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Driving the Bernina Pass vs. Bernina Express

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We are planning a trip to Italy, late Sept. or early Oct. and thought we’d detour into Switzerland for a few days. I’m thinking of flying into Milan and driving to either Lugano or Varenna and staying for two or three nights. From there I’d like to drive to Pontresina and stay for 3 nights doing day trips from Pontresina. My questions:

1. I have read a lot about the Bernina Express and I was wondering if the route is driveable. How scary are the roads? (We have driven all over Europe and used to drive on mountain roads, but although my husband is game for any drive, I’m a little fearful of the narrow roads with no guard rails. He would be doing the driving.)

2. What would be a recommended first stop (2 to 3 days) after we land in Milan? I think we would like to stay at one of the lakes and was thinking of Lugano or Varenna..

3. Fodorites seem to like Pontresina as a base for the Engadin region. Any opinions on this and/or hotel and restaurant recs?

4. What is the weather generally like at that time of the year?

Thanks for any advice and info.

Barb

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