Need help with itinerary ASAP please!

I don't know about what order to do things in, but you are heavy on the Lisbon area and light on the Porto area. You only have two full days in Porto.

From June 12 to the 17, are you planning to spend all those nights in Lisbon and do day trips to Sintra and Sesimbra?

Woa!
Why the sprint? Why not a stroll?
You really are on vacation for only 9 days. The day you arrive and the day you leave don't count as "vacation"
Lisbon and Porto alone will fill that. Save the Duoro for you next trip.

For a day trip to the Ocean from Lisbon, check out Cascais.

Dennis

Contrary to the others, I think that with 10 full days on the ground, you have time to visit Porto, the Douro Valley and the Lisbon area.
2 full days in Porto, as you plan, is perfect in my opinion.

Then, for the Douro Valley, you might want a car to visit the area more efficiently, and return it in Porto Campanhā station for the train to Lisbon. It would be better to spend two nights in the Douro, but I understand you want to be in Lisbon for the festival. I am not familiar with it, so i do not know if it is worth it.

Lastly, in terms of Lisbon day trips, Sesimbra is very much optional. Cascais, as suggested, is a more convenient coastal option.

Thank you everyone for the help!!
I also agree we are heavy on Lisbon and light on Porto. The reason it’s like that is because I keep reading the Lisbon festival is a must, so wanted to be back on the 12th for it.
I also don’t want to cut the Duoro Valley because we absolutely love visiting vineyards and learning about wine. And I thought it would be nice to break up all the city time.
Is Pinhao the best area to stay in Duoro?
Would it save a lot of time to rent a car in Porto to drive to Pinhao and then Pinhao to Lisbon? The car would just to get from point A to B to C. We won’t be driving in Duoro since we’ll be drinking.

Thank you!!

A word of caution about the Feast of São Antonio. The Alfama will be wall to wall people with most drinking a lot. And, there are no places to use the bathroom. That’s all I had to hear when I first moved here to make me avoid it at all costs! There are smaller celebrations elsewhere and the parades are a sight to see.

I would also leave out Sesimbra with such a short trip.

Wow that sounds miserable! Thank you for letting me know. Maybe we will spend that extra day in Porto after all.
Also good to know about Sesimbra, I was on the fence because it does seem a bit difficult to get to.

I'd spend the extra day in the Douro, not Porto. 2 full days for Porto is enough IMO, and you'll be more relaxed with one full day in the Douro Valley instead of just one night.
EDIT: I misread, you are planning 2 nights and it is fine.

And yes, on second thought driving from the Douro to Lisbon could be more "seamless". It is a four hour drive to the airport or Oriente station (my suggested car drop-off points), so you could even stop somewhere on the way. Maybe not Coimbra (worth more time), but Montemor castle or Alcobaça monastery?

My tentative itinerary was 2 nights in Duoro with half day and one full day. Do you recommend 2.5 days and 3 nights instead?

Thanks!

Oh, looks like I misread.
Nevermind, then! No need to change anything ☺️