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Portugal - Where to go, stay, eat

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My boyfriend and I have just booked a trip to Portugal from October 6th-19th. We arrive in Porto and depart from Lisbon. We have booked a rental car for 8 days and would love to do a circuit of the country, allowing one full day or two full days in each town/city as required.
My dad is portuguese, and for me this trip is really important and meaningful. I'm the type of traveller where I need to experience the food to really understand the culture. I love sight seeing etc. But this will be my first Europe trip (we are both from and live in Canada).

Any help on where to go, what to see and any recommendations on food would be really appreciated.

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