Sailing Through History

Posted on 1/27/2026 04:00:00 AM in Traveler Spotlight

By Steve Cutright, 20-time traveler from Pinole, CA

Our trip with O.A.T. on The Wilderness Beyond: Patagonia, Tierra del Fuego & the Chilean Fjords was aboard the Stella Australis, an expedition ship well-outfitted for such a trip. Here was a chance for Rena and I to explore an area of the world as exotic as it is storied: the Tierra del Fuego Archipelago and its southernmost point, Cape Horn of South America. We already had an appreciation for the Southern Ocean, having crossed the Drake Passage to Antarctica two weeks before.

Some of my ancestors developed an appreciation for these waters, as well. The last time anyone in my family had been to the Cape Horn region was in September of 1869. The Gregory's, a family of five, had arrived in New York from Liverpool, shortly to book passage around "the Horn" on the Young America, a three-masted extreme clipper ship out of New York Harbor bound for San Francisco, a voyage of 13,328 nautical miles (over 15,300 statute miles). Like many immigrants to California, they were headed to the gold fields in the Sierra Nevada. My direct connection with the family was with the eldest daughter, Mary Emma Gregory, at the time a 15-year old English girl who, two years prior, had been formally introduced to Queen Victoria. Mary Emma is my great grandmother.

Approaching the Horn had its own special drama for us. As we traveled south, the wind became stronger and the seas larger. We arrived off the east side of Isla Hornos later that day to find conditions too rough to land on the island. The scene from the ship's top deck inspired awe. While watching the combers hit the landing beach, the monster waves off the rocky point, and the roiling ocean south of the Cape, we were suddenly hit by a local wind event called a Willowa. Over half the people on the fifth deck were knocked down by a hundred-plus mph wind blast.

The reputation of this area began to take on personal meaning for me. In the four hundred years since its discovery by serious mariners, Cape Horn has been much storied, much feared, and much respected as the roughest ocean stretch in the entire world. Never so much as in the Golden Age of Sail. To take a square-rigged ship around the Horn was considered the ultimate test of seamanship, unsurpassed by challenges elsewhere. And the world's shipping in those years paid a steep price at Cape Horn. The monument on Isla Hornos is to the mariners who didn't survive the passage: over 800 ships of that era were lost attempting to round the Horn, and over 10,000 sailors perished. That's not including their passengers. Today, rounding the Horn is considered to be the Mt. Everest of ocean sailing.

The Young America had a precious cargo. And my trip to Cape Horn was a voyage of personal discovery. In my mind's eye as I gazed into the southern seas, I saw through the mist the outline of tall ship beating to westward in the teeth of a gale, its sails reefed, waves washing aboard her starboard beam and over her bow, her helmsman at the wheel, and her master on the poop deck beside him, braced against the wind and sea with a wide stance. As the image faded, a wave of thankfulness washed over me—for my trip and for theirs.

Experience Cape Horn and Tierra del Fuego with O.A.T. during The Wilderness Beyond: Patagonia, Tierra del Fuego & the Chilean Fjords.

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