With 2 weeks, I'd suggest from Cascais:
Start in Evora (cork factory, megaliths, cathedral), then east and north to the hill towns: Elvas, Monsaraz, Vila Vicosa, Castelo de Vide, Marvao, Belmonte, Guarda, Castelo Rodrigo (don't miss the rock art, best on a night tour), then west into the Douro valley, small towns around Porto, Guimaraes, Braga, Aveiro (though Porto is lovely and it'd be a shame not to spend a day or two there), then south Coimbra, Viseu, Tomar, Alcobaca, Batalha, a coastal fishing village and drop the car in Lisbon.
Some of the places I list are just stops along the way from place to place. The Douro valley has some picturesque hiking and lovely quintas to stay in.
The RS guide is good for the western part of Portugal. Lonely Planet was very useful for the whole country. One caveat - driving times are often as much as 50% more than GPS/Google estimates when you're not on the main roads in the west.