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Road trip Milan to Portugal

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My partner and I are leasing a compact 4x4 and taking a month to drive from Milan to Portugal from 20 Sep - 22 Oct.

The general plan is to spend the first 3 days based in Milan to get over jet lag from Australia and explore the area, then head up to Lake Como and Swiss Alps for a few days. Any recommendations on great little villas on the lake or in the alps? Places to eat?
Then we were thinking we'd drive down to the south of france for a week, Spain for a week, Portugal for a week, then leave the car there and fly back to Milan for our return flight home.

In your experience, do you think we are trying to cover too much ground? What are the best spots that we absolutely shouldn't miss? Any recommendations on places to stay and things to do?
We are in our mid-twenties and aren't that interested in touristy sightseeing. We would really like to see some beautiful countryside and beaches, interesting little villages and absorb the culture, eat amazing food, nightlife and drink local wine etc, as neither of us have done that part of Europe.

Would love all suggestions including any special events (festivals, sporting, cultural, arts music etc) that might be on during that time.

Also will it still be warm enough to swim or surf in Portugal?

Thanks so much in advance.

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