Lisbon / Cascais / Porto trip planning

Getting from Cascais and Porto isn't that easy. Can you fly into Porto and depart from Lisbon? That would save backtracking, although your open jaw ticket might be more expensive. If it's significant and you still want to try to squeeze Porto in, the trains from Porto to Lisbon are fast and not expensive. With an 8 day itinerary, if you're planning to spend a couple days in Lisbon and a couple in Cascais, you really don't have time for Porto, too.

Thank you. I was thinking of spending 4 nights/5 days combined in Cascais / Lisbon and then 4 nights / 5 days in Porto. I can try to fly into Porto then out of Lisbon so I only have grounds transport one way. Would that be a workable plan?

For most, the balance would be 6 days in Lisbon/Cascais and 2 in Porto. Getting between the regions will take you half a day door to door, so it’s more efficient if you don’t back track.

Alternatively, Lisbon, Cascais and Evora will fill your time without needing an open jaw ticket.

I recommend staying in Lisbon and visiting Cascais as a daytrip. We spent 5 nights in Lisbon. It's a wonderful city with lots to do. Excellent museums, interesting neighborhoods for wandering, the castle, Alfama neighborhood (the oldest in the city), and the Belem district with the Jeronimos Monastery, Belem Tower, Monument to the Discoveries, and Coach Museum. I recommend a daytrip to Sintra to visit its many castles.

Thank you! What district in Lisbon is recommended for first time visitors?

The best transport between Lisbon and Porto is by train. It’s easy and economical. You can taxi, Uber or metro to Oriente station from the airport to catch the train. You might want to look at Rome2rio for details. A driver would be very expensive comparatively.
Regarding Lisbon vs. Cascais. The only reason you might consider Cascais over Lisbon would be if your teens want beach time. While I love Cascais, there is no comparison between here and Lisbon for things to do.

Thank you all so much!

My wife and I have twice stayed in the Principe Real (near Jardim Fialho de Almeida; a lovely little park) and plan to stay there again when we return in June.
It is a quiet neighborhood with its own fish market and restaurants and not overwhelmed with tourists. You will have easy access to all the places in Lisbon you will want to see.
Dennis

Thanks Dennis!!!

I would consider flying into Lisbon and return from Porto. That way you don't waste anytime backtracking. We did that a couple of years ago (from Toronto) and it worked out great. Saved time and money versus a return trip by rail and it was actually less expensive at that time to book the open jaw ticket. As far as how to split your days I would agree with other replies to spend a bit more time in Lisbon. There's lots to do there (especially for the teens). One suggestion for something fun is to take the ferry from Cais Do Sodre across to Cacilhas. The views of Lisbon from there are really awesome and there's a lot of great restaurants where you can eat outside. If you're interested in naval histroy the last ever sailing ship commisoned in the Portuguese navy is a minutes walk from the ferry station on the Cacilhas side. Another somewhat off beat site is the Prazeres Cemetery in Lisbon. It's very different from what you'll see in North America. The ride there in the traditional Lisbon Tram is kind of cool too. One last recommendation while in Lisbon, visit Ajuda Palace. I'm not sure why it doesn't get more love in all the guides to Lisbon but it is really amazing and certainly when we were there not at all crowded. Porto is also an amazing place to visit. Of course the Ribeira and Port Wine tours are must do's. The teens may love Livrario Lello, the bookstore upon which Hogwarts library is modelled. Also, you can rent bikes and ride out to the Foz Do Douro (the ocean). If bikes aren't your speed you can take a tram right to the oceanfront. You will have a great time. Both Lisbon & Porto are two of my favorite places to visit with plenty to see and do, friendly people, and pretty reasonable prices. Hope you have fun!