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Trip planning 19 nights recommendations

Greeting friends
Traveling to Milan airport and out of Rome airport from September 25-October 14
Have been to Italy a few times and visited Milan and Bologna and Rome on trips in the past .
This time we decided to rent a car for our trip. We enjoyed driving last year in Portugal and enjoyed the flexibility and adventure. I understand the ZTL zones and speed cameras are strictly enforced in Italy and will be vigilant to that while traveling.

We want to go to the small country of San Marino or area around San Marino a few more days would be better but rooms are tight the days we have available.

I am also looking for ideas where to stop for 5 nights between Bergamo and San Marino.i was thinking Parma or Mantua possibly Ferrara or some other idea with nice city center. Trying to keep drives between stops 2-3 hours

Here is my plan
Bergamo Città Alta September 25-29
Unknown stop between Bergamo and San Marino September 29-4
San Marino proper October 4-6
Orvieto October 6-9 drop car train to Rome
Rome October 9-14 piazza Navona area

Thank you. For any ideas

Posted by
8923 posts

Been to San Marino, not much to see there, frankly, I recommend skipping.

Renting a car is a serious liability in big cities, also parking is a royal pain even in smaller cities.

Recommend Ravenna as well as many great places in Tuscany and Umbria.
Siena is special, need two days there. Cortona and San Giminacino (sp) are great in Tuscany. In Umbria, Assisi, Gubbio, Spoleto, Perugia and Orvieto.

Posted by
11990 posts

Modena would make a nice base for Emilia-Romagna for 5 nights. The great Ferrari museum in nearby Maranello is worthwhile, food tours abound (parmigiano reggiano, prosciutto, balsamico), daytrips to Parma, Modena, Bologna, Ferrara.

We have not been to San Marino but many friends have and have said it was barely worth a day trip and only if the weather is clear so you can see the view. Nearby Ravenna is lovely and would make a good choice for a few nights and you can easily go to San Marino if conditions are right.

Posted by
189 posts

Thanks for the replies. I have been using chat gpt and it seems to really crunch a lot of web resources to give pretty clear results. I am just not sure if it’s always accurate. Parma seems a good option for a few days stop. Good areas to explore