Car rental pick up in Bolzano italy and drop off in St Moritz Switzerland

Try the three consolidators: AutoEurope, Kemwel and Gemut.

However, there is usually a horrendous drop charge for dropping the car in a different country. Can you not figure out a way to use the car in just one country?

Call Autoeurope, if you have a toll free number, or go to the website. You will pay a cross-border fee of up to 1,000E, as the car will be returned to Italy, probably on a truck.

Easy solution, train Bolzano to Oberammergau, then train to St Moritz.
www.bahn.com for schedules.

The trains are so easy and inexpensive compared to renting a car. Plus, it is more relaxing! Unless you have a lot of luggage and unlimited funds, trains are the answer.

If you are intent on renting a car, you could drive from St Moritz to Como via Bernina pass, enjoying scenery similar to Bernina Railway, and hop on a train from Como to Lugano.
But train all the way is better, I agree with the comments above.

Thank you all for your comments. I guess a car is out. We love the trains but 8 hours and 4 stops seems quite long. I wonder if you can help if I add my itinerary to see if we should plan better?

Fly into Milan
Day 1-3stay in San Candido
Day 4-5 stay in Oberammergau
Day 6-7 take Bernina Express 2 nt pkg.
Day 8 train from Lugano to Rome to get on ship

In some cases Getting to all the places by train takes up to eight hours. I’ll take any suggestions to make this more smoothly.

Yes, but that 8 1/2 hour train trip from Oberammergau to St Moritz can have some very nice scenery as well, especially Chur to St Moritz on the Albula Railway with the famous Landwasser Viaduct along the way.

We will definitely take the train(s). So going from Italy to Germany to Switzerland and back to Italy, is there a train pass we should consider or should we just take individual country trains? Thank you again for your comments

There is a shortcut on the Oberammergau to St Moritz journey. You can go from Oberammergau to Innsbruck via Garmisch-Partenkirchen, then, from Innsbruck, instead of staying on the train until Switzerland you get off at Landeck-Zams and take a bus to Scuol, Switzerland, where it's a short train ride to St Moritz. This journey can be done in less than 7 hours instead of 8.5. BUT you miss the Albula railway and its famous Landwasser viaduct.

Check the SBB journey planner to find this route

There is an obvious reply, hire the car in Bolzano, drive to Oberammergau and all the other places, drive the Bernina (the landscape is the same of the train) and return the car in Como, finally taking a train to Lugano. This way you return the car in the same country where you hired it. The plan works better in summer; in winter Swiss will try to keep the Bernina road free from snow as much as possible but at some times it may be closed.

However, all such plans should better carefully checked on a map. All the places named in this thread look deceptively close, but trains and roads in the Alps are very slow, so they aren't close at all. Train links are slow and bound to main valleys only, but road itineraries are not significatively faster. For example, Oberammergau to St. Moritz by train may be 8 hours with several changes, the road itinerary is much shorter but we are still talking about 5 hours driving in real life (a section of the Inn valley road is quite narrow, I am glad I drove it once twenty years ago but I am not eager to drive it again). Also, the Bernina itinerary, be it by road or rail, does not end in Lugano but in Tirano, north of Como lake. The shortest itineraries between St. Moritz and Lugano are not through the Bernina, and there is not a straight rail link.