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12 nights in Portugal - need help with itinerary:)

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Hello my husband and I are going to Portugal for 11 days/12 nights next Fall for the first time. We love hiking, little old villages, castles, beautiful coastline and meeting the locals. We prefer historical sites that are outdoors to museums and dining al fresco at little family run places to fancy restaurants and prefer a small place with live local music to the Dance/Club scene. We will rent a car once we leave Lisbon and will split our stays between guest houses and pousadas and/or apartments. We hope to spend under $150/night for accommodation but will spurge on a pousada. We are going to forgo the Algarve and Alentejo on this trip so we can focus in on the areas between Lisbon, Porto and the Douro Valley. Here are my initial thoughts on itinerary and I would appreciate any suggestions on towns and accommodations and timing of our stays (such as spend more time here and less time there):
Nights 1,2 -- Lisbon, arrive late in pm; see Lisbon sites
Nights 3, 4, 5 - Stay in one of these towns to see all (we will have car) Sintra, Cascais & Estoril
Night 6 -- Obidos or Nazare to explore these towns and coastline
Nights 7, 8 - Porto or Vila Nova de Gaia to explore these towns
Nights 9, 10, 11 - Peso da Regua or some other town along Douro river so we can hike, kayak, wine taste and explore little villages from a riverside base
Night 12 - Lisbon (very early flight in am)
Thank you:)
Jennifer from California

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