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Solo sailor Leo Goolden reports from aboard Tally Ho at roughly two-thirds of the way across the Caribbean Sea, northbound through the trade winds, on day five of a passage bound for Cuba via Jamaica.▶ 0:20 At 2 a.m. on the third night, a wooden mounting bracket for the tiller pilot split under sustained load, the autopilot fell free, and the boat rounded up into an uncontrolled crash gybe under triple-reefed mainsail and number three jib.▶ 5:30 Goolden woke to a violent knockdown, a flooded saloon, broken glass and ceramics, an inflated danbuoy in the cockpit, and the tiller jammed behind a winch.▶ 5:49 He confirmed the rig was standing, shut off a running freshwater pump, and — naked except for a life jacket — freed the mainsheet and tiller, then hove to for roughly 12 hours to rest, clean up, and fabricate a stronger replacement bracket from spare wood.▶ 6:26 He dropped the mainsail entirely and hoisted the trysail for the first time at sea, eliminating boom-gybe risk and improving control in 25–35 knots of true wind.▶ 10:51 The boat lost distance to the southwest while hove to but resumed the northward passage once repairs were complete.▶ 13:02 Goolden now plans to stop in Jamaica to refuel diesel and potentially meet crew before continuing to Cuba.▶ 16:42 The crash gybe caused no detectable rig damage; the triple reef and the switch to a trysail both limited the severity of the incident.▶ 7:43

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