So much to do but confused with my itinerary, help!

I totally understand wanting to see as much as possible during your time in Portugal, but IMO you have way too much on this itinerary to comfortably do in two weeks.
With only four days in Lisbon, I’m not understanding why you would do three day trips. Four days for Lisbon alone (especially if you include Belem) is about right. There are moorish and Roman remains in Lisboa and just wandering in Alfama and Mouraria is a delight. Evora is an easy day trip by train but Obidos is not accessible by train and I’m not certain it’s worth the time it would take by bus. It is a cute town but not my favorite place in central Portugal.

The Algarve is also easy by train - at least getting there and back. Renting a car while there is advised. I can’t imagine being able to visit all the places you mention in three days. Just the beaches and rock formations around Lagos will take most of one day. Tavira is really far east and I would not spend your precious time visiting Faro. Lagos is my favorite area and can easily do a day trip to Sagres from there.
Coimbra is a great stopping point between Lisbon and Porto. And, Porto is really nice, even if you aren’t interested in the Douro or wine.
In two weeks, I would pick a total of three places to stay with a possible one night stay in Coimbra (even though it’s worth two nights). I think you will be happier if you slow down a bit. Lisbon especially is really about wandering, lovely miradouros for long lunches, etc.

Thanks! What about Sintra? It seems like there's so much to do for a day trip. Would you see it as an overnight?

There is definitely a lot to do in Sintra. Much more than one day. A lot of people recommend staying overnight but as I haven’t done that, I hesitate to give an opinion. I would suggest you research the palaces, etc. to see how many you are really interested in visiting, then make your decision.
And, try to accept you likely won’t see everything you want to see in one trip. I’ve been here over two years and still haven’t seen everything I want to see!

We've been to Portugal twice. This was our itinerary the first time, which hits many of the spots you mentioned. We chose to stay in many of the places you mentioned as day trips from Lisbon. We did it with a car. The second time we trained more, but frankly I missed the flexibility of the car. Aside from a few high speed routes we were waiting quite a bit for or on trains.

Lisbon 5 nights
Sintra 2 nights -picked up car here.
Salema ( Algarve) 2nights
Tavira ( Algarve) 1 night
Evora 3nights ( lovely drive from Tavira to Evora and we also drove to Estremoz and Vila Vicosa from Evora)
Nazare 2 nights
Obidos 1night, then drove straight to Lisbon airport

This is a bit more time than you have. You could easily drop 1 night in Sintra and 1 night in Evora, or Nazare altogether. We left Coimbra, Tomar and Porto for our second trip. I enjoyed Tomar, but would not go out of my way to see it. We went from there by train to Coimbra and it was 2 stops.

I personally think trying to do both Algarve and Porto is a lot, both are great places to see, but you will be rushing.

Have a great trip.

Hello @nipperway,

As a Portuguese I must agree with what has been said: 2 weeks for all those places is too much in my opinion.

Lisbon is the biggest Portuguese city and has a lot to see... yes, you can visit it in 2 days but you get the feeling that there is much more to see. Some quarters are amazing and just losing yourself on those streets is good enough to spend a day or two.

Sintra is one of my favourite places in Portugal (maybe the one) and I think one day won't be enough to enjoy the cultural and natural landscape and visit all the points of interest (maybe stay one night there or choose just a few places to go and return there on another occasion).

I live near Porto and you shouldn't miss it... the historic centre is beautiful but it's not only that: people are friendly and welcoming, gastronomy is great, crossing the bridge and go to Serra do Pilar viewpoint is a great experience, etc...

Coimbra is also great... it is known as the Portuguese "city of students" and it's another place to wander and admire the architecture and more: the university, Joanina library, the gardens of Quinta das Lágrimas (apart from the monasteries and cathedrals)...

I'm sure you'll make the right decision and whatever you choose I'm sure you're going to love it ;)

Thank you so much everyone! What about this?

4 nights in Lisbon (1 day trip to Obidos with a tour group)
2 nights in Sintra (maybe take train or bus to nearby place of interest like Cascais?)
3 nights in Algarve (wherever our Starwood hotel ends up, but I do like the sound of Lagos)
1 night Coimbra or Evora? Which is smaller and would be more ideal just to spend the day wandering around?
4 nights in Porto (we don't drink alcohol but a river cruise in the Duoro Valley sounds lovely, day trip recommendations?)
1 night back in Lisbon before our flight

Is this more relaxing a trip? Also, there are times that my husband tires and wants to go back to the hotel and I want to keep exploring. Does this accomodate that?

Given your stated interests, I suggest dropping the Algarve and adding those days to Lisbon. There are nice beaches in the Lisbon area, both to the west and south. These are easy to get to on public transportation in less than an hour.

The longer you stay in one place, the more you will encounter the local culture. I would recommend renting an apartment in a residential area rather than staying in a hotel.
I have visited Lisbon many times, and I am still finding new things to see and do. Note that there are more than 100 museums in Lisbon, most of which are of high quality, and many are focused on history and culture. Try an internet search - Tripadvisor has a good list.
In my opinion, Portugal is best for a slower paced trip of discovery, rather than a fast moving site-seeing dash.

Yeah we are thinking of dropping Algarve. Cascais looks pretty. Where would you recommend?