First trip to Portugal - itinerary check?

The Douro Valley is more about the scenic vineyards lining both banks of the river and the wineries (with guest houses). And I wonder how scenic the vines will be that early. I was in Tuscany and Umbria in late March and the vines were all just black stumps. For a small town experience, choose one of the towns near Porto, or Coimbra on the train line between Lisbon and Porto.

I was in Lisbon March of 2024 and thought it was the perfect time to go. I will be retuning next March.

My trip report might give you some ideas for Lisbon:

https://community.ricksteves.com/travel-forum/trip-reports/solo-in-lisbon-portugal-my-trip-report

I also flew from Chicago, and you can read about my flight and airport experience. Keep in mind, my trip was pre-EES.

The smaller cities on the Douro (upriver) are Regua and Pinhao.

You don't need a rental car, you can take the high speed train from Lisbon to Porto, then take the train up the river to Regua and/or Pinhao. The train tracks run along the north side of the river.

A car would provide you with flexibility.

A great B&B in Porto is The InPatio Guesthouse. It is fabulous, but book early.

We were just there a few weeks ago. In the Douro, Regua was much bigger than I expected. Not in a bad way, but did not feel like a small town. Pinhao is much smaller, but while I thought it was a beautiful setting, it might feel too small to fill a full day. We had a car, though, and were able to drive around to different wineries and towns (really enjoyed Lamego and Amarante). We stayed in a quinta that was ~20 minutes outside of Regua (very narrow roads to get there, but not very much traffic, so only a few harrowing moments!) Highly recommend looking for the "miradouros" on Google maps - those are viewpoint pullouts. Agree that the vines may not be very green in March, but the terraced hills and the river will still be pretty.

We stayed at InPatio Guesthouse in Porto. I second the recommendation. Rooms were spare, but nicely updated (and the shower was WONDERFUL). The owners, Olga and Fernando, were so kind. The breakfasts were great - they try to include a different local cheese and meat every day. Also, fresh OJ! I really liked Porto. The city itself was fun to explore. We were there 6 nights (we were there for a work thing for part of the time). Some highlights: food tour (Taste of Porto), went out to the coast (while the trolleys were fine, I thought the views were better on the bus because it was a double decker), toured the Pinhais sardine factory (highly recommend), did a day trip to Coimbra.

Thanks, all, for the feedback! I'm now wondering if finding a city/town between Lisbon and Porto more along the coast might be a better bet based on the time of the year we will be there. Also thinking train instead of a car could be a better bet.

Appreciate the help! :)

How about Nazare?