Portugal route - Oct '21 - So to N or N to So ??

I'm glad you're adding more time; there's lots to see in Portugal.

I'd definitely start in the north at that time of year--not that I travel to Europe that far off season myself. The north is typically quite rainy in October, and if I'm going to get wet, I'd rather the temperature be warmer rather than cooler.

Check public transportation to be sure you have decent options for day-trips from Sintra to Cascais. I know Sintra's closer to Cascais than to Lisbon, but that doesn't necessarily mean there's frequent transportation in that direction.

Check online for information about the weekly market in Guimaraes. I believe it still operates. I enjoyed it, though my visit was a very long time ago.

Agree that I would also start in the north. We have been to every town you mentioned. Regarding 10/28 through 11/1, I've looked at google.maps and the driving time from Tomar to Marvao is a bit over 1.5 hours; from Marvao to Elvas about 1.5; Elvas to Evora about 1 hour. Marvao is a very small hilltop village. The castle is nice and the views of the countryside are beautiful but you can probably see it all in two or three hours. You might be able to stop there for a couple of hours on the way to Elvas and sleep in Elvas. Elvas is larger but since it's only one hour to Evora you might be able to spend the afternoon and evening as well as a few hours in the morning before driving to Evora. We were there in late September, 2019 and it was very peaceful so if you're looking for some down time that would be the place to stay. One thing to consider is that there are few restaurants in Marvao and only two were open for dinner when we were there. There was a tiny grocery store where we bought eggs, meat, and bread for breakfast as we were in an apartment. Elvas is larger, with more to see and with many restaurants open when we were there in late September, 2016.

It's always hard to have to choose between towns. Good luck!

I agree with the other posters - start in the north.

A few thoughts. There is a lovely Quinta in Pinhao (Douro) you might want to check out. Quinta de la Rosa is right on the river, has a nice restaurant and is close to town. I was there in September (timed a quick trip between surges) and it was very nice. We took the train from Porto - very easy - and the Quinta gave me the name of a man who taxied us around the area. I preferred not to drive with the winding roads - and wanted to be able to drink the great wine.

Instead of Batalha for a home base in the ‘Silver Coast’ area, you might want to consider one of the towns along the coast. I stayed a week in São Martinho do Porto during my scouting trip before moving here and really liked it. From there, we did day trips to all the places you mentioned and it was a cute, beach town. I also stayed in a very new hotel between São Martinho and Foz last summer that was great. If you are interested, I can look up the details.

When you get back close to Lisbon, you might want to turn the car in in Cascais rather than the airport. The car rental agencies (at least Europcar and Hertz) are very close to the train station. There are a couple of buses that run frequently between Cascais and Sintra. And, both Cascais and Sintra have great train connections to Lisbon.

Hello
North to south is the best option weather wise.
If you want to splurge on accommodations you may consider Pousadas of Portugal which are old historically important buildings (monasteries, convents, palaces, castles) that have been converted into hotels.
https://www.pousadas.pt/en/hotels
The other option is Leading Hotels of the World.
https://www.lhw.com/property-search/Portugal#sortby=picks&musthave=&currency=&limit=10&timeseed=637460550545135600

You may also consider the Hop On Hop Off Yellow bus while visiting Porto, Lisbon, Coimbra, Guimaraes.
We use it because we don't have to worry about driving in the city, finding parking, etc, .
https://www.yellowbustours.com/en/porto

A little south of Coimbra we visited the Roman ruins of Conimbriga and found the mosaics interesting, maybe something you may want to see.
https://www.portugalvisitor.com/portugal-city-guides/conimbriga
Happy travels

Thanks to all of you for validating the North to South route.
Acraven: Thanks for the Cascais feedback. I did look at transport to/from Cascais.. It does seem a bit tricky - but we will ask the "locals" and if still a pain - will wander in other directions. Shouldn't be too hard to fill a day (or 3) in Sintra area.

Carol: re Marvao vs Elvas - I will look closer at the 2 - since it's a 1 night stop and drive distances are relatively short will probably go with the one with more unique landscape (?)

Kathryn: I'll definitely check on quintas in the Pinhao area. I see there are quite a few. Will hunt for something with a restaurant or close(er) to a town for evening meal. I will check out Sao Martino do Porto. I had picked Batahla kinda for it's central location, found an interesting hotel on the main plaza to the cathedral.
Since will be October wasn't certain of the weather at the shores (winds off the Atlantic etc). While we don't do beaches for sun we love the scenery and seafood. So may be a good change from hills, rocks and castles.

Allophone: Thanks for the thumbs-up for Conimbriga - I had it on the list as we drive South from Coimbra.
As I checked your links - I found a tab for self drive vacations - linked to Portuguese Trails. Fun to see that - I used them to set up our time for 2020 - was a last minute plan. I plan to use them (with a lot more input from me) for this next trip. They seemed very professional and had lots of good ideas for hotels/day tours etc. Might as well support some locals instead of booking.com.

Thank you all - any and all ideas will be welcome - since I have at least 9 more months to obsess.

By happenstance, I am sipping Ginjinha d'Obidos as I type - from the bar that Rick recommends - the only good reason to visit Obidos, but you can get good ginjinha most everywhere in the center (and you might not even like it that much). I think the reason most people like Obidos is because it's the only hill town they visit. I spent several days visiting hill towns (and not-hill towns) in eastern Portugal, from Monsaraz to Elvas 2N to Castelo Rodrigo 2N.

I agree with Carol that Marvao isn't worth more than a few hours. I saw everything listed in the RS book in Evora in less than a day, and enjoyed a cork factory tour as well. I loved Elvas, interesting sights, great views, pretty walled town and lots of restaurant choices.

I based in Tomar 3N to visit Alcobaca, Batalha, Obidos, and Nazare (wish I'd picked any other coastal town). There aren't many sights in Tomar but there are restaurants and a coin-op laundromat. In fact one of the best experiences I had was at a 15th century restaurant in the central plaza - pretty authentic atmosphere and the food was quite good (no tomatoes, potatoes, peppers or chocolate - they only came to Europe in the 16th century.

I spent 2 nights at Quinta de Marrocos right on the Douro, just outside Regua - wonderful. Great table wines and excellent port and delicIous meals, lovely furnishings in the rooms, like staying at your grandmother's.

If you aren't spending a night in Cascais, don't drop the car there - remember you'll have all your luggage with you! I would drop it (the car, not the luggage) at the airport (easier than driving into Lisbon - ugh) and take Uber or a taxi to Sintra. They aren't expensive and the trip is about the same from the city center and the airport. Any other way to Sintra is a pain in the butt and will take 2or 3 times as long. And presumably the car rental places are in the new part of the city. The walk from the train station to the old city center is only 10-15 minutes, but it is almost all cobblestones so it's difficult with rolling luggage and will take longer. So you'll want a taxi for the last part anyway. I took the bus to Cascais on the long route for a stop at Boca do Inferno - not really worth stopping for - and it doubled the travel time not including the long wait for the next bus (it was late arriving). The direct bus takes at least 40 minutes and I ended up taking Uber back because I missed the last bus. Uber was great.

I highly recommend to stay in Cascais rather than Sintra. Cascais is just beautiful, easy walking and walking.....can take a bus trip to Sintra....and we definitely recommend a stop at Cabo da Roca, the westernmost point of Europe mainland....between Sintra and Cascais. We stayed at the Pergola Guest House B&B....so charming....amazing breakfasts....the staff is excellent. 3 weeks in Portugal and we would definitely return to Cascais.

Coimbra is a very good base. We enjoyed our stay at historic Quinta de las Lagrimas.

Thanks to all of you! I'm really hoping this will come about this year. If not - well the brain work will have been done.
I will check on all your ideas - and may even have to add a bit more time. It's grand to be retired and have the funds (tho some what limited) to spend as much time as we like exploring.

When in Porto, don't forget to visit the stunning Bom Jesus de Braga! It's absolutely (and literally) breathtaking to ascend those beautiful Baroque zic zac steps. A commuter train takes you from Porto's main station to Braga, from where you have to take a bus to Bom Jesus.

Oh, while in Coimbra, make sure you book tickets to the University library in advance and enjoy a show of Fado de Coimbra (there's a free one at Café Santa Cruz at 6pm), which is very different from other forms of fado in the rest of Portugal.

Along the Douro, add a stop at Lamego to see Santuário de Nossa Senhora dos Remédios. It's quite similar to Bom Jesus de Braga, but no less stunning. I found these places scenic and refreshing because you probably won't see dumb, rude, and loud tour groups in these less explored areas.

Fazer boa viagem!

We did a wonderful week long Douro River cruise. It was pricey and if you don't want to do that, consider taking the train upriver from Porto. The railroad runs on the north side of the river. You could enjoy the scenic views without having to drive. If you drive, you will not necessarily be on a highway down in the valley.

For Porto, we found the very, very best B&B EVER. It is the In Patio Guesthouse. It only has five rooms, so book early.

I will check the Inn Patio GH again. When last I looked it was either booked or not taking reservations this far in advance.

We will have a car after Porto - I know a river cruise would be fun - but would rather put the $$ in more "land" time and different experiences. At least on this trip.
More to come on the journey planning. I may try to add several weeks at each end (Spain - Northern/coastal & then Andalusia).