Lisbon, Obidos, Porto

Way too ambitious unless you enjoy spending all your time in transit & checking in/out of hotels without experiencing anything. Don't forget jet lag.
Douro Valley is a 2 hr train or 1+1/2 hr drive to Peso da Regua from Porto. Penhao is another hour further. If it's the wine & port you are interested in, you can enjoy them in Porto & across the harbour where the warehouses are.

You are trying to squeeze a 10 day itinerary into 4 days. Far better to spend all the time in Lisbon, which needs 2 days itself. Sintra and Cascais are the usual day trips from there (a day each). You can take the train to these destinations, but for your itinerary, you would need a car.

Thank you.

So I've scratched a couple places off my list and narrowed it down to these two options:

Stay in Lisbon at the same Airbnb all 5 nights. Do not rent a car. Do day trips via train or bus to Sintra, Obidos, and Porto. Fly to Barcelona from Lisbon.

-OR-
Stay in Lisbon one (or two) nights, then have a road trip. Hop in our rental car and stay one night in Obidos and one (or two) nights in Porto. Fly to Barcelona from Porto.

Does Option 2 still seem too ambitious, hectic?
Thank you!!

I would definitely stay in Lisbon the entire time. There is so much to do in Lisbon and surrounding areas, changing accommodations/locations would just waste precious time. Spending three days in Lisbon/Belem then a day trip to Sintra would fill your time and you would get a feel for Lisbon instead of just rushing from place to place.

Day 1 will work,
Day 2, you plan to go to beaches and then Douro Valley. Not sure where in the valley you plan to go. your Day 3 is in Porto, which is in the valley. We recently spend 14 days in Portugal and part of that was a Douro River cruise for a week. We loved the cruise and the Valley. Not sure if you are driving a rental car or taking the train. There is a train that goes up the valley from Porto. However, you won't be able to see much with two days, one of which includes Porto.

Porto is wonderful, we liked it better than Lisbon, however, if you want to see the Douro Valley right, do a river cruise or spend 4-5 days there. I think your proposal 2 works better. Plan on visiting the valley on another trip.

You can't miss Sintra, if you like palaces and beautiful views it's one of the prettiest. What are you interests? Castles? Beaches? Culture - port/shows/museums?
You can do Lisbon in 2 days. If you like music, sneak in a fado dinner show
Do a day trip to Sintra and one to Queluz
Obidos is a must see too. That would be your 5 days

Porto is beautiful, but best saved for another trip when you can do the river cruise and see the north.
I see you're heading to Barcelona after, one of my favourite cities in Spain. Enjoy!

Thanks so much everyone, for your input! Much appreciated.

After much deliberation I went ahead and booked two nights in Lisbon and two nights in Porto.

I also booked a rental car for days three and four (as soon as we leave Lisbon). I'd like to drive in the most scenic way to Obidos before heading (again in the most scenic way) to Porto. Please send recommendations and thoughts on places of interest along the way, for the drive up north.

And what else around Porto would be wonderful to see in terms of making use of the rental car?

The thing that I am still vacillating on is canceling the rental caer taking a bus to Obidos and a train to Porto. I would only want to make use of a car if there were some super amazing places along the way that we would not otherwise be able to see.

Thanks again for your thoughts!

And we are planning to visit Sintra as well, on day two in Lisbon.

As far as a scenic drive, please don't expect there to be seaside roads. I drove all over the Silver Coast last year and didn't really find any. There are brief stretches but I think they would take you so long, it wouldn't be worth it. The biggest thing you could do with a car in Porto is visit the Douro valley. But you could also do a day tour from Porto. However, with only two nights in Porto, you could definitely stay very busy in Porto itself.

Hi Camilla,

I think you made a great choice. Obidos is adorable, but if you get there early in the day (from Lisbon) you could experience it in a day, and still make it to Porto. We stopped in Batalha, Altobaca, and Nazare, each relatively near Obidos.

Happy to provide more info if you wish,
Robert in Montreal

Regarding Porto, I would allot at least two days to see the city. The Douro River valley wonderful. Best way to see it is on a river cruise. Our river cruise was seven days and we visited Salamanca, Spain as well. If you don't want to do that, you could drive, but I suspect the terrain would make driving slow and not sure you would see the valley that well. We noticed that there is a train that goes alongside the river, you might check that out. Also, there are shorter cruises up the valley.

You only have four days, so I suggest planning on visiting Porto and the Douro Valley on a separate trip, unless you extend your vacation time.

Obidos has a great hotel in the old castle there in one of those Government run historical hotels. You can see Obidos in two hours.