If you're planning to visit Piedmont (you would really need a car for the wine region), I would fly into Milan first. You don't have as much time as it seems unless your 12 days doesn't include flight days.

With 12 days on the ground (I assume you mean you have 14 days, but 2 are travel days to and from Canada?) I would pick 3 places. As Venice and Piedmonte are on opposite sides of Northern Italy I would pick 1 - probably Venice as you dont want to rent a car, which is really required for Piedmonte countryside.

I would fly into Venice spend 3 nights, train to Florence spend 4 nights with a day trip to Pisa and potentially a private tour to wineries for a day, then train to Rome and spend the remainder there flying home from Rome.

Thanks for the response kybourbon. My trip is 14 days total with two days set aside for travel to and from Italy - so 12 days to travel around Italy. I'm wondering if it's possible to book a day tour from of one of the major cities (maybe Milan or Turin) to Piedmont that would include a driver?

I think Jamikins nailed it for you. It is an excellent time of year to be there. You will love Italy.

Thanks Jamikins. Your suggestion sounds more doable. I'm also curious about trains/buses. What type of transport pass is best to purchase?

Generally its better to book your trains directly with Trenitalia - you can see schedules and pricing here:
www.trenitalia.it

Thanks again Jamikins. I just looked at the site. Should I book before I go or just book when I arrive?

CT100,

I think most who contribute to this site would agree the Trenitalia site can sometimes be "temperamental". If you have some flexibility in your schedule, meaning the time of day you could leave one destination to get to another, in my experience you can by tickets the day you travel or a day or two before. For example, using Jamikins suggested itinerary starting in Venice. Before you start your site seeing swing by the train station and purchase tickets to Florence to leave at your chosen time and day. When you get to the Florence train station, you can do the same for your next stage to Rome. Venice to Florence and Florence to Rome are popular routes with many time options so I do not think it will be an issue to wait and buy "in country"

My wife and I made our first trip to Italy 4 years ago with a similar itinerary and bought tickets after we got there with no problem.

While I certainly agree that you should not try to see everything on your list, I don't think you necessarily have to rule out Piedmont. After all, you would not drive to a wine tasting would you? I only weigh 115 lbs, so even driving after two-three glasses of wine at dinner is out of the question. Of course you will not see every nook and cranny of Piedmont, but it would still be quite enjoyable and you could likely book drivers or tours for winery visits.
I just wanted to add that 2cents, especially considering fall is so perfect for Piedmont, but regardless I strongly advise you to pick three (4 max) places for your trip.

I'm with jamikins. You might be able to find a wine trip from Venice to the Piedmont area. Other Fodorites??? If so, take a day from Florence. Otherwise, you should have no trouble finding a Tuscany wine/food tour out of Flo.

Since you listed Rome last, one other possibility is to fly into Venice and out of Milan and skip Rome. For me, missing Rome would be terrible but it IS a big city.

CT100, you have received good advice about sticking to 3 places. You really don't want to spend all your time packing/unpacking/traveling. You are only in Italy for 12 days... trust me, they move really fast. You want to "experience" it and then remember the experience after you are home.

I agree that flying into Venice and spending 3 days, then on to Florence for 4 (you can most definitely book a wine tour to Chianti or elsewhere in Tuscany for a day from Florence). Then train to Rome and depart Rome for home.

I've done this 3 times and it works well, imho.

Buon viaggio! You will LOVE Itay!

Thanks everyone for the info. I booked my flights. I'll be in Italy a little longer than originally planned. 14 day to enjoy Italy plus two travel days. Here's what I'm thinking for an itinerary:
fly into Venice - stay 2 nights - rooms are booked
take a train to Cinque Terre - stay 2 nights (any suggestions of where to stay here?)
take a train to Florence - stay 7 nights at a B&B
take a train to Rome - stay 3 nights
fly home from Rome
All input is appreciated. Thanks

Your flights are sensible, but I would do more nights in Venice and Rome, fewer in Florence which has wonderful things to see but can get tiring with the hustle and bustle of too many tourists. Two nights is plenty for the CT.

Yes, considering you'll be jetlagged for a day or so when you arrive in Venice, you're cheating yourselves there. Two nights is one day, in Venice and in the Cinque Terre. And, unless you're huge fans of Renaissance art and architecture, why so many days in Florence?

The Cinque Terre is an outlier on this trip. Did you know part of the trail between the towns in closed due to a horrendous mudslide last fall? And the weather gets iffy again in October. There's no point going to the CT if it rains.

So I'd drop the CT, add those days to Venice, take a day or 2 off Florence and add to Rome. If it were my trip.

If you want to visit wineries, you can always hire a car and driver. DH and I did this one time when we were staying in Florence. I don't recall the exact cost but for a full day out it was somewhere around 200 euro. Well worth the money, IMHO. We arranged it through our hotel.

I agree with tarquin and Mimar. Skip the CT this trip and/or cut some days off Florence to stay longer in Venice and Rome.

I love Florence, but 3 days would be good.

Are you driven to choose a destination because of history...art & museums...food & wine...or fantastic scenery?

You will find amazing views, art and history in Venice. I agreee that you may want 3 nights there. Train it to Florence for art and archetecture for 3 nights. This is where you might want to try a cooking course in a food/wine/fantastically scenic location in Tuscany or Umbria...or ? .assume 2 or 3 nights in that location...then finish up in Rome.

Here is one site to look for potential cooking class experiences. http://www.italycookingschools.com/
Here is another http://www.cookinumbria.it/. I seriously considered these while planning our trip last year, but then we just decided to spend 2 weeks in Umbria with a car, and never got around to a cooking course ( although boy, did we cook up a storm!)

I do agree that 7 nights is a long time to stay in Florence. Maybe you intend to use it as a base to also visit surrounding cities like Siena, San Gimignano, Volterra or Pisa, and maybe a visit to wine-tasting agriturismo in the countryside of Tuscany? - then maybe that would be fine.

If you decide to omit Cinque Terre, then I would stop instead for three days on your way to Rome (lessening one day in Florence) in Umbria, where you can visit Gubbio, or Assisi, or any other beautiful place in Umbria. In my opinion, the scenary in Umbria is as beautiful as Tuscany, if not even more.

CT100,

Stick with the original advice from Jamikins of narrowing your stops to 3 destinations. THe last few posts of suggesting Umbria, Assisi etc are nice suggestions but add additional logistics and could dilute your time even further. As unbiased as I can be, (I am planning my 3rd Italy trip in 4 years) I like the Venice, Florence, Rome itinerary. I further support Mimars idae of a day or two more in Venice and Rome. Florence is (for me) a wonderful place. I have been twice and will go back; however, it can wear on one becasue of its popularity.

I am using "hills and roads" tours to drive us from Florence to Rome. They will do wine tour and sightseeing on the way. Have booked car and driver for the day. Seemed a good way to combine a winery tour with a day of travel and saves lugging bags on the train. Just a thought.!

Absolutely add another day to Venice. It is not a place to rush and see, but rather a place to experience.

Unless you are nuts about Renaissance Art and plan day trips, cut Florence to three days and give a lot more time to Rome.

Since you now have 14 days on the ground, unlike others, I actually would pick another place to spend a couple of nights, perhaps Bologna or some town in Tuscany. I agree that Umbria is lovely and Assisi is very special, but it is a bit easier to reach several towns in Tuscany from Florence. I mention Bologna because of your interest in food.

So might look more like this
Venice: 2 &1/2 days, 3 nts
(only if you are arriving early. If you are ariving late in the day, add another day and nt to Venice)
Bologna: 1 & 1/2 days, 2 nts
Florence: 3 & 1/2 days, 4 nts (One day trip, wine tour, etc.)
Rome: 5 & 1/2 days, 6 nts (day trips possible)

or

Venice: 2 &1/2 days, 3nts
Florence: 2 & 1/2 days, 3 nts
Siena or another Tuscan city: 2 & 1/2 days, 3nts (wine tour or cooking class one day)
Rome: 5 & 1/2 days, 6 nts (day trip possible to Orvieto, Ostia Antica, etc.))

I figured half days beause of travel and check in time.

With 14 days, this leaves an extra day for you to add wherever you might like.

Extra time in Venice would be great because you will have some jet lag and there are great, easy day trips from Venice (Vicenza, Padua, even Verona), if you are really "done" with Venice in two days.

was in Italy last month- here's how we did it: Venice, 5 nights; Bologna, 3 nights (day trip to Ravenna); Rome, 5 nights. Loved it all!

I did book our train tickets ahead, some of the fares were quite good- like the 9eu mini fares on one of the legs.

It can be stressful to catch trains and reach hotel and then just spend two nights in any particular place. If you were driving, that might be a different matter.

Since you say you have 16 days, I am assuming you have 15 nights' accomodation, I always like to plan according to night stays because of accomodation. I would plan my holiday as follows, taking into consideration that you prefer to stay the longest in Tuscany (Florence being a city in the region of Tuscany):

Venice 3 nts

Bologna 3 nights - taking a day trip from there to Rimini or Ravenna, (maybe a visit to Mosaics or Italy in miniature park in Rimini, there is even a nice big Aquarium in the vicinity which my kids loved) or even a visit to a coastal town in the border of Le Marche - last December we were in Rimini and in half an hour's drive we went for lunch in Pesaro in Le Marche. Alternatively you can base yourselves in a hotel in Rimini. We did this and stayed in a hotel on the coast with lovely beach views in Rimini called Terminal Palace Hotel. It is a newly-opened hotel, email directely to hotel if interested so they might give you a good deal, especially since you are going out of season. We were there only for 2 nights, so sadly we did not manage to also fit in Bologna, but it is on my toplist. That is why I would suggest you stay in this region for 3 nts.

Florence 5 nights - you can do a couple of day trips from there to visit Siena or San Gimignano or Volterra or Pisa and a day for wine tasting or cooking class at an agriturismo in the amazing counryside. Bear in mind that Florence is a very busy city, always packed with tourists, it was so even when we visited in December, so you might consider basing yourself in another town and city in Tuscany and going for a day to Florence. But if you prefer to find accomodation in this beautiful city to spend more time there, then of course it is up to you.

Rome 4 Nights and spend your days sightseeing in Rome - or maybe, if you prefer not to stay all the time in Rome, take a day trip to Orvieto or Ostia Antica.

Catch plane back home from airport in Rome

But I guess each to his own preferences.