Italy

How many nights are you spending in each of these places? What time of year?

Taking Bernina express to Lugano. Train from Lugano to Bolzano. Pick up car in Bolzano3 nights in San Candido then 2 nights in Oberammergau then drive to Bolzano and drop off car. Then looking to do something else. Would be Sept 2020

I know I am repeating myself, but Bernina Express does not go to Lugano. How are you going from St. Moritz to Lugano?

The Bernina Express runs a bus on the Tirano - Lugano segment. This may be new-ish. When I made the trip I took the Postbus Palm Express.

https://www.rhb.ch/en/panoramic-trains/bernina-express#info

(See section on Lines)

Bernina Express Bus
The panoramic bus operates on the following route:
Lugano - Tirano - Lugano

Edit: I'm finding references to the Bernina Express bus from 7 years ago, so apparently not that new.

The route isn't logical, you loop back on yourself.
You should go from
- Milan to Lugano by train
- Lugano to Tirano by bus (don't stay in Tirano)
- Tirano to St Moritz area by Bernina Railway
- St Moritz to Oberammergau by train to Scuol, bus to Landeck-Zams, train to Innsbruck, then Garmisch-Partenkirchen and Oberammergau (long journey, over seven hours)
- Oberammergau to Bolzano by train via Garmisch-Partenkirchen and Innsbruck

Back to the first question. There's lots to see and do between Bolzano and Rome. What are your interests? Have you been to Italy before? Do you plan to keep the car and visit more rural areas (Italian towns are not car-friendly) or drop the car and travel by train to Rome?

Thank you all for your great suggestions. Glad it’s a year away to have time to re think. As far as extra days. We plan to bring the car back to Bolzano and take the train to Rome. We have been to Rome and Venice twice. Although plenty to see we would like to visit other areas of interest.

Bologna is good for day trips. Some folks really like the town itself (like me), others not much, if at all. Like it or not, it's a convenient place to stay since it's a major rail hub (chances are you'll go through it on your way south) and it has good restaurants. You can day trip to Ferrara, Modena, Padua, and more, even Ravenna though it's a tad farther.

Maybe Assisi for 1N, then Orvieto 2N. There are frequent fast trains from Orvieto to Rome. Florence 3N if you haven't been there.

All great ideas. Love this site and thanks for your help

September is magnificent in the mountains. You could spend your three nights in the Val Gardena or the Alpe di Siusi, less than an hour from Bolzano with terrific hiking and natural beauty,

No itinerary advice but used to live in Garmisch-Partenkirchen and loved visiting Oberammergau. That entire area of Bavaria is amazing :)

Thanks for all the help. As a result we have changed our direction.
Now we will fly into Munich, rent a car and drive to Oberammagau. We still want to do the Bernina Express but because of the cost want to drop the car off in Germany as close as possible to the border and take a train to St Moritz. Any suggestions which town is best? Would it be Landau although I think a train would still take 5 hours?

The seat61 website suggests a way to take the Bernina Express on the cheap. It may be helpful to you. You'll need to scroll nearly halfway down that webpage.