Lisbon - where to stay. what to see in Portugal/Spain

You’ve got 12 full days and enough places on your itinerary for 3 weeks+. Traveling from Portugal to Spain is not easy. Distances are long. Seville is worth 3+ days,. Have not been to Gibraltar but most travelers we know though it was not worth the trip. Morocco, too distant most of your time spent traveling. Since you’ve already booked air an open jaw flight is out of the question. Use your time to explore Portugal. Much to see and do. Look at the RS tour itenarary for ideas of places to visit and sights to see.

yes, too many places I want to visit. I am narrowed down to Seville and Portugal. didn't book flight yet thank goodness.
not worth going to Morocco? good to find out ahead.

I will look at RS tours for Portugal, thank you!

TAP didn’t have a great reputation before Covid, so I have never flown with them.

The time you have is a decent time to explore the area between Lisbon and the Douro. To include the Algarve would be rushed, but to include 3 other countries is impractical if you want to visit small towns and savour places. I have found that English isn’t widely spoken in many small inland places, surprisingly.

Lisbon is a good base for Sintra and you could easily fill 5-6 nights here. The towns between Lisbon and Porto such as Obidos, Alcobaca, Batalha, Coimbra and Tomar are all worth visiting. Evora is worth 2 nights, which is also the minimum I would suggest for the Douro. It’s not going to be beach weather in October. Porto is compact and can be seen in 1-2 days.

Gibraltar IMO is best avoided unless you like tourist tacky souvenirs.

Seville can be covered from the Algarve in around 3 hours, but you need 3 full days there, ideally as there is lots to see.

The best parts of Morocco necessitate a flight, not a ferry. It’s a fascinating country and you could easily spend 10 days here.

I would just cover Portugal, as public transport links with Spain aren’t that great. You don’t want a car in Seville.

I, too, would like to visit Lisbon for many reasons. One of them is https://cooking.nytimes.com/recipes/1020555-lisbon-chocolate-cake. You said you want to experience the culture. Food is a great part of culture. Just beware the No. 28 tram!
Seville is divine especially for the Moorish tiles and architecture. We spent three days there and rented from HomeAway, now VRBO. (VRBO has its "warts", so be wary if you use them.) The prices for everything in Spain are much less than France, for instance, where we traveled following Seville and Granada. We, too, were advised not to bother with Gibralter, which was deemed too commercial. There were truly wonderful historical facts that we appreciated, but the ones we remember the most were: while visiting Madrid, Seville, Cordoba, Granada and Barcelona we learned that Columbus definitely discovered America and Queen Isabella saved Spain from the Moors by establishing Catholicism!

Morocco is a great destination, but ferries from Spain mostly go to Tangier, which is not one of Morocco's highlights. It takes time to get to the ferry port from anywhere in Spain you would otherwise be, then the time on the ferry. The pay off is...Tangier. Don't bother. The good news is that there are flights to Fes and Marrakech (two of Morocco's fabulous cities) from many places in Europe, so it's actually surprisingly easy to include some of the best places in Morocco in a Europe-focused trip. You don't have to try to cram Tangier into a trip to Spain.

We drove from Seville to Selema Portugal, a sleepy little town on the coast, spent 3 nights, travelled up into the hills for cork trees and out to Cape Sagres. We are planning on doing Lisbon and north in 2023.
We then drove down Tarifa and went to Morocco for a day trip, not worth it IMHO.
However, I will disagree with the other posters about Gibralter.
After Tarifa we were heading to the White Hill town of Rhonda and along the highway my husband spotted the Rock and said why don't we do a half day here. Best day ever. We walked through the town and went to get on the funicular when a taxi driver with a van stopped us and said "why pay 20E each to go up and just walk down", for the same money I will take you all over the island and all you have to do is pay to get into the caves. We spent 3 hours and found out more information as to the history behind the Rock. He took us to the very top where the monkeys are protected and only the drivers can feed them. Also the cave with the stalactites where rock concerts are held, and so much more.
It is well described in RS book on Spain.

I agree with many of the above replies that the itinerary would benefit from thinning out.

TAP is fine. The service is typical of the Iberian service industry—not solicitous. But a flight's a flight, and TAP often offers good value.

I like to stay on Liberdade in Lisbon. Middle of everything, walk to anything.

I agree with the others that this is way too much for two weeks. Two weeks can be enjoyed and filled with just Portugal - Lisbon, Porto and points between. Save Spain for another trip - or save Portugal for another time you won’t be able to savor anything if you rush from place to place.

TAP is fine as long as you don’t have to change your reservation. It’s become my favorite airline within Europe in the last few years. And, I just flew Lisbon to Chicago on TAP and have zero complaints. Due to covid there were 27 people on the entire flight so it was lovely. Don’t count on that being the case by fall.

And, as a tourist you might meet expats and chat with the Portuguese people. But the Portuguese are slow to befriend those of us who move here, not to mention tourists. However, they will be welcoming and want you to enjoy their country. They are much more friendly than the Spanish and (in the tourist areas) most speak English.

Thank you for all the advice! this is helping me to plan my trip for the best possible experience. Sounds like it is best
to pick just a couple of places and there is so much to explore there - rather than to try and flit about to too many locations and not
get the best or feel of specific places. now it's just a matter of picking the top 3 to start with.
one question that has come up is whether the Algarve is worth making time for instead of a different location?
My travel mate wants to kayak in the rock formations there and spend 1-2 days.

Make sure if renting a car to pick it up and return it in the same country to avoid steep drop off fees.
Andalucia should be another trip of two weeks duration.

The Algarve doesn’t have the charm of many of the places further north and with your timescale, I wouldn’t bother in October. I have had some decent days in the Algarve then, but also some of the heaviest rain I have ever experienced.

Is your friend a very strong, experienced kayaker? I have seen a couple of very fit but exhausted men in their early 20s having to be rescued from a kayak here. It was quite scary seeing a lifeguard having to drag them and the boat onto the beach.