To me it seemed that the north coast of Pico facing Sao Jorge would probably offer best coast launch spearing. For BW I would head for south of Pico or to that strait between Pico and Faial.
Well...after all the distances are very short, so if one has a good boat, you can go anywhere!!! Faial, Pico, S.Jorge....all very close to each other.
Oh..so you got lured to the cellars??
That explains why you call the Faial facing part "eastern"???
Oh...S.Miguel (Ponta Delgada) was terrible...will never set my foot on that piece of rock again.
Cheers,
Mikko