After a Rick Steves tour ending at Lake Orta 4 people will travel to Montalcino for 3 nights then catch a flight back to the States from Malpensa. Need help coordinating travel from Lake Orta to Montalcino and then travel from Montalcino to Malpensa.
Yikes! That's a long trip. Are you sure you're thinking of Montalcino south of Siena? If so, I'd rent a car. I don't think you could pick one up in Orta but you could in Novara which is on the train line south from Orta. Then you could make your way south to Montalcino and then back to drop the car at Malpensa.
I just recalled that your post said you want to begin your travel on a Sunday. That adds to the difficulty because many rental agencies are closed on Sunday. Checking Autoeurope, it looks like their options in Novara are closed on Sundays.
I know that the RS guides help with arrangements for a shuttle from Orta to Malpensa - you could pick up a rental car there on a Sunday, I'm sure. I've already sent an e-mail to RS tours questioning why they would end a tour in Orta because it's very hard to travel from there by public transport - almost as hard as it is to and from Montalcino.
The options by train and bus are very complicated. There are only a few trains a day from Orta to Novara and then you'd connect to Milan. And I don't even want to think about the train/bus connections needed to get to Montalcino. Are you picking up an inheritance there?
There is a train from Milan to Malpensa though. The Malpensa Express from the Cortona station.
Thank you to everyone for your advice. I now see how challenging this excursion will be. It looks as if the best scenario will be to rent a car in Milan(MXP) and drive to Montalcino returning the car to Milan. Is it possible to bypass all major cities on the way to Montalcino keeping to major highways until we get south of Siena. Thank You
You must really like Brunello! So it sounds like the best way is to go in on a shuttle from Orta to Malpensa. Rent a car at the airport and get on the Autostrade to Milan. It will turn into the A1 and take you past Bologna and then south to Firenze where you can get on the S2 to Siena. You'll drive around, not through, all of those cities. You can get directions and a map on www.viamichelin.com which also estimates that it's a 5 hour drive from Malpensa to Montalcino.