Hello,
I have lived in alentejo and algarve, and spent a bit of time in andalucia and the canaries, also working remote, now settled in winter in algarve.
All those locations are a little bit tricky in the summer, it gets very hot and crowded, their sweet spot is mid season, winter can be (too) big.
Alentejo has relatively weak waves especially in sines area and milfontes rivermouth, great for foiling, surfing is good too. Not much protection when too big.
Algarve is more powerful on the west coast, on smaller days still super fun to foil. The south coast is more foil friendly as the swell wraps around. A growing community of foilers there, maybe 5 proning and 10+ winging. Lots of expats living there, integration is easy, that is to me the special thing there.
Andalucia has great weak waves, el palmar works great for surfing and foiling, lots of winging. But less swell than portugal because of the swell shadow.
Canaries also really good, especially for winging, surfing is tricky, lots of localism.
If you need more info or visit the algarve feel free to shoot me a dm I’ll be happy to help.
Remy