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Perhaps best idea is to research the areas that you are interested in (in my case it was Algarve because of weather), find out the availability and cost of accommodation, transport etc in these areas..and then book a hotel and car hire for a couple of weeks to drive around and check out areas interested.

That's what I did before settling for Albufeira which, sounds like, won't be on your own list.

Be aware, also, that each area may be far busier in high season, and very much less so in low season.

Good luck!

@LindaPR

Following, I am looking for the same information.

Hi Linda. Planning and executing such a big move on your own will not be easy. I would say that the quieter parts of the larger cities of Portugal (Lisbon and Porto) might best suit your dislike for cities and big crowds and favour for lively and joyful places. So I would focus on these two cities and explore. Both cities are very walk-able despite being on hilly terrain. In Lisbon I wouldn't look for accommodation on the flight pass into the city. Other than that a lot will depend upon your other wishes and budget.

@nz7521137

We may wish to add that if looking at both of these lovely cities, the weather may be very cold and damp at the end of the year.

If renting, the experience of uninsulated Portuguese properties may be interesting, and the delights of dining or coffees on street tables may not have the allure they have in the spring or summer months.

Hi and Welcome,

Both Lisbon and Porto are big cities which spread out at the edges and together have about 50% of Portugal population so  very easy to be overwhelmed by the vastness of both.  If you look at several of the towns in the central of the country, maybe  Coimbra, Tomar  etc they have everything needed for normal life, banks, schools, local council offices, supermarkets, pavemant cafes, estate agents, hospitals, dentist, doctors, rivers, old building, train and coach links to elsewhere (some parts of Portugal have little public transport), festivals, public art, Coimbra has an old university so has a student population and in addition  both have people who live and work there so they are not just tourist places like some of the Algarve.  If you you walk round either then maybe a week and you'd be able to find your way around the main bits without a map and even visit any estate agents en-route to see express and interest and collect info on what's for sale or rent nearby. The towns have small hotels/pensions which are in the older parts which are less accessible by car but ideal for get to know visits, so if going by car then parking on the edge of town and walking in, there is very little street crime and people tend to go to same cafe for coffee and cake breakfast for years (coffee is a way of life) and in the evenings people tend to go out for a stroll and natter whilst kids play in the old squares - well there tends to be no cars in the narrow streets.

@nz7521137
We may wish to add that if looking at both of these lovely cities, the weather may be very cold and damp at the end of the year.
If renting, the experience of uninsulated Portuguese properties may be interesting, and the delights of dining or coffees on street tables may not have the allure they have in the spring or summer months.
-@slugsurmamates

For a Canadian neither of these cities will be "very cold". When I rented arriving in Portugal (2015) I made sure that our apartment had central heating (with gas) and our apartment we bought in 2017 does have that as well. So, it exists, but is not the standard in Portugal.

Lisbon (and the surrounding area) and Porto do have a huge permanent international community, which might help the process of settling into the new environment. Overall I agree to the thought of "to each his own".

@slugsurmamates Thank you!

There's a lot to look at.  It's a small country, but full of nice towns from one end to the other.

How's your Portuguese?  I think this more than anything is going to determine where you'd do best.  I'm in a small city of 25,000 or so, depending on how you reckon it, and I don't think I'd recommend it much for someone who is not ready to start speaking with people in their language.  Though an expat couple we know is living in a more rustic situation not far away, and seems to be OK though more or less completely unable to speak Portuguese, so ... I guess it takes all kinds, but the point is, not many people here speak English.  The bank, the police, the people who deliver packages, install internet, the hardware store ... speak French?  No?  well, English a few words.  I've seen a little of that in Lisbon, to be fair, but of course not as much.

It isn't a super easy language to master.  Start now if you haven't already.

Otherwise ... go up north just to see.  Everyone warns people off the north - because they don't want their favorite places overrun by expats.  Ha ha.  Is the winter weather really the problem they make it out to be?  It's more similar than different, they still have palm trees etc.  Want to be warm in the Algarve?  No problem - it's supposed to hit 109°F Friday in Faro.  Who knows how long the water supply is going to hold out.

I spent December and  January in Porto, Coimbra and Lisbon this year. I live in Florida in the US, and although it was cloudy and rainy, the weather was not uncomfortably cold. Two of the smaller cities I visited, that I really liked were Guimareas and Avairo. Both have train stations, which is important if you will not be renting a car. I would recommend picking 2-3 cities and spending 1 month in each. Maybe one north, one central and one south. Use AirBNB or another rental service, visit the local shops, bars, restaurants and figure out what you like. Enjoy...and please let us know your experience.

@zubeala Hi, I'm Bill form Michigan. I'm thinking about spending Jan/Feb of 24.Did you eat out every day? I was thinking about hiring a cook/ housekeeper for a couple hrs. aday.

I've never been there so any hints or input would be appreciated.

@zubeala Great advice! Thank you so much!

@wmjkbutkovich I don't know, everyone's different, but we sure don't eat out every day, living here or visiting.  That to me is not so much about Portugal, but about us, how do we live etc.