Webb Chiles

 Solo Two-Stop Circumnavigation
San Diego
Start & Finish
October 18, 1975 - October 1, 1976

About 24,000 nautical miles, 202 Sailing Days, 118.80 Miles per Day
No engine on board, 28.5' ft  LWL, 37.4' ft LOA
(Average 4.95 knots), 0.927


© Richard Konkolski


His original name was Webb Tedford. He was born on November 11, 1941 at Saint Louis, Missouri. When he was 8 years old, his father committed suicide in 1949 and year later he was adopted by stepfather and his name was changed to Chiles.

In 1963 he graduated college and moved to California where while working various jobs he was writing. In January 1967 he bought his first 26’ boat – Excalibur sloop and two years later the second one, 35’ Ericson 35 sloop, which he named Egregious. In September of 1973 he purchased a new bigger engineless boat Ericson 37' cutter, which he also named Egregious.

He lived on his boats and taught himself how to sail and navigate during preceding six years to his first solo circumnavigation. He made a couple of five hundred mile long passages along Californian and Mexican coast and feel experienced enough to take on the Cape Horn after divorcing his second wife Lynn. Actually, at present time (2007) he is married to his sixth wife Carol.

  Webb Chiles at Newport, RI - 1992

In November 2, 1974 he sailed from San Diego, California for his first attempted solo circumnavigation via Cape Horn. The sea and solitude were new to him, but technically he feels to be a good sailor accepting that nobody knows the sea until one makes long passages offshore and that nobody knows solitude until spending months if not years alone.

As he left the San Diego Bay, his rudder almost immediately start grinding and moaning and the water start filling the bilge through some leak below the waterline but those problems did cause him to change his course for the Cape Horn. On November 20 he was awakened during night by a hard, clear metallic crack. He rushed on deck but could not see anything out of place; he discounted the sound and went back to bed.

The weather was getting worse and when the noise appeared again Webb did not have to move from his berth to find the trouble. A few feet away from him the two half-inch stainless steel bolts securing the mast to flanges near the overhead were broken. He remained hove to until dawn, when he sawed some wooden wedges and drove them around the mast. This took several hours before he was able to turn south again.

This was his first full mid-ocean gale during which he also discovered leak in hull. He was already at 11° S and 122°W with Cape Horn four thousand miles to the southeast and Tahiti almost two thousand miles west, but the closest place downwind where he could make repairs to the rudder and the rig. He had no other choice then on November 21, 1974 to turn to the wrong way – to Tahiti for repair. The gale continued for two more days during which he lost his autopilot’s servo rudder. Only the leak was smaller on downwind track.

He reached Tahiti on December 5 and as soon as he received parts, he was ready for Cape Horn again, leaving Papeete on December 23, 1974. Ten days later on January 3, 1975 he entered the Roaring Forties for the first time and the next morning he awoke to a strong wind, which soon broke the tangs and bolts replaced in Tahiti. After limping all the way back to San Diego, five thousand miles north, under severely reduced sail, setting only the storm jib as a headsail he got back at the start point where Egregious was extensively repaired.


On October 18, 1975 he left San Diego again and sailed for Cape Horn and even hull cracked in gale near the Equator November 1, 1975 could not stop him. It was December, when after fifty days and six thousand miles of sailing south, his course was finally east for fearful cape. On his third attempt he was getting very near, but for luck of Sun he was not sure about his position.  His dead reckoning put him on the latitude of the Diego Ramirez Islands, some fifty miles southwest of the cape. Later the cutter passed south of the southernmost of the Diego Ramirez Islands. The wind was only twenty-five knots, but the surf against the green-gray cliffs was impressive.

Then the wind increased quickly to a gale. By dawn it was blowing fifty knots, and during the day it built to a full Force 12. The mainsail ripped. All his sails were not strong enough for his voyage and without spare sails they required continuous repair work. All his hardship was soon rewarded by a great feeling of becoming the first American to round Cape Horn alone on December 12, 1975.

Two days after the Force 12 wind off Cape Horn, Egregious sat becalmed on a flat and glassy sea. The crack in the hull seemed manageable and wanting to get as far as he could during the southern summer he kept sailing. By mid-January he was about halfway between Africa and Australia, at latitude varying a few degrees either side of 45° south. Week later, on January 21 he capsized in Southern Ocean. Next day on January 22 he capsized second time shredding his storm jib. His face was hit with a drawer full of books, his stove went out of order and Webb was left with cold food.

Without a storm jib he had no choice but to lay ahull, the sun was briefly visible late this morning and he got a sight which put him at 43°44’S, but he had to guess the longitude. By dead reckoning he was near 63° E, the antipode longitude of San Diego. Africa was two thousand miles behind and Australia two thousand miles ahead. 

January 24 Egregious was again knocked down, and Webb was washed overboard, hanging in space and water until he swung back aboard. His safety harness was clipped on, but he was happy not to be forced to test them. The January 25th storm was over with broken bolt connecting the tiller to the rudder post only. 

South of Australia, on February 13, the barometer began a steep decline like he never seen before.  The day was to be far beyond his experience. He was struck by strongest wind ever experienced south of Australia, guessing around one hundred knots. Fortunately that incomparable wind passed within an hour, leaving him to lay ahull to a fifty-knot gale. The next morning he was able to set the storm jib, only to discover that the self-steering gear was dismembered.

On February 20 he passed Southwest Cape, Tasmania and on February 28, he crossed 40°S and left the Roaring Forties. He thought he was passing into safer waters, but on March 5, on his 140th consecutive day at sea he had to lay ahull in the Tasman Sea bailing water from the bilge. Three huge waves struck him in rapid succession. The first two knocked him down; the third rolled Egregious over to port and forcing him to sail for Auckland, which he reached after five months at sea on March 16.

The rest of the voyage was relatively easy. After repairs he sailed from Auckland on May 7 and on May 26, 1976 he arrived at Tahiti. Three months later on August 29 he sailed from Tahiti for San Diego, where he arrived on October 1, 1976.

His two-stop solo circumnavigation voyage was 348 days long with 202 sailing days, Webb Chiles did not pass antipodes.

© Richard Konkolski

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