So after refining and focussing on our time and inclinations (history, culture, food, memorable locations, art) here is my proposed itinerary: ( this is locations, food and tours and activities will be filled in )
6 nights in Lisbon (arrival city)
4 nights in Coimbra, with day trips to Conimbriga, Aveiro, possibly schist village.
4 nights in Porto.
rent a car.
4 nights in Braga, with day trips to Viana do Castelo, Ponte de Lima, Guimaraes.
3 nights in Tomar, day trip to Batalha, Nazare or Leira
1 night in Elvas, see Marvao on the way.
4 nights in Evora; see Estremoz on the way. Day trips to Arraiolos, Monsaraz, Cork forests, megalithic stones.
3 nights in Obidos, day trips to the Silver Coast (to avoid the day trippers in Obidos) including Sao Martinho do Porto, Peniche, Caidas da Rainha.
drive to Lisbon airport drop off the car, and then
2 nights in Sintra. Taxi to the airport.
I am leaving out the Algarve completely on this trip. I am an optimist though. If I love it I will be back, and maybe visit the Algarve then.
Thanks in advance!