Dolomites in September

So you are going to rent a car in Italy and drop it in Prague? That is going to be expensive as the car will then have to be transported back to Italy, and you will have to pay for that as well as loss of days that it is not available to be rented. Also the rental company may not want their cars travelling to Czechia.

Better do some more homework on this as there is more than just a choice between Milan and Venice.

PS, You might consider renting the car and dropping it in Bolzano, then taking a train to Prague. It is about a 10 hour journey and there are a few single connection itineraries, changing trains in Vienna or Munich.

Last Sept we went to Ortisei and flew to Munich since it was direct. Spent a few nites there and then took the train to Bolzano and the bus up to Ortisei. Note that some roads in the region are closed to cars from 9-5 so that might impact how useful a car will be. The bus system in the region is extensive and pretty frequent (hourly or better). We were fine just getting around by bus. You can look up schedules online if you've figured out where you're planning to visit in the Dolomites. Most hotels include a transit pass with your stay so the buses are free, including down to Bolzano. So depending on your plans for the Dolomites it may be easier to just pick up your car before your drive to Prague. Be sure to check into drop-off fees since many rental agencies have a significant charge if you drop a car off in another country.

I think Munich is the best place to fly into for the Dolomites. Rent your car in Germany and return in Germany before heading to Prague.

We have used www.gemut.com for our rental cars in Germany and driven to the Dolomites and back. Many times.

Paul is spot on. We never used our car once we arrived in Ortisei. There is enough to do in the Val Gardena area for a week easy. You can also go further east for a couple of days in Corvara or San Cassiano by private car or taxi easily arranged through your hotel.

Flights from the US are usually cheaper into Munich and Milan. I would fly into one and out of the other for the trip to Prague. Milan is flight prices to Prague are cheap. Munich if you train to Prague. Renting a car just doesn’t make sense for this trip.

I will add that people I know who live in the Dolomites region usually fly out of Munich when going to the USA as it has direct flights to more US cities than either Milan or Venice.

Agree with Paul about renting car/returning car in Munich, then you could train to Prague after dropping off car. Stayed 6 nights in Castelrotto last summer (flew into/out of MUC) and enjoyed having a car to reach hikes in different areas of the Dolomites. We drove up to Compatsch parking lot for Alpe di Suisi hiking around 7:30-8am to reach trailheads before the road is closed to traffic.