13 days starting in Milan

Uh, where are you going? Most places tourists go can be reached by train.

You do not need, nor want, a car while in Milan

You will get better answers here if you provide some specifics

Responders will want to know what other plans, interests, or direction of travel you have in mind. A comparison of car versus train will depend on the next destinations. Trains cover a lot of territory. A car gives you full flexibility of destination and schedules, but you'll usually pay to park it everywhere you go and can't always navigate right to the door of your hotel.

Rick typically recommends taking a train into Milano Centrale station (1 hour) and then connecting there on a regional train (1 hour more) to Varenna on Lake Como, which is a very pretty and relaxed spot to get acclimated to Italy. See itinerary suggestions at https://www.ricksteves.com/europe/italy which are fleshed out with lots of useful detail in Rick Steves Italy, the book.

First thing to nail down is the number of nights you will be there. That will determine how many real days you have.

Personally, we'd take the train from Milan to Lake Como for a couple of just to get acclimated. Then head to Venice and after a few days there go to Florence. Wind up in Rome and fly home from there.

Try to plan on stays of at least three (or more) nights in each place. The reason for that is it always takes more time than one anticipates when changing locations, and that is simply time lost that can't be regained.

I realize this is very general, but without knowing your exact time frame and interest it's hard to be very specific.

With regard to renting a car, I'd try to avoid it as it is simply a big hassle and the trains work wonderfully well in Italy. If you must rent a car, you might want to reconsider renting a car right away. Take the train to the first destination and rent the car there the next day or when you are ready to leave. Jet lag (no matter how well handled), lack of sleep, not being familiar with the local road system, can all be a problem. There are some that are not bothered by any of those things. Others think they are ok but are really driving somewhat impaired without realizing it. And some folks are complete zombies and should never drive on the day they arrive.

Just something to think about.

If you go immediately to Lake Como, you can take ferries and buses to the towns along the lakeshore. Then train to Venezia, where you also won't need a car.

Personally, I think trains and buses will work for you. You can pay more attention to the kids, and their experience, since all of you will be passengers (no driver-navigator team).

Hi Aaron
We drove for a whole month in Italy 2006 and will be doing it for 15 days next year. It was great but times have changed with more ZLT zones and more cars. We even drove it into Rome which was fun as I had to jump out and ask directions 3 times to our drop off spot.
In the meantime we have been back 4 times to Italy and have used the trains.
If you decide on driving the Michelin Map is a wonder. I am using my ripped up one as I sit hear mapping out our next driving adventure
I agree with Laura, jet lag will get you, so take the train for the first week. Certainly to Lake Como and Venice. Depending on the time of year you are travelling - summer is the hottest and busiest I would plan now for next year and certainly read RS book on Italy.
This site is wonderful and with more info as to your timing going from the North(Lake Como- Venice) to the south (Amalfi) and back to Rome is time consuming.

Thanks everyone for the input. Here are more specifics...

We are going as a family of 5 in early October and we will be there for a little over 2 weeks. My wife and I spent about 7 weeks in Italy when we were in our 20's so we feel like we've seen a lot of Italy ourselves. This trip was intended to introduce the kids to Europe. We thought they would love Rome and Venice. We thought a hill town or two would be interesting for them and we were hoping for some pool/beach time for the girls to relax with no sight seeing. We love the Cinque Terre, but don't think we can do that and the Almafi coast in this trip. We thought the weather might be better in Almafi than the north. While we didn't make it to Como in our first trip, we thought given the weather might be cool that time of year, so that probably won't make it for this trip either, unless people think it's not to be missed.

We are flying in/out of Milan. Debating if we should go immediately to the south via plane or train and then work our way back up or the reverse.

The debate about train/car is really about costs and pool time -- we thought purchasing 5 train tickets may be expensive and a car might be more economical. Plus in Tuscany/Umbria and Almafi we thought we would stay outside of town so the kids could have some pool time again, so we figured we needed a car to get to the hotels or AirBnB's that have pools.

I'd stay Rome and north. The Cinque Terre are pleasant in October (we've been 4 times in October). A lot of agriturismi close their pools by October. Not sure hotels will have them open, either. From where do you fly out of Italy?

If your flights are set and unchangeable then I would suggest going to your farthest point at the beginning of your trip and working your way back to your departure point for your return trip. Much less stress than making a mad dash from a distance to catch your return flight.

I sure hope you bring a nice gift back for your kids teachers. They will deserve it for having to make the special accommodation their missing 2+ weeks of school, will necessitate.

Joe -- our school has a break in october so we figured it was a great off-peak time to travel.

Flights are set as we got them with miles, so there isn't much flexiblity there.

Well, I for one still like the idea of going from Milan to Lake Como at the beginning of the trip for a couple of days just to get acclimated. Then head to Venice and after a few days there go to Florence. Wind up in Rome and take the train back to Milan to fly home from there. My thinking is that flying from the U.S. to Milan and then going to Rome all non stop at the beginning of the trip will be awfully long and tiring. And then you start of in hectic (but wonderful) Rome. Better, in my opinion, to introduce the girls to Italy gently.

We are thinking about Seina/ Civita to our trip. Would kids enjoy that or should we take it out? We will not rent a car in Rome or Venice but would it be a good idea to rent a car in Tuscany? I'm think in the smaller towns finding parking would be that difficult. Any thoughts? Once getting to Milan we hear Ryan air have cheap flight to fly to Sorrento. Is a Ryan Air reliable?

Haven't been to Civita but did spend a day in Seina. Our main interests there were the places we were able to visit that are connected to the annual horse race. It is a university town and has some interesting architecture and back streets to explorer, but I'm not sure how much is there that world really be of interest to the girls. Perhaps someone with daughters that age can shed a better light.

My thoughts are that you're already at the airport. Easyjet has 4-5 flights a day from MXP-NAP. Surely one would fit your schedule. Even if you sit at MXP for a few hours it's better then the train. Very reliable, but check baggage allowances carefully. Flight is 1hr 25min.
Then from NAP take the Curreri Viaggi bus to Sorrento.
75 min. 10 euro.
While Sorrento is not the AC, it is by far the best transportation hub. Consider adding a day here if you get in late.

From here to Rome by Circumvesuvian (67 min. )Then train (Trenitali) Napoli Centrale-Roma Termini 70 min.

From Rome, head to Orvieto.
1H17m. Spend 1 or 2 nights.
Several towns you can hit by regional trains. Then head to
Venice.

Not using a car this trip will allow you more time to interact with the girls.

Train from Malapensa to Sorrento is over 7 hrs.

aaron,

A few important points to note regarding car rentals in Italy.....

It's important to note that for driving in Italy, each driver listed on the rental form must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. (so you must carry both). These are valid for one year, and easily obtained at any CAA/AAA office (two Passport-sized photos required, which may be provided by the issuing office).

You may never be asked for an IDP, but failure to produce one if requested can result in fines on the spot! Failure to pay the fines on the spot can result in the rental car being impounded (which will result in further financial penalties). Have a look at https://www.ricksteves.com/travel-tips/transportation/rental-car-requirements for more information on I.D.P's and driving in Italy.

You may also want to have a look at some of the posts on the forum concerning the dreaded Zona Traffico Limitato (limited traffic) areas that are becoming increasingly prevalent in many Italian towns & cities (especially Florence!). Some of these are enforced by automated cameras and some by local police. Each pass through one of the automated Cameras will result in a €100+ ticket and visitors often don’t know of these violations until several months after they’ve returned home. In addition to the actual fines, renters will also be charged by the rental agencies for providing information to the authorities. You may find this website helpful - http://www.slowtrav.com/italy/driving/traffic_cameras_speeding.htm

There’s also the possibility of fines for driving in bus lanes, parking tickets, tolls and speed cameras including the devious Traffic Tutor system which not only monitors instantaneous speeds but also average between two points. Violate either or both parameter and expensive tickets will follow!

Using the excellent rail system (especially the high speed trains) will be a much easier and more efficient travel method.