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It sounds like you have been doing some fairly good research so far, but we don't know ... for example, everything was pretty close to the sea, until we got to Coimbra, and it might help to know why that pops up.  In terms of the physical situation - there are few places on earth as nice as San Diego, and frankly I haven't seen this in Portugal, but I haven't been to the Algarve.

The ideal thing, as you know, is to be able to drift around a bit to get some real sense of what places are like, maybe year around, but then it isn't that small of a country and the difference from one side of town to the other might be larger than between one town and another.  But as long as you're in the vicinity, I'd have a look at Leiria, and maybe one of the smaller towns like Porto do Mos.  There are nice towns along the coast to the north that are fairly popular expat destinations, like Aveiro and Ovar.  And the Setúbal district to the south could be a little warmer weather than all that.

As I never tire of pointing out, the language here is Portuguese, and it's a good idea to start in on that while looking at travel brochures.  Or if you don't really expect to climb that mountain, that's a factor - probably forget Leiria etc., you're going to need to stick to peak tourist areas.  In practically any place big enough to support a major grocery, the walking distance goal will be easy to satisfy, but the meeting your neighbors goal is maybe a little more hit and miss, and of course if the neighbors need to speak English, that's an issue.  Our neighbors are all somewhat past middle age, and one of them knows a few words of English.  Their adult children can mostly manage a little, but .. I can't say for sure that anyone is really eager to go there, you know - the ones who chose to live outside the Portuguese speaking world, are not here.

@donn25 Thanks for taking the time to reply.

I am studying Portuguese for an hour most days (at least five days per week), so I should know enough for a friendly conversation by June (I learn quickly) and be quite comfortable in another 14 - 16 months. We both expect to speak more Portuguese than English after we arrive, and we'll start speaking it at home now for the things we've learned to say.

We live slightly inland now, not on the beach, but we can get there readily. We thought we'd check Coimbra because of the University (we've always lived in college towns) and because it's warmer without being as tourist-filled as the Algarve. The temperature concerns me less than reports on the wind, although maybe I read reports from people who want to keep expats away... I'd like to live somewhere I'd want to use my balcony or patio on a sunny day. We have an onshore flow here - there's always some breeze - but it's rare to have it so strong that we're tying things down or not wanting to go to the beach or be outside. I'm trying to determine if the coast (Figueira da Foz, Nazaré, etc.) will have that same issue. Hubby would really like an ocean view, but that's a want, not a need.

San Diego is lovely, but the cost of living is sky-high and rising fast. They say the cost of living in Portugal is 40% that of the United States, but that is for *most* of the United States. It's about 20% that of San Diego. San Diego is also crowded. We've seen it triple in size in the 42 years we've lived here. We're ready for a community that feels like a community, a slower pace, and the chance to immerse ourselves in the local culture.

I've heard some complaints about wind, but not specifically the places you mentioned so far.  Lourinhã, could be?  It's bound to happen of course, but I've been to Figueira da Foz a couple of times and didn't really notice it.  If there were a down side to the weather there, it would be that it can be cool and grey when it's hot and sunny here (we're close enough to Coimbra.)  Not a major difference, not as bad as I experienced in Ventura's "June-uary", but you know what I mean.  It freezes a little here, and doesn't often in the places you mention, so that's something, but for me ... I'm here for the sun.

Coimbra is a good example of how easy it is to have a bad example.  I've been there a few times, as it's the closest big city on the train, and I don't look forward to it at all.  Not anything specific, just doesn't appeal to me.  But we were there with a friend who lived there, and kind of experiencing it like she does, ... OK, maybe I can see it.  Or there are a thousand places you could end up around the city, that each would be significantly different.  Anyway, the main complaint I've actually seen about it, is that the students are noisy.  Figueira da Foz though I liked.  Nazaré is more touristy / beach town. 

@gwalks

why not considering the whole region?

@Santi2

I don't know what to think about this.  The same thing from you, over and over -- link to a site about Tomar.  It would be nice to have you some time genuinely participate in a conversation, not just pitching your real estate.