First trip to (Northern) Italy - please suggest itinerary and stops

With the amount of time you have, and being first-timers, including just Venice and Florence sounds perfect. Perhaps you might want to go to Venice first, and get a respite from cars. You might want to give Florence more days, to allow for a day trip to one of the hill towns for your beautiful views of the countryside. Then, you need to plan a return trip! Have a lovely time!

Also, the trains are the way to go - no need to mess with renting a car.

Definitely agree that you only have time for 2 locations and I would agree with previous poster that Venice and Florence would be the way to go based on your stated likes of art, history, food and wine.

Depending on when you arrive in Milan you could take a train (about 1-1/2hrs) directly to Venice from there and stay 4 nights with a day trip to Padua or Verona (or both). Then transfer by train (2-3 hrs) to Florence and spend the rest of the time there with day trips to one or more of Siena, Lucca, Volterra, Cortona. Train back to Milan early on the 21st with time to maybe see one major sight before heading to the airport for your flight home. Or you could return to Milan on the 20th for 1 overnight before your flight the next day, that would give you a little more time to explore Milan, it is definitely worth a day.

In looking at this forum, it seems we should be able to connect Venice with Florence, and Florence with Milan via high-speed train, but that doesn't reflect what I find on trenitalia.com. Is this because of the remoteness in time?

Yes. Italian trains post schedules 90-120 days out, but there's a twice yearly schedule change, and at those times schedule posting gets delayed.

Does anyone know for sure that it can be done? If so, can you give me some idea of the amount of time it takes?

Yes, it can be done. To find schedules and times, choose a date about a month ahead, on the same day of the week as you will be traveling (although trains on these major routes aren't that different on Sundays). You'll see that between any two of these three cities, it's about 2.5-3 hours.

Would it be more efficient to do one or both of these by renting a car?

NO. The trains go at 250-300 km per hour; no car can touch that. These roads are also very congested, with lots of trucks, and are neither scenic nor fun (think New Jersey Turnpike). Then there's the issue of what to do with the car in Venice (expensive) and Florence (potentially VERY expensive if you wander into a ZTL accidentally).

Our initial thought is to fly into Milan and immediately train to either Venice or Florence without staying overnight, explore wherever it is, then move on to the other, and travel back to Milan early on the day we fly out. Would you choose one over the other first?

That's a good plan. It doesn't really matter which one you choose first. But you should plan to be back in Milan the night before. It takes an hour to get from central Milan to Malpensa, and you really do want to be there 3 hours before departure, and if there's any delay on the trains, you'll miss your plane. If you don't find anything in Milan you want to see, you can get there late the night before your departure. But do look into spending some time there - I find it quite underrated, if not like the "Italy" that most visitors come to see.

will we miss something either quintessentially Italian or completely unique if we do not go to Cinque Terre or Lake Como?

You will miss whole swathes of Italy with your itinerary - and that's fine for a first visit with limited time. Don't focus on what you can't see - focus on getting the most out of what you are seeing, and leave the rest for your future trips. If you're like most of us, there will be many of those!

From Florence you can daytrip easily by train or bus to Siena, Lucca, and Pisa. From Venice you can daytrip by train to Padova, Vicenza, and Verona. On a short trip like yours, this is the best way to get out of the big cities.

Thursday 13 October
Arrive Milan at 1215. Train to Verona - 1 night

Friday 14 October
Train to Venice - 3 nights

Monday 17 October
Morning train to Florence - 3 nights (day trip to Siena)

Thursday 20 October
Afternoon train to Milan - 1 night

Friday 21 October
Depart Milan at 1610

Ken has a great plan. Go directly from Milano Centrale to Venezia Santa Lucia, then from VSL to Firenze Santa Maria Novella, then FSMN to Milano for your last night. Lots of good hotels near Milano Centrale and eat transportation from there to the airport. Only three different check-in/outs.

I'm so appreciative of all the advice and good suggestions! You've given us much to think about and many practical tips.

You will have seven full days and a part of two other days. With that in mind, consider staying overnight only in Venice and Florence -- about half your time in each. You can do interesting day trips from both of them, but they both have enough themselves to keep you busy the whole time you are there. No need to rent a car for that short period of time -- the trains will get the job done quite well.

Good advice above. I would choose Venice first - it's the perfect place to soak up the atmosphere while you get over the jetlag and catch up on your sleep. If you want to add a place, you can stop for a day in Verona or Padua - take an early train out of Venice, store luggage at the train station, and an evening train to Florence. My preference would be for Verona, but Padua is about an hour less train time.

Harold's right, of course. There are worthy sights in Milan too. The Duomo's exterior is lovely, day and night, and wandering on the roof among its carved pillars is like nothing else. Next door is the beautiful Galleria Vittorio Emanuele II, just beyond it is La Scala. With a little more time, the Sforza castle and its museums is not far at all.

Zoe, Chani and Harold have you on the right track.

Just wanted to mention that if you want to see the major museums in Florence (the Uffizi and the Accademia) without spending forever waiting in line to get in, be sure to buy tickets in advance online. Not an issue with the smaller museums, which are also wonderful.

Layni,

You've received lots of good information and hopefully you've got your travel plans sorted now. A few additional thoughts....

I agree with the others that you don't need a car for the few places you'll be going. Travel by high speed train will be far quicker and far easier. However as this is your first trip to Italy, you'll need to be aware of the potentially expensive "caveats" regarding travel by train and other public transit in Italy. If you need more information, post another note.

You'll also need to know the specific stations you'll be using, and the Italian names for those. Many cities have more than one station, so that's important information to know. For example, your destination in Venice will be Venezia Santa Lucia, in Florence it will be Firenze Santa Maria Novella and in Milan you'll use Milano Centrale.

I would highly recommend having a look at the RS Italy 2016 guidebook, as there's an enormous amount of good information there that will help planning your sightseeing. The information in the book will save you both time and money. You might want to pack the book along, as it's a good resource to have during travels. It also has information on good hotels, restaurants, etc. If this is also your first time in Europe, you might want to read Europe Through The Back Door prior to your trip.

I'm not sure you have the time with such a short time frame, but during your stay in Florence you could take a day trip to the Cinque Terre. It's about 2-3 hours each way, with a couple of train changes but not overly difficult. It will likely be "quieter" in the C.T. at that time of year, so you may not have to contend with the hordes of cruise ship day-trippers. Provided the weather is good, it should be a really nice day, and you'll be able to enjoy some exceptional Pesto meals in the area where it was invented, along with some great seafood if you like that. If you do decide to take a day trip there, I'd suggest ending your tour of the five towns in Monterosso, where you can enjoy a fine meal before heading back to Florence in the evening.

Lago di Como would be more of an outlier, and while you could also spend a few days there it would have to be at the expense of one of your other locations.

I'd suggest spending the bulk of your time in Venice and Florence and minimal time in Milan. Allocate more time to Florence to allow time for day trips. It's very easy to make a day trip to Siena or Lucca from there. You could consider 3 nights in Venice, 4 nights in Florence and 1 night in Milan (prior to your flight home).