Drake’s Bay—Part 2, The Voyage of the San Augustin

In 1565, Phillip II of Spain claimed the Philippine Islands (hence the name) to take advantage of the profitable trade in the region which included the Spice Islands (Moluccas), China and the Philippines. Because the Portuguese commanded the trade routes around Africa, the Spanish galleons had to take another route.

They sailed from Spain to Mexico then traveled overland to what is now called Acapulco, built galleons on the beach (later most were built in the Philippines) and sailed to Manila (no doubt they went to get a shipload of those terrific envelopes). There they cruised about loading up on spices and silk before heading north as far as Japan to catch the winds blowing east all the way to the coast at today’s Oregon/California border. From there they turned south to Acapulco. They loaded the goods on wooden-wheeled oxcarts, driving them 450 miles to Vera Cruz where they were transshipped to Spain. This took two years and it was insanely profitable, enough so that the Manila Galleons as they came to be known, made this run from 1565 to 1815—250 years!  

Returning from Asia is where scurvy became a problem. This lack of vitamin C caused old wounds to open, bones to break, gums to turn black and teeth to fall to the deck like spring rain. This wasn’t a problem on the outward bound leg as there were plenty of dried chili peppers for everyone, but on the way back these were relegated to the officers. The cause and prevention of scurvy was unknown. If they had just eaten seaweed they could have kept most of their teeth

You might think that it would be smooth sailing once they got to the coast of California where they could reprovision, but after wrecking a galleon in Oregon they dared not get too close to the coast. You see, the ships could not ‘point‘. That means they couldn’t get too close to the shore and sail against the prevailing winds which were nearly always aimed at the rocks.

What they needed was a safe harbor that they could sail into and turn into the wind. There are only two such places where this could reliably happen. One is San Francisco Bay, which went undiscovered until Portola saw it from the hills near San Bruno in 1769. And the other is Monterey Bay, which was discovered by Juan Cabrillo in 1573 but then some bonehead lost the map and its location remained a mystery for another 150 years.

The Spanish did attempt to find a harbor. In 1595 Sebastian Cermeño, captain of the San Augustin, left Manila in July and first sighted land in early November. In addition to trading in the East, he had been charged with finding what was up with the shoreline and reconnoiter for a place to resupply. Sebastian sailed down the coast from Oregon without any luck until he rounded a point of land and anchored in a large tranquil bay. Hooray, a safe place to anchor! The next day when most of the crew was ashore, heavy rollers caused the ship to drag anchor and it was soon beaten to firewood on the beach—and wet firewood at that. The Miwok Indians milling about were delighted by the mysterious object that came crashing ashore with its magical bounty spilling forth from the hold.

Several of the crew drowned but seventy men found themselves shipwrecked on the sand and completely destitute. Still business was business, so Sebastian claimed the land for Spain and named it the Bay of San Francisco, a name later applied to the larger bay to the south. He told the locals, in Spanish no doubt, that taxes were to be paid and they would have to stop having sex in the open, dancing and running about naked. All the gunpowder and most of the swords had been lost, so the Indians just laughed and kept on dancing. A few years earlier the Indians had been made subjects of the English Crown so they didn’t mind it a bit as their new status came with iron nails, fantastic brass buttons and bits of Ming China—all of which they greatly treasured.

Sebastian salvaged a small launch from the wreckage of the galleon and, using the now abundant planks littering the beach, raised the gunwales to accommodate 42 of his men. The crewmembers set sail on a 2000-mile journey to Acapulco, trading shards of china and tatters of silk fabric for food from the locals as they made their way along the shore. Trash from the world beyond was like moon rocks to the Indians.

The first stop was the Farallon Islands, about 25 miles southwest of Pt. Reyes. This course took them far enough out to sea that they missed discovering the entrance to San Francisco Bay. Continuing south, Sebastian mapped Monterey Bay and San Diego before finally arriving at his homeport in Mexico.

The remainder of the crew in Drake’s Bay said they’d had enough sailing plus the boat would have been impossibly overloaded, so they generously offered to go by land and said, ‘no, you take the boat, we’ll grab a cab.’ As no cabs were available, they walked. Amazingly, everybody returned back safely—even if the hikers were pretty tuckered out and immediately imprisoned for mutiny on the technicality that they had abandoned ship. Ouch!

The failure of this enterprise caused Spain to steer well clear of the coast; a fact that allowed the locals to keep running around naked for another couple of centuries. The ship’s loss also led to a policy of land-oriented rather than sea borne exploration and, as a result, the San Francisco Bay would not be discovered by the Spanish until Portola showed up in 1769.

The San Augustin wasn’t the only ship wrecked on this treacherous shore. There are at least 72 other marine disasters in Northern California recorded during the period 1840 to 1940 alone, resulting in at least 30 wrecks in Drakes Bay or on the Point Reyes Headlands. I have rounded Point Reyes many a time in seacraft worthy and less so. It isn’t the Straights of Magellan exactly, but the swells rolling down from Alaska become pinched as they crowd around the point and bunch up with the ferocity of a skinny dog on a pork chop.


An Easter egg is just a reward for reading this far. It doesn’t occur often and has nothing to do with the above topic. This is a video which plays in the Standard Hotel in NYC. It’s my favorite video. https://vimeo.com/5082155


  • Rebekah Witter says:

    Another fun trip with you around the Bays!
    The video seems to be a bot of Hieronymus Bosch and Salvador Dali meets Cirque de Soleil – with sound track from King Kong….

    Happy Trails to you and yours always!

  • Dick Henning says:

    Can’t wait for this COVID 19 is over so I can visit the Standard Hotel in NYC!

  • ollie says:

    That Video was

    A lot of cool history I never new
    I only ask is it always history or herstory (hysterical)

  • ollie says:

    That video was

    that was some history i never new

    by the way is it always HIStory or can it be HERstory either way hysterical

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