9 nights between Lisbon and Porto, help please!

We preferred Evora to Obidos. Obidos exists for tourism, is a pretty village, two hours at most to see it all. Evora has a Roman Temple of Diana. There is a very nice Pousada there. Skip Caiscais, a beach resort. Make sure to visit Belem area of Lisbon and the Jeronimos Monastery. Gulbenkian Museum is a also a treasure in Lisbon.
Since you are traveling with older adults, to avoid hills, stay in the flat area near Rossio and Restauradoures Squares in Lisbon. Hotels there are Sofitel and Avenida Palace. There are less expensive hotels nearby as well. You can take the Elevador up to Barrio Alto, good restaurants. In Porto, it is flat near the riverfront.
It is easy to visit Sintra by train from Rossio Station.
You are correct that Guimares and Braga would be interesting places to visit.
Next trip!
Guimares was the first capital of Portugal.

Given your time constraints, this looks pretty good. I agree that Obidos might not the best use of your time due to the crowds. It looks as though you might be stopping in Coimbra, which I recommend. It’s a lovely city with lots of history. However, the university (one of the big draws) is up a pretty steep hill. So, you might want to look for transport up to it.
And, yes, Lisbon is hilly and will be challenging for some of your group. There are elevators around town and ways to get part way up the hills to Alfama, Chiado and Barrio Alto

Good plan. By the way, we found our most favorite B&B ever in Porto. It is the In Patio Guesthouse. It is at a great location with wonderful hosts. It is spacious and newly refurbished. Fantastic breakfasts!
Only five rooms, so book early.

Thank you Suki and Kathrvni!
Lots of good advice! I've yet to get to the details of what exactly to see each day, but defintely some of the Lisbon museums are on the list: Gubenkian, tile, horse-carriages for sure. And probably on the first day do the Belem area with the tower and the monastery. It looks flatter than the rest of the city, so it might be a good way to start our Lisbon visit.

I'll take a closer look at Evora vs Obidos. Obidos was on the way from /to Porto, so looked like a logical choice and the pictures look super cute but as I keep seeing it's very touristy and crowded apparently, so I am not sure if we are going to change that to something else.

We'll for sure do the LIbrary and the university in Coimbra. Thanks for the heads up that going up is a hassle. Perhaps, I should invistigate and see whether taxis can be used to get there (as well as other locations for our 8 days in Portugal). I really had no idea most of Portugal (at leas the areas I am looking at) are so hilly! Well, no way of making it flat to suit us ;)) so just have to find a way to deal with this.

geovagriffith, thanks for suggestion, but we won't be using B&Bs this time.

Greetings!

Greetings!

I am trying to get open-jaw tickets so that we can fly into either Lisbon or Porto. Looking at mid-September.

So, my question is -- Would you start with Lisbon and finish in Porto or start in Porto and finish in Lisbon? And would you trade a day in Porto for an overnight stay in Coimbra.

I think I read somewhere that it's preferable to save the best for last. I guess the first few days people are sluggish and jet-legged etc, etc. So for example, when we go to Russia, I always do Moscow first and St. Petersburg last. I am not sure whether it'd be better to start in Lisbon or Porto (I hope I am not offending anyone from these cities ;))

I'm kind of leaning toward starting in Porto.

either Option 1
3 nights in Porto (which is really only 2 full days in the area)
1 nigth in Coimbra
5 nights in Lisbon

or Option 2
4 nights in Porto
5 nights in Lisbon

If I add 1 night in Coimbra....then:
day 1/ 22.30h arrival / check in around midnight (3 nights in Porto)
day 2 / full day in Porto
day 3 / Duoro Valley full day tour
day 4 / check out > transfer to Coimbra, University and city tour (overnight in Coimbra)
day 5 / check out > transfer to Lisbon with stops along the way: Batalha monastery, Obidos, Mafra Palace perhaps.. haven't decided yet (Lisbon 5 nights)
day 6 / Lisbon + dinner w/ Fado
day 7 / Sintra day trip
day 8 / Evora day trip (with seafood dinner in Sesimbra？see reviews that it's worth the stop)
day 9 / Lisbon + farewell dinner
day 10 / depart 10 am

I am getting a feeling that I've shorthanded myself on Porto. Our first day is going to be slow and how much can we see in a day. Also, due to the jetlag ..having Port wine tasting ...hm... It feels like we'll do a couple of churches, the bridge, the wine caves...and that's about it if I am being realistic. Also, we eat kind of slowly, so that means at least 90min for lunch and 2.-2.5 hours for dinner. So I wonder, whether I should go with option 2 by skipping an overnight stay in Combra and just doing the University (Royal Palace + Chapel of St. Michael + Joanine Library) and moving on to Lisbon via another stop along the way.

Option 2
day 1/ 22.30h arrival in Porto / check in around midnight (４ nights in Porto)
day 2 / full day in Porto
day 3 / Duoro valley full day tour
day 4 / Full day in Porto
day 5 / check out > transfer to Lisbon via Coimbra University with possibly one or two stops along the way: Batalha monastery, Obidos, Mafra Palace...? (Lisbon 5 nights)
day 6 / Lisbon + dinner w/ Fado
day 7 / Sintra day trip
day 8 / Evora day trip (with dinner in Sesimbra)
day 9 / Lisbon + farewell dinner
day 10 / depart 10 am from Lisbon

I know it's very busy. But we are Japanese )). This is quite leisurely by Japanese standards. In 8 days Japanese tours usually visit the whole of Spain + Portugal :))

Would appreciate your feedback / advice! By the way, the reverse is also possible. Starting in Lisbon and finishing in Porto.

Thank you,

Anna