Transportation of letter mail and individual packages falls into the most expensive category by default for any of the islands. Either regular postal service, whether air or sea freight, is logistically challenging to say the least. Also, certainly do not expect express services to provide 24/48-hour service for the islands either.
“Transportation is logistically challenging to say the least. On the other hand, once it arrives on the right island, the mail delivery may just be of a quality that belongs to the absolute outer category.”
Here, the farther from the main hub, Sao Miguel, the slower. And the more often it meets a logistics transfer point on the way from island to island, the bigger the chance of damage and/or loss. It is not for nothing that many companies even in Portugal itself do not deliver to the Azores at all, or attach separate conditions to it.
Letters will do, but especially for the holiday season, timely shipment of individual packages is advised. With a healthy margin of safety, it is preferred to be surprised for the better than the other way around.
On the other hand, once it arrives on the right island, the mail delivery may just be of a quality that belongs to the absolute outer category. Do not be surprised if the letter carrier delivers the mail intended for you where you are at that moment, regardless of the postal address provided.
Mail from the islands to mainland Portugal and beyond is generally easier than vice versa, but still unaccountable and limited in size for air freight. If you wish for a hybrid living on the Azores, then having a well-thought-out digital communication format at your disposal will be something to embrace wholeheartedly.
