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4 days Milan to Rome - Need help re places to visit and car pickup/dropoff

My husband and I will be returning to Italy in late May and are trying to decide how best to spend our travel days before meeting up with the rest of our party in Rome. I always try to pack in way too much and am trying to rein myself in!

Here are our travel days -
Wed, May 25 - Arrive Milan Linate at 5:10 pm; get settled in hotel; have dinner; maybe walk around Galleria Vittorio Emanuele II
Thurs, May 26 - Tour the Duomo early; walk through the Galleria if not done the previous evening; leave Milan by train to ?
Fri, May 27 ?
Sat, May 28 ?
Sun, May 29 ?
Mon, May 30 ?
Tues, May 31 - arrive in Rome late morning to meet family arriving from US; check into apartment

In 2014, we were in Italy for 3 weeks and visited Lake Como (Bellagio, Varenna); Venice; Florence (with day trips to Lucca, Pisa, and Siena); and Rome (with day trip to Orvieto).

Initially, we considered including Bologna (with a day trip to Ravenna to see the mosaics) and perhaps Assisi. We would love to see the Cinque Terre but my knees probably preclude the hiking/climbing required to do that.

Now we’re simplifying and are considering taking the train from Milan to somewhere in or near Tuscany, picking up a car to drive through Tuscany and perhaps Umbria, and dropping it off somewhere before taking a train into Rome. We prefer automatic transmission so probably need to pick up from a major location (like an airport) but don’t want to have to drive through a big city after picking up the car. We love wandering through small towns and think this option might be more relaxing before the rush of Rome and the cruise stops to follow.

Suggestions would be appreciated regarding:
1) Itinerary (include or skip Bologna, Ravenna, Cinque Terre; other ideas)
2) Where to pick up and drop off a car
3) Towns to visit in Tuscany/Umbria (I’ve read RS and other recommendations but would enjoy hearing yours)
4) Where to base ourselves so that we can stay in only one or two places between Milan and Rome

Note: We are 69 and 72, active travelers, love beautiful scenery and visiting churches, and aren’t interested in wineries or shopping.

Thanks in advance for your help!

Posted by
876 posts

We are going to Bologna, Ravenna in May so I can't comment on that part yet! I would skip the CT since it takes a long time to get there and back. One option is to go from Milan to Florence by high speed train and spend the night in Florence on the 26th. You can pick up your rental car the next day in Florence (either at the airport or downtown) and then drive to a base town in Tuscany. Perhaps Pienza since it's a relatively flat, centrally located town? From Pienza, you can visit any number of towns in Tuscany and Umbria. Some of my favorites: San Gimignano, Volterra (can combine these two in one day) and Assissi and Cortona (another day trip). You should be able to drop your car in Orvieto and take the train into Rome from there.

Posted by
98 posts

Thanks for your suggestions. I hope you will write about your visit to Bologna and Ravenna. We may take a cruise out of Venice in the future and could visit those two places before or after the cruise. A friend who has traveled in Italy several times suggested that Florence would be a difficult place to drive from if we picked up the car there but I imagine it would be less complicated if we picked one up at the airport. Enjoy your travels!

Posted by
876 posts

On our last trip to Italy, we flew into Milan and spent a couple of nights in Varenna. We then took the train to Florence and took a taxi to the airport car rental facility to pick up the car. This was adjacent to the main highway heading to Siena so there was very easy access. If you go this route for a car, make sure you tell the taxi driver you are going to the car rental facility and NOT the airport itself.