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Second, or is it third for Portugal. There is a substantial British expat population so finding native English speakers will not be difficult.
Depending on how you define warm and sunny, you should find something that meets your definition. The climate is very similar to California. North definitely has 4 seasons. Central has 3, South has 1 season.
It is a poor country so your housing dollars will go far but it is a small country so you can live relatively far from Lisbon or Porto (2 biggest cities) and still be to one or the other in 2-4 hours.
I don’t know the big cities, my family comes from a very rural area but I would give the Algarve region a hard look. Even at 4 hours from Lisbon, you could hop a shuttle flight to Lisbon and then get back the US if need be.
I second renting and don’t be afraid to rent away from the cities. There are many safe towns where you’ll do fine with being a native speaker.
Like visiting anywhere else, an earnest effort to learn basic greetings will get you the latitude you need to switch back to English.
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