa, Lucca, Greve in Chianti, Arezzo, Volterra, San Gimignano, Montepulciano, poke around other hill towns. I've never rented a car in Tuscany and managed to get to places with buses and trains, but must admit that a car offers flexibility and freedom - bus schedules are usually tailored to suit local school schedules. Milan isn't a touristy city but it's an interesting contrast to Venice, Florence and Rome, with good (expensive) shopping and nightlife. I saw on the news page here that a new Museum of 20th century art (Museo del Novecento) just opened in Milan so that's something more to see! From Milan, you can also visit Lake Como, or Pavia with its famous monastery - a sight I've yet to see.