I hate to have to say this as I live in Lagos in the South, but now that I see that you want culture, history and off the beaten track, I am going to recommend that you should be heading north of Lisbon after Evora.
Much of the history of Portugal lies there in places like Setubal, Obidos, Batalha, Coimbra, Porto, Nazare, Lamego, Guimarães, Bragança etc.
The Counts of Lusitania originated in the North. The South, particularly the Algarve, were frontier areas. Indeed, the Kings of Portugal up to Manuel in 1907 were known as the "Rei do Portugal e o Algarve" - "The King of Portugal and the Algarve". The Algarve always has been a "colony".
However, if you are coming South, I recommend the following route :
- Lisbon
- Evora
- Alcacer do Sal (See the castle)
- Setubal (See Setubal and Palmela Castle)
- Cross the Sado Estuary on the ferry at Setubal to the Troia Peninsula and make your way South to Santiago da Cacem and Sines.
- From Sines wander down to Vila Nova Milfontes.
- From the latter head in the direction of Aljezur diverting a little to have coffee in the town of Odemira - Agricultural centre nestled in a lovely little valley.
- From there head to Odeceixe -
- Then Aljezur
- From Aljezur head to Lagos and base yourselves here.
- From Lagos explore
- Sagres & Cape St. Vincent (35 kms.)
- Tavira - (100kms)
- Monchique - (20 kms)
