John Gilpin set sail from New York City on October 29, 1852, arriving in San Francisco in 93 days, 20 hours, under the command of Captain Justine Doane.

Clark describes the race between the two leaders, Flying Fish and John Gilpin, as follows: The fleet was so large in 1853 that it was not uncommon for two or three ships to be in company at sea, each striving to outsail the others.

The John Gilpin sailed out past Sandy Hook, October 29, 1852, followed by the Flying Fish on November 1st, and before the green Highlands of Neversink had disappeared below the horizon both ships were under a cloud of canvas.

She dashed down southwardly from Sandy Hook, looking occasionally at the charts; but feeling proud in her sweep of wing, and trusting confidently in the judgment of her master, she kept, on the average, 200 miles to leeward of the right track.

Rejoicing in her many noble and fine qualities, she crowded on her canvas to its utmost stretch, trusting quite as much to her heels as to the charts, and performed the extraordinary feat of crossing, the sixteenth day out from New York, the parallel of 5 degrees north.

Now her heels became paralyzed, her fortune seems to have deserted her awhile —at least her master, as the winds failed him, feared so; they gave him his motive power—they were fickle, and he was helplessly baffled by them.

Chances and luck seemed to conspire against him, and the mere possibility of finding his ship backstrapped filled the mind of Nickels with evil forebodings, and shook his faith in his guide.

The Sailing Directions had cautioned the navigator again and again not to attempt to fan along to the eastward in the equatorial doldrums; for by so doing he would himself engage in a fruitless strife with baffling airs, sometimes reinforced in their weakness by westerly currents.

The Sailing Directions advise the navigator to cross the calm belt in as straight a line as the winds will allow, not fearing the land about Cape St. Roque, or the current that is supposed to sweep round it.

Nickels, forgetting that the charts are founded on the experience of great numbers, being tempted, turned a deaf ear to the caution, and flung away three whole days and more of most precious time dallying in the doldrums.

Leaving the spell-bound calms behind him where he had undergone such great trials, he wrote in his log as follows: " I now regret that, after making so fine a run to 5 degrees north, I did not dash on and work my way to windward to the northward of St. Roque, as I have experienced little or no westerly set since passing the equator, whilst three or four days have been lost in working to the eastward between the parallels of 5 and 3 degrees north against a strong westerly set"—and, he might have added, with little or no wind.

The Wild Pigeon arrived first off Cape Horn; but here she met with a westerly gale which detained her ten days, while her competitors, the Fish and the Gilpin, were coming up fast with fine winds and flowing sheets.

[4] On November 30, 1857, John Gilpin left Honolulu, Hawaii, with 15 passengers aboard, bound for New Bedford, Massachusetts, carrying a cargo of 7500 barrels of whale oil.

During the voyage, on January 29, 1858, about 150 nautical miles (280 kilometres) off the Falkland Islands, John Gilpin struck the underwater portion of an iceberg and began taking on water.