Destroy my Paradigms! Where should I live?

Since my first visit to Portugal (1996), I've been drawn here. Due to my career (mainframe computers), PT was never a wise fiscal decision.

Retirement happened. I can leave US.
I have some paradigms. I love the Lisbon area. I love the Porto area.
Algarve sounds interesting. I visit it early September.

Where makes sense? Money is not a big issue as my pretax retirement is $5000 (4500Eu?) per month, with another 3000 or so that I must withdraw from retirement investments or face a large tax penalty.
I like the urban (actually suburban) areas of Lisbon and Porto - great mass transit, easy shopping, short trip to salt water for fishing, .... Algarve (Faro, Lagos, Portimao) seems like a lower key possibility, but one which makes owning a car more important.

Is there somewhere better?
An active English-speaking community would be a big plus. Walk/bus/train to needed shopping would be a plus. Difficult access to salt water would be a HUGE minus.

For housing, I've usually lived in a detached (no shared walls) property. It seems that whenever I've shared a wall, the neighbor has been a loud rock band or motorcycle gang. I will need 2BR (me and infrequent guests), a decent kitchen, and climate control. OK if the climate control must be an add-on like space heaters and room A/C, but prefer central.

For those who have made the move, where do you live. What do you like / dislike about it? If you would prefer to live elsewhere, where?

Please help! I've been gone from PT for only a week since last trip, and am having withdrawal symptoms!!