The characteristics that attracted the early settlers on Santa Maria to the Baia dos Anjos—an anchorage with easy access to the shore for loading and unloading—proved attractive to others sailing the eastern Atlantic sea lanes. Pirates (or corsairs) from the North African states soon made the Azores a regular stop during their predatory wanderings. The Spanish, still not completely reconciled to Portuguese independence, felt the right to stop in on occasion to take advantage of what the locals had to offer. And in the mid-16th century, during the Spanish wars, British privateers, making no distinction between the Iberian states, raided occasionally.
Fearing sporadic attacks, the early Santa Marians decided on another site for their main settlement. On the south coast of the island, they identified a ridge, between two narrow ravines, sweeping down to the ocean, and stopping on a bluff above a bay.
The bluff was the ideal site for a small fort—Fort Brás—nothing more than a wall mounted with several cannon.
Cannons to the right of me, cannons to the left of me.
The fort offered, however, a commanding view of the bay, and any ships entering were within range of the cannon. While the fort could not defend the town itself, the narrow ravines provided a natural defense. Any pirates, soldiers, or privateers who managed to land would face a challenging, up hill struggle to reach the village, where even a small local militia might ward off any exhausted attackers who reached the top of a ravine.
The village became Vila do Porto the major (and really, the only) city on Santa Maria. The narrow ridge of the city severely constrained development to one main street running due north from Fort Brás and two parallel side streets. The tiny communities scattered over the island are not very far from this local metropolis, but the twisting, narrow roads that wander across the island make for slow, arduous journeys.
The move to Vila do Porto proved successful, somewhat, and militia fought off several attacks throughout the 16th century. Pirates are, however, resourceful, and on several occasions, ships landed attackers further along the coast out of sight. They managed to escape detection, climb the ravines, and assault the local population. To be sure, the island offered little plunder, but slavery was still a flourishing trade, and many Santa Marians were carried back to North Africa and sold.
Today, only seagulls guard the bay.