Recommendations requested for itinerary : 7 days in Portugal

We were there in late September/early October in 2024 and the weather was a mixed bag of shorts and raincoats, often at the same time. Even in the rain it was so humid that I was glad I was wearing shorts, and it was never cold. I was colder in the evenings in San Francisco in August on a visit a few years ago than I ever felt in Portugal.

Even though we enjoyed Porto more than Lisbon I'd still take a day from Porto and tack it onto Lisbon. One regret we had is not dedicating more time to Sintra. We did a daytrip and felt it was rushed.

My wife and I made our first (and only) trip to Portugal in Aug 2023. We spent 10 nights, with 8 of those nights in Porto (4 nights) and Lisbon (4 nights). Our trip report might be a useful point of reference: https://community.ricksteves.com/travel-forum/trip-reports/trip-report-portugal-aug-sep-porto-coimbra-lisbon-then-to-spain

I was in Lisbon a few years back the third week of October.

It was very rainy. There were sometimes downpours. Be certain to bring rainwear just in case.

I remember it being warm sometimes uncomfortably so. Have no memory of cold but I am looking through pictures and I see people wearing sweaters and jackets. However some have them tied around their waist.

And it was still crowded but manageable.

Lisbon was incredible.

From Porto, I took a shore excursion to Braga. Also incredible.

You are going to have. a wonderful time.

Seems like like flying into Porto and out of Lisbon, or vice versa, would save a train ride. Temperatures should be fine in early October.

@Allan, @GeoffB, @bostonphil7, @jaimeelsabio :

Thank you all for your feedback.
I gather Oct will be rainy and humid, but not cold.

@Allan - I agree, San Francisco gets uncomfortably cold most of the year.
@GeoffB - Your trip report is very helpful.
@bostonphil7 - Thank you for your tips
@jaimeelsabio - your suggestion >>flying into Porto and out of Lisbon, or vice versa<<
is a good one, however, we are not gaining much as far as time (flight lands at 1145 in Lisbon, next
feasible suggested by Tap Air Portugal is at 2pm landing at 3pm in Porto .. and adds up in cost.
And then from their to city center will be another 45 minutes or so.
Taking the train (we will be jet lagged anyway) at 2pm will get us into Porto city center around 5pm.

Otherwise, do you see any red-flags in our itinerary ?

Thu, Oct 1 : Flight from SFO-LIS
Fri, Oct-2 : Land in Lisbon. Take train to Porto - hope to clear jet lag
Sat, Oct-3 : Porto
Sun, Oct-4 : Porto
Mon, Oct-5 : Porto
Tues, Oct-6 : morning train to Lisbon, check in to hotel. Half day sightseeing Lisbon
Wed, Oct-7 : day trip Sintra
Thu, Oct-8 : Lisbon
Fri, Oct-9 : Lisbon
Sat, Oct-10 : Flight back LIS-SFO
<<

Just realized, 12-Oct (Monday), is Columbus day holiday - we might be able to add two extra days.

Air Fare is also lower by $465 for the three of us, if we come back Monday.

I think your itinerary looks great for a first visit to Portugal. October is usually a very pleasant time to visit, with mild temperatures and fewer crowds.

Since you'll have three full days in Porto, consider spending one day exploring the historic center, Ribeira, São Bento Station, Clérigos Tower, and the famous port wine cellars. If the weather is nice, you could also take a tram or walk to Foz do Douro and enjoy the beaches along the Atlantic coast. A beach day is a good option also and try our famous seafood restaurants.
I wouldn't try to add more destinations. Porto, Lisbon, and Sintra will give you a wonderful mix of history, culture, scenery, and local food without feeling rushed.

Enjoy your trip, you'll probably leave wanting to come back and see more of Portugal!