7 nts, into and out of Lisbon-advice re: Lisbon or Porto first?

Wish I could be more effusive about Lisbon.

I'd spend 2 nights there, then half a day. That should provide close to 2 days of sightseeing there for whatever specific sights interest you.

I'd leave for Porto in the afternoon of Day 3; 4 nights there would mean you wake up in Porto on Day 7... and with an additional half day for Porto that morning; in the pm of Day 7, catch a train back to Lisbon for a final night's stay near the airport.

Days 4-6: work in a day trip or half-day trip for a visit to Guimaraes, or for a wine tour or train trip up the Douro Valley.

Definitely do a day trip to Guimares, Portugal’s first Capital.

Hi! That sounds like a great trip, you’ll love Portugal in September.

As for the structure of your itinerary, both options are doable, but here are a few thoughts that might help:

• 1 night Lisbon → 3 nights Porto → 3 nights Lisbon: This gives you more time to settle in Lisbon at the end, which is nice since your flight departs from there. It also avoids a rushed final travel day. The downside is only having one night in Lisbon at the start, which can feel short after an international flight.
• 3 nights Lisbon → 3 nights Porto → 1 night Lisbon: This gives you a better buffer after your flight. You can take it easy, enjoy the city a bit, then head to Porto when you're more rested. That said, the single night in Lisbon at the end could feel a bit tight depending on your flight time.

I’d lean toward the first option, it’s a bit more relaxed at the end and works well with your flights. But if you’d rather ease into the trip with more time in Lisbon up front, the second one still works well.

Either way, Portugal is very easy to get around by train, and both cities are fantastic!

As for day trips:

• From Porto, I’d recommend Aveiro and Costa Nova. It’s a lovely mix of canals and colorful beach houses, and it’s actually between Porto and Lisbon, so easy to reach.
• From Lisbon, a day trip to Sintra and Cascais is a classic.

Since you're not renting a car, booking through GetYourGuide is a good call. You'll find many tours and it makes things easier.

Let me know if you need more information or assistance with your itinerary!

Thank you all very much!

We think that flying into Lisbon and immediately getting on the train to Porto might be too much for us. Have you done this?

To answer this question, we took the train the same day to Porto after a flight from the West Coast. The flight landed in the morning, we took the metro from the airport to Rossio, stored our luggage in one of their lockers, walked around to work off our stiff legs, getting lunch, then took the train to Porto from Santa Apolónia train station. Took a nap on the train, and then arrived in Porto to check into our hotel and got dinner. It worked well for us. I had bought the train tickets in advance to get the discounts, thus why a bit of a gap between landing and catching the train. But those few hours also let us take a break from sitting. I like to have my days grouped together and reduce location changes.

I also recommend Guimarães and Braga for potential day trips. I'm not sure which one I liked better.

If you're still deciding on the best itinerary between Lisbon and Porto, I’d just like to reinforce that starting with 1 night in Lisbon, followed by 3 nights in Porto, and finishing with 3 final nights in Lisbon is a very balanced option. It allows you to ease into vacation mode, enjoy Porto at a good pace, and return to Lisbon with enough time to explore the city without rushing.

While in Porto, I highly recommend doing a walking tour to get a solid introduction to the city’s history and culture. I recently joined the Food and Wine Tour by Bluedragon Porto City Tour and it was honestly one of the highlights of my trip. The local guides were knowledgeable, the food stops were delicious, and the stories really brought the city to life — it’s a great way to discover Porto through the eyes of locals.

As others have mentioned, the train between Lisbon and Porto is very comfortable and runs frequently. Booking in advance on the CP (Comboios de Portugal) website can also help you get better fares.

Wishing you a fantastic trip — Portugal is an amazing country!

Thank you so much for the responses. We will stay one night in Lisbon and then go on to Porto, back to Lisbon at the end.
Two follow up questions, probably many more to come...

One to Debora (or others) do you recommend food tour in Porto over in Lisbon (that's what I had been thinking.)

Does it sound good to try for Baixa hotel on night one, and when return try for Chiado area? I realize that we are a little late on the booking.

Thanks again!

Does it sound good to try for Baixa hotel on night one, and when return try for Chiado area? I realize that we are a little late on the booking.

Both are good neighborhoods (centrally located), Baixa being flat and Chiado on a bit of a hill, but very close to each other. Some accommodations will actually put Baixa-Chiado as their location.

Below is a link to their metro stops. So, if you stay in the Baixa-Chiado neighborhood, it will be very close to Santa Apolonia train station, which is the one you will be taking to go to Porto (metro blue line)
https://www.metrolisboa.pt/en/travel/diagrams-and-maps/

The Rossio train station, which is right by Baixa-Chiado, will take you to Sintra, which is a great day trip. The train station is very close to the Rossio metro stop. But you can walk from where you plan to stay.

I would recommend heading directly to Porto by train upon arrival.  Over the years, I have found that I actually prefer to get more travel out of the way on arrival day.  I am so tired from jet lag, I feel like a better investment of my time is to close my eyes on a train for 3 hours (and get it done now rather than later on in the trip) rather than try to keep my eyes open at 8am in a new city.  Then you minimize switching accommodations, and time back and forth from the airport and train stations.  I also preferred Lisbon to Porto, so I would rather finish with Lisbon.  A highlight of our trip was the organized bus day trip we took from Porto to the Douro Valley.  If this were my trip, I would go immediately to Porto, 3 nights in Porto (one of which would be a day trip to Duoro Valley), 4 nights in Lisbon (including a day trip to Sintra).  With more time, I would have loved to squeeze in a stop or a night in Coimbra in between.  We stayed in Chiado and loved it.  I can recommend a simple place for fado in the neighborhood if you end up staying there.