9 days in Portugal - 25th anniversary trip

Most people day trip to Sintra since it is so close and very easy to get to. You can take the train or Uber/Bolt. Since your trip is short in duration, one less hotel move would probably be for the best, so I wouldn't overnight there.

Are you flying to Lisbon from the U.S.? You will waste your arrival day due to jet lag. Do Sintra as a day trip the next day!
It sounds like you want to avoid visiting most of Portugal’s top sights? Only 1.( days for Lisbon? Skipping Porto??And instead go to a beach in the Algarve?

Thanks for the replies!

The Algarve looks gorgeous with the cool rock formations there — I’m surprised you wouldn’t rank it as a must see. Also as it is an anniversary trip we want to enjoy relaxing more than we normally would on a typical trip.

I had heard from a friend that Lisbon was nice but I didn’t need all that long there. We are not huge museum people (and in our 40s/50s so not doing night time city stuff).

And yes we are flying in from the US - direct flight from the east coast.

I think you need to spend some time looking into Lisbon especially since you mentioned not being museums or night life individuals, which makes me think perhaps you have not done much homework on the city. Lisbon isn't a place that one typically spends time in museums, at least not in the traditional sense. Lisbon is one big outdoor art museum with its tile work (azulejos) and street art. Wonderful views and Manueline architecture. It's a city that one just wanders around and soaks up the views and beauty. I never walked into a museum and not into night life, but after a week there, I still felt like I did not have enough time.

Thanks, Lynn. That makes sense and was actually more what I thought we'd be doing there. I mentioned the museums and nightlife only because 1.5 days of walking around exploring a city's vibe would usually feel enough for me and DH. Working within the confines of our short US vacations and the $$ of flights to Europe so doing much more of a highlights visit than a thorough exploration of the country and its cities.

I'd really appreciate any other input from folks on whether the hike up to Douro is worth it given the time we have vs. exploring pretty winery areas anywhere else?

Uber does not exist in the Azores. Bolt is only available in Ponta Delgada, Sao Miguel.

Renting a car is the optimal method for sightseeing in the Azores, except on the island of Corvo, which does not have any car rentals. Nor would a car would be necessary on this tiny island.

You mentioned Azores, but did you mean Algarve?
The Alentejo region is the big non-port region in Portugal. We don’t drink wine anymore, so skipped that area, but if you look up ‘Alentejo wine hotel,’ you’ll get lots of options. Once you get your hotel, you may want to ask them if it’s more feasible to Uber or have a rental. I’m going to guess the latter, because the villages are pretty small and spaced out.
We stayed in the eastern part of the Algarve, on the Rio Formosa, which was perfect for us, but not right on the Atlantic. Even Rick Steves beloved Salem’s is quite built up.

Oops! Yes Algarve. :)

You have received some good suggestions here. Since it is your first visit to Portugal, and you do not have much time, I would recommend spending a few days each in Lisbon and Porto. Some of the reasons already mentioned regarding Lisbon also apply to Porto. Douro is also very worthwhile and given your time constrains I would recommend seeing it as a day trip from Porto. There are many options for guided visits which would probably be best in this situation. Douro is the most beautiful wine region that I have seen (and I am from San Francisco and owned a home and vineyard in Sonoma). And long gone are the days when Douro was strictly Port country. Some of Portugals finest red and white wines come from this region. I agree with the advice to skip the Algarve on this visit.

I will echo the others who recommend skipping the Algarve. Yes, the rock formations are lovely, but spending your time between Lisbon and Porto is much better for really getting the feel of Portugal. The Algarve is really only about the beaches.