A Month in Italy, train/car questions

I'm not sure I understand the whole plan (like whether the mom is picked up before or after the Last Supper).

In any case, if you intend to spend any time in Milan, it is better not to have a car while in Milan. You should rent a car after you leave Milan to head to Tuscany (Siena).

The Monday after Easter is a holiday in Italy. In any case where are you staying? Positano has no trains. From Positano to Naples airport I'd recommend a car, especially if the flight is early. There is a bus that goes to the airport from Sorrento, but if the flight is too early it won't work. A private car ride (like a limo service) is what I'd recommend (unless you keep the car while in Positano, in which case you can drive your own).

Be aware of the ZTL (Limited Traffic Zone) in any city center. Cars are not allowed except for residents with permit.

You are staying a long time in both Siena and Positano. I'd probably choose to stay no more than one week at each location, but that is me.

lotus,

With 4 adults and 2 children, I'm not sure a rental car is going to be best idea. You'll have to rent a large vehicle to accommodate that many people with luggage.

You'll also need to be aware of the usual potentially expensive "caveats" when driving in Italy. For example, 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. 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). Failure to produce an IDP if requested can result in fines on the spot! Have a look at https://it.usembassy.gov/u-s-citizen-services/local-resources-of-u-s-citizens/transportation-driving/ for more information on I.D.P's and driving in Italy.

As Roberto mentioned, you'll also have to contend with ZTL (limited traffic) areas. You may want to have a look at some of the other posts here concerning the dreaded Zona Traffico Limitato that are becoming increasingly prevalent in many Italian towns & cities especially Florence, which is almost saturated with automated ZTL cameras. EACH PASS through one of the automated Cameras will result in a €100+ ticket, which you won't know about until several months after you return home! This website provides more information - http://www.slowtrav.com/italy/driving/traffic_cameras_speeding.htm . I received a note not to long ago from someone who had received ZTL tickets in Italy, and as I recall the cost was over $700 by the time the dust settled.

There's also the issues of parking tickets, high fuel costs, tolls and automated speed cameras including the devious Traffic Tutor system which measures not only instantaneous speed but also average between two points. Violate either or both parameter and expensive tickets will follow.

There are also some "caveats" when using trains and other public transit in Italy, but those are very easy to deal with once you know the rules. Using well planned trains is usually the easiest method of getting around and much more efficient than a car on those routes served by the high speed trains which travel at up to 300 km/h.

You should plan to spend at least one night in Milan if the Last Supper is a must-see for you. What time is your mother landing? If it's in the afternoon/evening, then you won't be able to see it on the 4th. If she lands in the morning, you won't have time to get to Milan and then out to the airport in time - and she may be too zonked to enjoy it anyway. So you may even need 2 nights in Milan. Take the train to Milan and go to your hotel to drop your luggage. Then one adult should take the kids somewhere in Milan while the other adult goes to the airport to pick up your mother and take her and her luggage to the hotel. There's little point in taking the kids to the airport. It's an hour each way plus all the waiting at the airport.

At what point does the 4th adult join you? For how long? Besides all the important info Ken has given you, bear in mind that in general European cars are smaller, so things like garage parking spaces are also smaller. The larger the car, the harder it will be to drive in narrow Italian city streets and to find parking. Use viamichelin.com to estimate driving times. For instance Siena to Assisi (albeit probably the longest trip) is nearly 2 hours each way without traffic or pit stops or wrong turns. Even one adult and 2 kids is kind of crowded in the back seat. There's not a very good view from the back seat ever, and from the middle seat, well, nearly none.

If you want to see Pompeii, Vesuvius, Capri, even Naples, on day trips, Sorrento is where you should base. Maybe split your time between Sorrento and Positano.

How old are your kids?

You could also consider Salerno as a stop so you can visit Paestum. Your kids might enjoy walking through the ruins, and perhaps a visit to a mozzarella farm. Paestum also has a good beach and a very good museum; if you want to relax for a few days, you could do that easily there. Most hotels and B&Bs have onsite parking.

From Salerno, you can take ferries to the towns along the Amalfi Coast.

I agree with Chani about the airport pickup - one parent can take the kids to the Duomo (go to the roof for some time with the gargoyles), walk through the gardens at Castello Sforzesco and visit the Castello if you have time.

I would take the train from Venezia to Milano, very easy and if you get super-economy fares you will pay about €10 each.

Car rental offices are located inside Milano Centrale train station, pick up your car on the way out of the city.

You are staying a long time in both Siena and Positano. I'd probably
choose to stay no more than one week at each location, but that is me.

I'll echo Roberto here; 10 and 14 days respectively is a really long time. I'm curious why you chose to do that if the plan is "touring the country"? Even a full week in Positano would personally be too much for us (and 4 days in Rome would not be enough). A month gives you the opportunity to settle into a few more locations without feeling rushed.

That aside, I'd probably have chosen a location with train service if staying that long and planning to do a lot of day tripping.

as far as picking up your mother. How about this. All of you take the train to Milan, but only you go to the airport and bring her back to Milan to meet up with family. That gives the family some time to see something. Then go on from there. That's what I would do.