Italy July 7th-15th transportation suggestions

Rent the car and return it at MXP. Look at AutoEurope, a broker in Portland. Maine.

I'd want to use public transportation to the maximum extent possible that first day, given that you are likely to be sleep-deprived and jetlagged after the overnight flight. I know I would not be safe to drive from Milan to Montepulciano after a night on a plane.

I think there is at least one rental-car agency in Chiusi, which has rail service and is not far from Montepulciano. I doubt that you could get there before it closes, though. I think the best solution would be to spend the first night somewhere that's easy to reach by rail, then pick up the rental car the next morning, after a good night's sleep, and head to Montepulciano.

I completely agree with acraven. Unless you know how you react to long overnight international flights, driving that far on your arrival day may not be just taxing, but downright dangerous.

As for your return, unless you have a late departure, it would be wise to return to Milan for your last night. Your choice whether to train or drive, but having had a couple of driving trips in Italy, I'd opt for the train.

A lot depends on how safe you would feel driving for almost 6 hours after an international flight. Though I manage to sleep on the plane and rest up before my departure, I don’t think I’d look forward to that drive. Consider taking the train from Milan to Florence (about a 3 hour journey) and renting a car there for the 1 1/2 hour drive to Montepulciano. Yes, you’d still have to take the train and change in Milan. But you’ll be able to rest a bit more on the train ride.

If you do drive, never hesitate about eating at the rest stops on the autostrade. Variety of good, affordable food. Id suggest renting a car through AutoEurope.

EDIT: I just realized you’re arriving on a Saturday. The problem there is that many city or smaller car rental offices are only open until 12 or 1 PM. Europcar, Hertz, Avis and Budget are open till the evening in Florence.

The issue with renting a car upon landing is driving a car for 5 hours somewhat impaired after a long transatlantic flight. I can tell you from experience (since I can’t sleep on planes) that is tough especially because you will be driving for the first 4 hours on a freeway going through flat boring valleys, which can easily put you to sleep at the wheel.

I would consider taking the train to Milano Cadorna station, check into a hotel, and take advantage of the opportunity to see Milan for one afternoon. Then the next morning, rent a car from downtown Milan and drive to Montepulciano.

You could also proceed by train down to Florence (change at Milan Centrale), spend the night, and rent the car the next day to drive to Montepulciano (about 1.5 hours south of Florence). That option would be expensive because the train cost alone for 4 people would be over $200, that is almost the cost of your rental car for a week.

If you insist in renting the cat at MXP, I recommend finding a hotel nearby and chill out the first night. I wouldn’t drive those 5 hours after landing. But everybody is different and maybe you can sleep on planes and be as fresh as a rose when you land.

I sleep pretty darned well on flights, not like at home, but well enough. The flight in is 9 hours (and I plan to be asleep for at least 6 of them)

Any ideas on getting food on the road? Really want to get a decent (for a road trip)meal, not a chain. I have seen that some restaurants close at 3-ish and reopen later.

Looking at the map, I'd assume I'll stop around Parma for lunch.

Most Autogrills are excellent, proper cafes rather than cafeterias in spite of your having to wait briefly at the counter. I remember freshly made to order panani, salads, pasta dishes etc. And of course wonderful Italian coffee. Never a hamburger nor a tired sandwich in sight. Wish North American service centres would take lessons from the Italians! No doubt there are some that are sub-standard; look for the ones with cars parked outside.....Italians know their food.

Italian freeways have rest areas that are fully equipped with restaurants, shops, gas stations, even motels, and you don’t even have to exit the freeway.
Autogrill is the multinational company that has the concession to run many of those rest area cafeteria style restaurants at the freeway rest areas (AREA DI SERVIZIO). They are really good, so take advantage of the convenience. Those are truly civilized rest areas.