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14 days in portugal/looking for suggestions

We will be spending 14 days in Portugal in June. First 4 nights we are in Azores and already booked lodging and have ideas of what to see, but always up for more info. After Azores we fly into Porto for 3 nights, plan to train to Lisbon for 2 nights then rent a car and drive from Lisbon to Algarve for 4 nights. The last day we will drive back to Lisbon to return car and fly back to Boston. Would love some tips on lodging (best areas to stay in each Porto/Lisbon/Algarve) as well as must sees and some off the beaten path/local flavor ideas. We are traveling with another couple and are open to hotels or air bnb's etc. We'd like to be in walking distance to some activities and somewhat close to train in Porto and Lisbon and in Algarve we will have a car so can stay anywhere, but up for suggestions. Would love to hear from people that have done this trip. We like mild hiking, biking, wine tasting, good food and live music and excursions. Like some general plans and direction without filling every minute of our days. Thanks in advance!!

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