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I crashed my boat into the rocks. Here's the story.

November 5, 2025 · 21 min · 153K views

Damaged hull with captain's reflection in glass

What this video covers

James Evenson fell asleep twice at the helm under full sail and drove his boat onto a reef — once in 2016 on a plywood catamaran off Tulum, Mexico, and once years later on his Oyster Marine 485, Zingaro, near Nassau in the Bahamas.0:06

The first incident happened after a full day of diving near Tulum, followed by an overnight passage to find an anchorage.2:09 Around 4 a.m., exhausted, he fell asleep and grounded the catamaran on a shallow reef.2:31 Both daggerboards sheared off on impact.3:17 He kedged off using two anchors and 150 feet of chain, walking the anchor out underwater with bare feet, pulling the boat back inch by inch over three hours.4:20 A wave reset the boat to the original grounding position, forcing him to repeat the entire process.5:49 A through-hull was pushed up through the hull; he sealed it with a two-part epoxy putty stick.6:36 Repairs at Progreso, Mexico took 31 days of full-time work and cost roughly $20,000, and the boat never fully recovered.8:42

The second grounding occurred around mile 900 of an 1,100-mile single-handed passage from Grand Cayman to Nassau — sailed without an engine due to a blown head gasket.10:57 The Oyster 485's keel dropped into a coral crater and stopped the boat hard.12:34 Evenson raised sails to heel the boat and free the keel, then kedged off using 250 feet of chain, with his girlfriend Anna operating the windlass while carrying their six-month-old daughter.13:52 The anchor found no purchase on the flat reef floor until he wedged it under a ledge.13:46 Once free, the boat swung under full sail toward shore before he dropped the sails and recovered the anchor.15:27 Damage was limited to scratched lead on the keel and a chipped rudder corner; repairs two months later in Annapolis required grinding, thickened epoxy fills, and bottom paint.17:17 Exhaustion management — specifically the inability to get adequate sleep on a single-handed passage — was the root cause both times.

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Boats in this video

Oyster Marine 485Their boat

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