Itinerary for Italy Oct 1 to 15
 

We are first timers in Italy, flying in & out of Milan. We hope to visit key cities like Rome, Venice, Florence and also catch a little of Tuscany. Appreciate any suggestions as we are unsure the weather and if train travel will permit us to cover most sights in this cities.

Five destinations in 14/15 days. Weather and train schedules won't be problems, but you might have trouble covering "most sights" in these cities. I suggest you figure out exactly what you want to see (and on what days since not everything is open every day) and then decide how much time you'll need in each place. You may need to drop one destination, but that city would have to be your choice.

Check train schedules here:

http://www.ferroviedellostato.it/homepage_en.html

You can't search October schedules yet. Just search days of the week you're considering for dates in the April/May. Timetables between these major cities don't change much during the year.

Many other people I know, that spent 15 days in Italy on a similar itinerary.
I think it is OK.
Milan: is a business and modern big city, important for fashion (nice but expensive shops). There is the Cenacolo of Leonardo, the Brera collection, but you have not so long time to spend, and I suggest you to stay here a short time. Venice's visit requires, at least, 3 days of your journey. you can spend another 3 days in Florence. You can do the trip from Florence to Rome, in 2/3 days spending time, on the way, for some famous hilly towns and the best italian countryside.
The rest of the days in Rome.
It sounds good.

I would agree with Jean - that is a lot of ground to cover in two weeks. I would highly suggest fitting in time for a drive through Tuscany, especially during that time of year. Siena is an absolute must-see. In my opinion, I also think Pisa is worth a stop. The Leaning Tower is the obvious notable attraction, but we really enjoyed the atmosphere of the town of Pisa itself. After seeing Milan, perhaps a train to Florence. After that, you could drive from Florence to Rome going through Tuscany (Siena, etc.), then train from Rome to Venice, and then back to Milan for your flight. No matter how you decide, enjoy your trip!!

For me, that would be a little too busy, but that's just MHO.

Consider that you're going to be in travel status 5 times, and each time is going to take about a half-day, by the time you get to the train station, take the train, and then get from the station to your hotel, etc. That means you're using 2-3 days to get from Point A to Point B. That limits your sightseeing to about 10 days.

So here's what I'd do, with approximate times.

One day in Milan. Train to Venice.

Three full days in Venice. Train to Florence.

Three full days in Florence. Add a day or use one of the three days to take a guided tour of Tuscany (I recommend Luca at hillsandroads.com) or take the bus to Siena for a day. Train to Rome.

Three full days in Rome. Train to Milan.

It would be better if you were flying into Milan and out of Rome, but I assume your flight arrangements have already been made.

Being the first time in Italy from Milan I would take a train to Venice. Stay in Venice 2 days and then take a train to Florence. Visit Florence within 2 days and then I would take a tour in Tuscany to visit nice towns like San Gimignano, Siena, Montalcino and the wine area of Chianti (Gaiole, Radda). I can suggest to contact a company we used in the past who are specialized for this kind of tour(www.drivearounditaly.com). Then from Florence, go to Rome by train and spend 3 days here. From Rome the best way is to get a fly back to Milan. Enjoy your trip!!

Jean: yes - I think we were being too ambitious as we forgot to consider the commuting time from point A to B, hunting for our hotels, etc. Thanks for the great reminder.
kleiserinc: is car rental expensive? the idea of driving from Florence to Rome via Tuscany sounds great.
k9korps: love your suggestion. Milan's not a must see for us, so we don't mind just using it as a embark/disembark point.
redhair: like you suggestion too. Is it expensive to fly from Rome to Milan? relative to trains?

It would cost about 100 euros (2nd class) to train from Roma Termini to Malpensa Aeroporto. 4+ hours overall.

If you want to train from city center to city center to explore Milan for a day before flying home, it's about 90 euros (second class) and 3-3.5 hours overall, depending on the train/s. You'd then bus or train to Malpensa for the additional cost of about 10 euros or less, so it ends up about 100 euros either way you do it.

If you fly Rome to Malpensa and then home, you'll go through security in Rome and probably again at Malpensa which will add to the travel time. You'd have to search fares for the day/s you're contemplating. Make sure you understand baggage limits and fees.

Jean - Thanks for the great info.
any hotels to recommend in Rome and Venice? Probably $200 or less per night and not too far from main sights

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