need itinerary planning help

Meredith, you are right to be worried about spending all your time in transit. If you are leaving on Saturday noon, you need to leave for the airport early morning, so you only have 6 days to see 4 places. Assume you will lose at least 1/2 day each time you change location, so you will be spending most of your time driving/on trains and dealing with lodging. Rome, Florence, or Venice could easily occupy your entire 6 days. But if you want to see more, I'd pick two places, and maybe do one day trip elsewhere. Orvieto is a nice day trip from Rome. Or you could stay in either Florence or Venice and visit the other as a day trip, if you really want to see both. If you haven't already purchased your plane tickets, consider flying into Rome and out of Florence or Venice. To get a realistic idea of transit times:
Check the Deutsche Bahn or Trenitalia website for the length of the train trips. And then add a meaningful chunk of extra time for checking out of your hotel, getting lost/finding the train station, buying tickets, finding your train, and finding your hotel in the new city.

Considering your tight timeframe, I would eliminate either Venice or the CT region.

I have not been to Italy but I just spend over a week (a couple of hours every day) planning my 2 week vacation (will be there in August). I am visiting Rome (4), Cinque Terre (2), Sienna (3), Florence (2) and Venice (2). My advice it based on the travel times I estimated (using train itineraries, etc.) I am not an expert but I hope this can be helpful. Bottom line you'll probably have to choose between: A) Rome - Cinque Terre - Florence - Rome B) Rome - Florence - Venice - Rome Cinque Terre is suppose to be beautiful but it would take the most in term of transit time. Imagine you were to visit all places an example of a itinerary would be (ET = Express Train and RT = Regional Train): 1. Rome to Cinque Terre (between 3.75 hrs. ET and 4.5 hrs. RT ) 2. Cinque Terre to Florence (about 2.5 hrs. ET) 3. Florence to Venice (2 hrs. ET )
4. Venice to Rome (2 hrs. ET) Basically given the transit times you will probably get the most out of doing itinerary B since although Venice it further north it is connected with Florence and Rome via express trains. So instead of going Rome - CT and CT - Florence you can just take a Rome to Florence train (about 1.5 hrs.). The benefit of itinerary A is that you could visit smaller in-between towns but that might not be a good idea since you'll want to get as many 'full days' as possible in each of the places. Please take into account days in which museums are close in the different cities you are visiting (e.g. Mondays for many museums, Sundays for Vatican, and Holidays like August 15). :)

You have lots of locations and probably not enough days to do everything. I do like whirlwind trips but this is a lot of traveling and not much time to enjoy. You could start in Rome and spend 2 days there to see everything you want, then take the train to Florence. From there you can take the train to CT, then on to Venice. From there take the train back to Rome and fly out... do not go back into the city itself. The other thing you might want to do is check with the airline about switching your flight to be out of Venice. Given the time you will lose and the expense of the train back to Rome, it might be worth the change fee. You will certainly gain some time.

Hello, Meredith. I used to live 4 miles from you. We visited Florence/Chianti, Venice and Rome a year ago, but took 2 weeks to do it. Rome itself is worth a 7 day trip, but you can do highlights in 3 days. Florence is also worth at least 4 days, but highlights can be done in 2 days. Venice is worth 3 days, but can be seen in 2 days. The Cinque Terre is out of the way, and should be saved for future visits. And your first and last days are spent going and coming from the airport. And every move takes 1/2 day. As far as your 7 days in Italy, it sounds as if there's nothing that can be done to grab 3-4 more days, or fly open jaw into Venice and out of Rome. That said, fly into Rome and take an immediate train to Venice. Spend 2 days then take a train down to Florence (149 miles) and spend 3 days. Take the train to Rome and spend the rest of your time there.
That's the best you can do.

We did Rome, Florence and Venice two years ago but had much longer time frame. We also had the dilemma of round trip from Rome. My daughter -in-law came up with the idea to take the train from Rome to Venice then back tracking to Florence and then back to Rome. That way we only had one long day of travel. I also recommend skipping CT for this visit.

I am sorry to pile on with the others, but you simply do not have enough time for all that you want to do. I have the same cities as you for a June trip, have set aside 15-days, am flying into Venice and out of Rome, and still feel rushed with the itinerary. I would do Rome, Florence, Venice, back to Rome for the flight (maybe the night train and then straight to the airport).
The suggestion of calling and having your flight changed is a good one. Price it against the train back to Rome (and time saved), and if it comes remotely close, then try and get that changed.

I like Cathy's plan. If you stay in Rome at the beginning and at the end, that also means one more hotel change. So I'd head straight for Venice from the airport, go to your hotel, at least to leave your luggage. If your room is ready, take a shower, change clothes, and go out for a walk, ride the vaporetto up and down the Grand Canal, and go to bed early, hopefully sleep through the night. Sat-Sun, sleep in Venice. Mon-Tues, sleep in Florence Wed-Fri, sleep in Rome. Go from Venice to Florence first thing in the morning on Monday, or at the end of the day (depending on where you want the extra day). The museums in Florence will be closed on Monday.
Travel to Rome on Wednesday evening.

With only 7 days and RT flights out of rome, you really don't have much time to go elsewhere. Why not save Florence, CT, and Venice for another trip? You can concentrate on Rome since there is a LOT to do and see there, plus you could take day trips to places like the Amalfi coast, Pompeii, Naples, Orvieto, etc.

Thanks to everyone for their input. We decided to do two days each in Rome, Florence and Cinque Terra. We will see Venice on our next trip.