There is so much history on the route you have outlined that books have been written about it.
From prehistoric times when men erected dolmens and worshipped the setting sun near Sagres, through the eviction of the Moors, the Portuguese Voyages of discovery to the Napoleonic Wars when Wellington erected the Lines of Torre Vedras north of Sintra your route will take you through such a wealth of History that it is impossible to recommend one and not the other.
However, here is a list you could start with:
On entering Portugal at Ayamonte from Spain:
Castro Marim - Medieval Castle
Tavira - Founded by the Romans and now traditional Portuguese coastal town.
Faro - See the old town
Lagos - Where I live! See the following link for a synopsis I have just written on this area
http://barlaventostravelblog.blogspot.com/2007/07/must-see-do-around-lagos.html
Going North:
Alcacer da Sal - Battle and Fortress
Setubal - Setubal and Palmela Castle
Lisbon - at a minimum
- Castelo São Jorge
Find the Chapitu Restaurant near by and sit on its terrace having lunch and enjoy the view over the Tejo
see:
http://barlaventostravelblog.blogspot.com/2007/06/lisbon-restaurants-with-views.html
(This is on my blog. If you don't get the full url just go to my blog - details below and search for chapitu.)
- Belem Monument
- Jeronimos Monastery
- Palacio - Queluz
Sintra - Pena Castle
Heading North -
Obidos - Old walled city
Batalha - Cathedral
Alcobaça - Monastery
Fatima - Catholic Sanctuary
Coimbra - one of the oldest Universities in Europe
Nazare - Old traditional Fishing Town
Porto - 2nd City of Portugal, Potr Wine, Douro Valley
Have a browse of my blog where you may find other posts of note:
http://barlaventostravelblog.blogspot.com
If you are genuinely interested in Portuguese History get hold of the following book:
Portugal - A Companion History by Dr. José Hermano Saraiva. (In English) - ISBN 1 85754 211 8
This a short but very good overview of Portuguese History by a gentleman, although now in his late 80's continues to present weekly history programmes on Portuguese T.V. on some esoteric aspect of Portuguese History.
Enjoy youself
