Train from Milan Malpensa airport to Cinque Terre (and then to Venice)

Take it a step at a time. Use bahn.de or trenitalia.com for scheduling information. Schedules for May 15 will not be posted until around the first of the year so use the same day of the week in Dec for both schedules and pricing if you use trenitalia.com. Schedules change little from quarter to quarter. Second, Milan is a city, Cinque Terre is an area. To look at train schedules pick a town in Cinque Terre. The train from the airport to Milan is a private line. From Milan on it will be trenitalia. Without looking at the schedule myself, I would assume a train change on either Regionale or ICs. But that is quickly determined by looking at the schedule. The is no advantage to buying Regionale tickets on line - in fact - there is a big disadvantage so buying at the airport or Milan works. A car is big disadvantage in CT because of parking problems. I would also go to Venice via train since cars are prohibited from driving on the canals.

Cars can be a big liability in many ways if just going city to city. You should plan on using a car if staying at B&Bs in the countryside. I am guarantee you that you do not want to be driving a long distance on Italy roads after an overnight from the US.

Just did a little quick checking. This is ball park. Milano to La Spezia, mid-Jan on a Wed, is 3 hrs, 11 minutes via IC with base fare of 28E. Could be as cheap a 9E for Super Economy ticket but this is a no change no refund. Now you could gamble a bit. Book the Super Economy for around noon from Milano. If you miss it, you miss it, and have to buy a regular ticket for 28. Is saving 19E worth the gamble? You decide.

The trains from Malpensa to Milano Centrale (the station you want) run twice an hour and take about an hour and cost 12 euro per person. So just take the first train after you get your luggage.
There are direct IC trains from Milano Centrale to Monterosso, one of the five towns in the CT. The schedule for May is actually out now (next change mid June 2015), but you can't buy tickets until 120 days prior. Yes, there will be 9 euro nonrefundable fares available in 2 months. If you want to go to one of the other towns in the CT, you can change to a Regionale train there, or at the IC train stop in Levanto. Monterosso is the only place the in the CT that IC trains stop.
IC trains are mainline trains with 1st and 2nd cl cars as well as a bar/snack car. The tracks to Monterosso are not set up for the high speed trains, so the ones that run this route are not any faster than IC trains, and they do not stop in the CT, requiring a connection no matter where you are headed.
Train to Venice is the way to go. You should be able to get nonrefundable tickets for 18 euro per person. takes about 6 hours.

You do not want to drive from Milan to Cinque Terre. The coast road is narrow and goes through tunnels much of the time. And you can only drive as far as Monterosso, the northernmost of the five towns. The other four are car-free, so you must pay to leave your car in a lot above town. And finding those lots can be tricky. When we were hiking Innthe hills above Manarola, we saw a car go by a confusing intersection nearby several times. Finally they stopped and asked if we spoke English, and then if we could direct them to Vernazza. Their GPS had tied them in knots. I pulled out our hiking map and showed them where we were on the map,,but it was not clear how they would get from there to Vernazza through the network of curvy roads. I hope they made it!

The trains are easy, cheap, convenient, and comfortable. There is a direct IC ( InterCity fast train) from Milano Centrale to Monterosso every day, departing a little after noon. I suggest you take that one,Mather than head to La Spezia, which is not one of the five towns but is the gateway to Cinque Terre from Florence, Pisa, Rome, etc. Most other trains to Monterosso will have you make an additional change at Genoa. After your long flight it will be easier and more restful to take a direct train rather than having to get off and on another train. Like Frank I suggest you consider booking that train in advance to get the Super Economy fare. You should have no trouble making that train unless your flight from the US is really late.

At Monterosso, you change to a Regionale train for the very short ride to your village. Since this is an anniversary trip, I suggest you look at Hotel La Toretta in Manarola. Room 6 has a large balcony with a view of the sea and the vineyards, and a cascade of bouganvillea from the terrace next door. ( The steps up to this room are steep, I should warn you). The host is very gracious and there are amenities that are not mentioned on the website, like free minibar, afternoon wine tasting on some days, and a welcoming glass of prosecco when you arrive. They will make dinner reservations for you at the best place in town ( Trattoria da Billy) and you will be treated very well there.

I was posting at the same time as Sam.

And I agree with his advice to take the train from CT to Venice as well. Wait to pick up your car until you leave Venice. You can pick one up either at Piazzale Roma or the Venice airport. Compare the rental costs. And if you pick up at Piazzale Roma, be careful to observe the speed limit on the bridge. Nthere are three speed cameras on the bridge and they catch a lots of unwary drivers.

Theresa,

It's actually a very easy matter to get from MXP to the Cinque Terre. To begin with, I assume you're arriving at Terminal 1 on a flight from the U.S.? If arriving at Terminal 2 on a regional flight, the procedure will be slightly different.

Aside from the other issues, there's NO WAY I'd want to drive in a jet lagged state after getting off a long international flight. Having a car in the C.T. is not advisable, as it will sit in a car park gathering dust and costing you daily parking charges.

This is the route to follow.....

• After you've retrieved your luggage, go to the airport rail station and buy your tickets from there to whichever C.T. town you'll be staying in. Monterosso is the easiest, as there are direct trains from Milan. You'll be issued two tickets. The first one is for the Malpensa Express, which will take you to Milano Centrale. Note that the M.E. has two destinations, Milano Centrale or Milano Cadorna - BE SURE to board the correct train! Also, you MUST validate your ticket prior to boarding the train, or risk hefty fines which will be collected on the spot! The second ticket will be from Milan to the C.T., and the trains may be Regionale (validate your ticket prior to boarding!), InterCity or Freccia. The latter two trains have compulsory reservations, so you can ONLY use the train specified on the ticket (or again, hefty fines!).
• Use the bahn.de or Trenitalia websites to get some idea on the departures and train composition at about the time you'll be arriving. NOTE that schedules for May won't be on the website until some time in December, so just use the same day-of-the-week that you'll be travelling, and that should be a good estimate (they probably won't change much).
• For the trip from the Cinque Terre to Venice, train will be the quickest method, but some changes will be involved so be sure you're up to speed on how that works. There are two main routes you can use - either through Milan or through Florence. Of the two, my choice would be Florence. Using Monterosso as the departure point, one of the easiest trips will be a departure at 09:01, arriving Venezia Santa Lucia at 14:20 (time 5H:19M, two changes at Pisa Centrale and Firenze SM Novella). The first and last trains on that route have compulsory reservations, which will be supplied with your tickets if you buy locally. The middle train is Regionale, so you'll need to validate prior to boarding the train on the day of travel.
• For the trip to Venice, if you're willing to commit to a specific train and departure time, you can purchase those tickets online. I'd suggest trying Italiarail.com, as their website is a bit more "user friendly". You can also buy the tickets locally, if you'd like to have a bit more flexibility in when you travel. Monterosso has a full-service ticket office, so if you're staying there it will be easy. I haven't checked recently, but the other towns also have ticket offices (possibly more limited hours), or they may use ticket Kiosks.

I usually try to time my departure from Milan to Monterosso so that I can connect with one of the direct trains, as that's always a much easier way than having to deal with multiple changes (especially when jet lagged).

Buon Viaggio!