33 nights in Portugal

Can't respond exactly as you ask because I chose not to visit many of the places on your list. Here's what I did instead (May '26). 16 days on the ground, including travel days. I used public transportation only. My bases were Lisbon (4 days), Coimbra (2 days), Porto (2 days), and Braga (3 days). I don't count travel days. I did day trips to Santarem, Evora, Tomar, Aveiro, and Guimaraes.

Thanks. Where did you do those day trips from? I've read a little bit about Braga and Aveiro and have heard of the other places you mentioned. Did you like those day trips? Did you do them on your own or group tours? Anyway, thanks... this is helpful.

Lisbon > Santarém and Évora
Coimbra > Tomar
Porto > Aveiro
Braga > Guimaraes

Art museums, churches, and photo ops are the reasons I pick places to visit. Santarém, Évora, Tomar, and Guimarães all have churches/cathedrals that I wanted to see. In Aveiro, I was interested in photographing the moliceiros boats. I avoid group tours like the plague! I find them too restricting. I have to say, and others may vehemently disagree, but I didn't find Portugal as visually interesting as Italy or Spain. However, the people are lovely, and it's more affordable than the other two and less crowded. Don't get me wrong, combined with the sites in Lisbon, Coimbra, Porto, and Braga, I had a very enjoyable trip. Hope this helps.

Lisbon needs a minimum of 3 or 4 nights just to see Lisbon.
Sintra can be visited from Lisbon. It’s only 45 min by train from the Rossio station. So to avoid too many transfers you could base your self in Lisbon for longer.
From Lisbon you can take also a day trip (or more) to Cascais. Another day trip from Lisbon can be Setubal (Train) another one to Sesimbra (bus or Uber, about 45 min). Both have a nice beach, so you can stay a couple of nights too in either, since you go in June. Just be aware that the ocean water in Portugal is cold. Nowhere as cold as Baker’s beach or anywhere in the Pacific in California, but it is not Florida or the Caribbean or the Mediterranean (which nowadays with global warming is as warm as Florida). Uber in Portugal is super cheap, so don’t be afraid to use it.
Obidos can also be a day trip from Lisbon. Go to Campo Grande and take a bus with the bus company Rodoviaria do Oeste. I think I paid for the ticket on board, but don’t recall now. It’s just over one hour bus ride.
Evora is not far. The train takes about 90 min (that’s what I used) and there is also a bus. I spent 3 nights but you can do with 2 only. One full day is enough to see it.
Coimbra needs a day. However it is not super close to Lisbon, so you might make it a couple of nights. You might even consider staying an extra night and take a day trip by train to Aveiro.
Porto deserves 3 or more nights. It’s really gorgeous and I like it even more than Lisbon. You could even prolong your stay and take a day trip to Pinhāo on the Douro Valley and come back on the same day. I stayed a couple of nights (or was it 3?) in Pinhāo at a winery, if you have the time. I used the train then taxi to the winery. If you go to Pinhāo to stay and need the taxi number I’ll give it to you. There are only a couple of taxi drivers in town. One young who speaks English, one older who speaks only Portuguese, that I really struggled to understand (my Portuguese is poor) and even my Brazilian brother in law who lives in Lisbon had a hard time understanding. But he was cheaper than the younger guy. I have not had a chance to go south to the Algarve or to Nazaré yet, in my 4 trips in two years, so I will let others speak.

My trip was 23 days and I had a car for part of it.

Sintra. I went directly from the airport. What I wish I had done was take an uber or taxi straight to the hotel. I wasted a lot of time and energy taking public transport and then a taxi from the Sintra train station. I had 2 full days and felt that was enough.

Lisbon. I had 2 full and 2 more-than-half days. I could have spent another full day probably.

Evora. I was there for 2 nights. I was not overly impressed with the town. I drove to a nearby cork farm/factory for a tour and enjoyed it a great deal. One of the big attractions is the megoliths which for me are just big rocks, so I skipped them.

Tomar. Another town I thought was just okay. I used it as a base for day trips by car to the nearby monasteries of Alcobaca and Batalha which I enjoyed a lot. The highlight of my stay in Tomar was dinner at the medieval Taverna Antiqua.

Nazare. I spent an afternoon on the seashore. It was windy and the sand was blowing. The shops and cafes were very touristy.

Obidos. I spent 4-5 hours and it was enough. I was very glad I went. It would probably be a good place for 1-2 nights, to enjoy it in the early mornings and evenings without the myriad daytrippers.

Coimbra. I had 2 nights and would have liked more.

Porto. 3 nights and would have liked 1-2 more. Even more if you plan to day trip to nearby towns.

Pinhao. I stayed in a Quinta close to Regua. The Douro Valley is lovely and staying in a Quinta and learning about (and tasting) wine making and port was great. Others at the Quinta enjoyed hiking, I didn't have time.

I didn't visit the other places you listed.

Thanks to all... VERY helpful in giving me an idea of how many nights for each place. I've gotten it down to 10 nights left to divide between Tomar, Nazare, Pinhao and Porto. Any thoughts?