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Time in Portugal

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I'm looking for advice on how to divide my 2 weeks in Portugal in October. I was thinking something like 6 nights Lisbon, 4 nights Madeira, and 3 nights Evora. But not sure considering the October weather in Madeira and the short amount of time. I mean, what are the odds it might rain all 4 days I'm there? Should I skip Madeira and hop around central Portugal for those 4 days instead, maybe add a night for Evora? I would love to see northern Portugal as well, but don't feel like I'll have the time this trip.

I love art and history. I like guided walks but not too big on group tours. Don't mind walking 8-10 miles/day (well, maybe not every day!) and will rent a car when not in Lisbon. I will be traveling by myself.

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