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Help with Portugal trip in the fall

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I'm thinking of a 1 week Portugal vacation this fall. I can book non-stop flight to Lisbon with my FF miles. My travel timeframe is late September through early November. I was wondering how is the weather during that timeframe (I'm mostly concerned about rain). Is there much difference between late September and early November?

Also, we would spend a 7 nights there (could maybe squeeze in 1 more if it makes more sense). How should we plan that itinerary as far as nights in Lisbon, and possibly renting a car to see other parts of the country? What would make the most sense given the time of year and the length of our visit? Is there a possible open-jaw scenario that would work better then RT to Lisbon (from NYC)?

We are city people (live in NYC, also loved Barcelona, Rome, etc) but do enjoy scenic trips as well (like California or Almalfi coast, also Tuscany) and smaller towns (like Orvieto, Toledo) .

Thanks.

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