First Timer

6 nights? Well, if you dont have your tickets yet, start by planning more time! If for some reason this is all the time you have then immediately take the train to Venice for 2 nights, Florence OR Rome for 3 nights, then spend your last night in Milan.

Wish we had more time...but all we have for this first trip. It is spring break and I am a teacher.

What do you teach? If English, perhaps you might spend a night or two in fair Verona, if history then Rome is a must, if math then finding Fibonacci's grave in Pisa might give you goosebumps, if music then Milan, Venice & Lucca might please you.

I think that if you just have 6 days, it is much better to choose one city so that you do not loose time in transport.
I would go more for Florence in Autumn and Venice if you go in late spring.
Florence has the advantage of having a marvelous countryside all around if you are fed up of the crowd. One hour to Viareggio o Forte dei Marmi if you want to go to the seaside. Florence is milder than Venice.

If you do want to understand Venice you must love the sea. THERE IS NO OTHER TRANSPORT THAN THE SEA.

Did you already buy your plane tickets (meaning you are already locked into Milan)? If not, it's best to go into one city and fly out of another.

Six days on the ground. If you already have your tickets purchased and locked into arriving/departing Milan do this:
Go straight to Florence. Spend all of your time there. Take several day trips, one to Siena and and perhaps another
full day wine tour. There are many, and they will depart @9AM and take you to a vineyard in Tuscany. This will give you the opportunity to enjoy the beautiful Tuscan countryside, as well has having lunch at a winery. Some of these day-tours also
include dinner at an Agriturismo.

If you do NOT already have your tickets booked, and it is possible to depart from Rome, (or arrive Rome and Depart Milan) you will have time for a "taste" of both Rome and Florence. 3 days each place. You will barely scratch the surface for both of these cities, as they are both well worth a week, but you will at least see them. DAL also offers direct flights into Venice beginning in the Spring, so that's another option if you're not yet locked in. Again 3 days in Venice then on to either Rome or Florence.

Remember your last day doesn't count beause you will need to be at the airport early for a US departure. Whe you change locations/cities in Italy you actually lose a half day of your vacation -- check out of hotel, transport to train, ride train 2 hours, transport to new hotel.........You're much better off just enjoying thoroughly what there is to see where you are.

IMHO, after many trips to Italy in the North (family there) I have never enjoyed Milan (I will surely get beat up about this!). It's extremely expensive without having the beautiful antiquities available in Rome, Florence, Venice...........I now arrive in Rome and enjoy at least a few days in Rome before heading North if it's a 'family' trip.

Why Milan?

Fly into Venice, stay 2 nights on the island.

Train to Rome for the rest of your time. You can take a day trip to Pompeii.

Fly home with a desire to get back and see all that other stuff that you missed.

We have not booked our flight, but flying in and out of Milan is about $400 cheaper than any other location. Although Milan may not be ideal, it seems to be the most economical.

Imli, train tickets are not cheap either. $400 each ticket, ok, but $400 combined may not be enough of a savings to make up
for train tickets. You will need to research the train ticket costs.

Thank you Donna. Good to know about train tickets. I will look into that next and see what makes sense.

Where are you flying from? We almost always use open jaw tickets and rarely find it more expensive and sometimes cheaper.

Be sure that you're choosing "Multiple Cities" on the airline website. Some people mistakenly think they need to buy two one-way tickets, and that's always much more expensive.

I would be flying out of Newark. Right now flying in/out of Milan is $689. Multi-city is about $1060. I am now looking into train tickets for comparison. Thanks!

Donna, I don't know where you got $400 for train tickets. Our Milan -Venice legs 58 Euros for 2 first class tickets, 38 Euros coach. Thanks, but i don't need a first class / coach lecture, it's how we choose to travel.

Yes, it appears taking the train from Milan is the way to go. So...I am thinking Venice, Florence and back to Milan?

Imli, JUMP on those airline tickets! I'm a retired airline employee and that's about what we pay! And we're standby. Re the train tickets, I paid Eu 75 a year and ahalf ago for Rome/Florence First Class pre paid. Another EU 75 to return, plus side trip to Venice, etc.........

My thought was that if the total savings was $400 for both people, you can easily spend close to that amount on multiple city train tickets for two people, and if close to that amount, the savings in time for a short trip to Italy might have been worth spending the extra $$ for open jaw flights. In this case, it does not.

P.S. Which airline is offering those amazing fares??? You're on the right track with Venice/Florence rx to Milan for flight home!