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Three nights in Braga or Guimares?

I would like to spend some time north of Porto during a one-month trip to Portugal. After Porto, and before two nights in Pinhao, which location makes more sense?

Also Between Pinhao and before Tomar I was thinking of staying near Monsanto for one night. Is there a different place that would make a good picturesque, historic one nighter?

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Braga and Guimarães have a different feel.
Braga is a bigger city and would be my choice, it has better public transit but if you're driving that's a moot point.

Monsanto is a good choice for what you're looking for, my other suggestion would be to look at Aldeias do Xisto they are closer to your travels to Tomar ( depending on your itinerary you'll probably drive by them on your way to Monsanto).