Recommendations for a first trip/scoping retirement options

We are in Sintra right now and just had a long chat with a couple traveling through Europe by car. Just for your info, they said driving on Portugal’s roads has been very challenging.

Scope the residency visa possibilities first.

Evora was a wonderful place to visit - dinner at the Pousada was a treat, too. On 2 trips to Portugal, I’ve stayed in Obidos both times.

Happy hunting/researching!

Heads up, the Algarve coastline is the Atlantic.
We just finished our 3 month winter trip in Portugal - mostly the Algarve - and can attest that the ocean water is very cold.
The further north the colder it is.
At times the ocean is just as rough as it is in Nova Scotia.

Air temperatures were ok for most of the time, like Florida in the winter.

If you had the option to work from home full time, you could investigate Spain's digital nomad visa and move now.
I am assuming you have read all the expat websites and watched the numerous You Tube videos of countries to consider? I won't be moving, but do use them for research for winters away (from Ottawa). Though I haven't investigated many options yet. There has certainly been a rise in lodging costs since the pandemic and the I crease of global digital nomads. A penpal is an expat and for her, things have gone up 35% while her friends say even more. I have been searching month or more rentals and prices since pre covid are up 60-80%. Understandably the Med coast is popular...so now you will be competing with several generations not just fellow retirees.....and be sure to watch the public reaction to increased shortage of local and affordable lodgings.

I've done a few rounds of scoping out for long-term. While it can be combined with sightseeing, there should also be plenty of time given to wandering residential neighborhoods, going to supermarkets, and stopping to look in real estate office windows (or idealist.pt for the town you're in), unplanned stops to have a coffee/lunch/drink when you see locals (whether native or expat) gathered in a plaza or terrace, etc. A spreadsheet or Pro/Con list is maybe overboard, but it's not a bad idea to make a few notes about what you've liked and disliked about places, so you can have greater clarity understanding your needs and wants.

But Mr E is right—get your head about residency requirements and tax consequences of a move. I understand Portugal is one of the easiest and cheapest for Americans in those regards—It could be different for different nationalities.

Vis a vis what MariaF wrote, I read that Portugal is eliminating its so called Golden Visa where you could get Permanent Residency by bringing in a certain amount of investment money

You may want to look up the D7 Visa.

I applied for the Golden Visa before it was abolished.

The D7 is more affordable, but requires physical residency before you get citizenship.

Portugal is a great place to retire in. Things are affordable and English is well understood.

JoAnne, if you are pretty serious about relocating to Portugal and checking out cities and towns to retire in, look at the FaceBook group, Americans & Friends-PT. It has a plethora of info on visa requirements and generally, moving to Portugal.

In addition to residency and tax requirements, learn about inheritance taxes, too. In France, we have a certain number of Americans who decide to go back or become part-time after they learn about
the difference in what will go to taxes rather than their offspring compared to the US. Finally, be sure you don't fall in love with a house in a medical desert.

I’m American and have lived in Portugal for seven years - so have a good amount of knowledge about making the move. What the others posters wrote about Americans and Friends in Portugal Facebook group is correct. You can find more than you could ever want or need in their files. My friend, Susan, started the group 5 years ago and it’s an amazing resource. Portugal has become very trendy with Americans and other North Americans - so much so that a number of people make the move without being fully prepared for the differences in lifestyle, housing, bureaucracy, etc. Therefore, a number of them leave after a short while. I absolutely love it here and would be devastated if I were forced to leave!
The places you list are good for a visit, but don’t forget Lisbon and, even Porto. Porto will be colder and wetter but many people settle there. Be aware that the Algarve will be flooded with tourists in the summer and many places are closed up in the winter. Evora and the entire Alentejo, gets horribly hot in the summer and colder in the winter but is a great place to visit. I love Cascais but the prices have skyrocketed since I’ve been here. We have a huge immigrant community here with many ways to meet people. Caldas is very popular but Ericeira has a good number of expats also. Coimbra is becoming more popular with expats.

Most of the towns popular with expats/immigrants have Facebook pages that include monthly activities such as happy hours, coffees, etc. That might enable you to meet others who have moved while you are here visiting. I agree totally with the suggestion to visit supermarkets and local farmers markets while you are here. The Mercado in Cascais is a vital part of my weekly life and would give you insight as to some of the differences in shopping opportunities.
Have fun with your planning. I’m happy to help if you want to send private messages, also.