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Driving Itinerary

Sadly, I beginning to plan a trip that perhaps will be my last visit to Italy:( We have done the Po Valley region, South and Sicily, I am now looking at the heart of Italy. We prefer public transportation but I am thinking of a driving side trip. I would love ideas of small towns or interesting sights (we love history) we might find along the way. I am thinking of a bus from Florence to Siena, renting a car and driving to Assisi on to San Marino and then returning the car in Bologna, perhaps a side trip to Ravenna. To avoid crowds I am thinking of a late March or early April trip. Though I object to 1 night stays we might require some here. Time between most locations, are 2 hours. Could we arrive early in one spot and head out to the next stop for the night? Where would you recommended more or less time or not at all?
My first thoughts are
Fly to Florence 4 nights
Road trip minimum 5 nights
Bologna - 4 nights side trips to Parma and Modera?
Milan - 2 nights
Fly home

Of course then there is my other thought, no road trip but Florence, Milan and the Italian lakes...but April in the lakes?
Love any and all thoughts, I have 11 months!

Posted by
1817 posts

To avoid crowds I am thinking of a late March or early April trip.

Sounds like a lovely trip! Just so you're aware, Easter 2027 is March 27th. So many Europeans will be on holiday from Good Friday, March 25th through the following weekend. Personally, I wouldn't go near Assisi over Easter. Or spend the night there, not my fav, just too many people, but others will disagree. We loved Siena, I had to look up the recent TR about it here. https://community.ricksteves.com/travel-forum/trip-reports/may-2026-trip-report-italy-part-1-siena.

Posted by
3722 posts

Some thoughts
Why San Marino?

I think you are giving Ravenna short shrift. It has numerous sites with stunning mosaics, in addition to being a lovely town in and of itself. It oozes history. For example, it was the capital of the western Roman Empire in the 5th century. It needs 2 full days.
My guess is that the weather in April might be iffy in the lakes.

Posted by
10055 posts

If you rent a car, don't speed, they have speed cameras everywhere. Also, take care not to enter cities or towns where there are restrictions. There are frequently many places with zones limited only to residents.

Tickets are expensive.

Consider taking day tours or bus or train.
Assisi is great, as are Spoleto, Gubbio, Perugia and Orvieto.
Ravenna is good for a day trip.

Posted by
576 posts

I would spend more time in Milan and less time in Bologna. Milan has several great attractions, including the Duomo, Pinacoteca di Brera, Pinacoteca Ambrosiana, Sforza Castle, and San Maurizio al Monastero Maggiore. In my opinion, two days is not enough. With that said, going inside the Duomo and up to the roof are not must-sees.

Regarding Ravenna, if you’re interested in mosaics, it deserves two days. If you’re not interested in mosaics, Ravenna is skippable.