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A custom aluminum sailboat, *Gypsy 2*, encountered severe weather during a 1,400-nautical-mile passage from Virginia to the British Virgin Islands.0:05 Shortly after rounding Cape Hatteras, the vessel entered the Gulf Stream and became trapped for 96 hours in a tropical depression followed by a low-pressure system.25:39 The crew faced 35-to-40-knot winds and steep, 15-foot seas with periods of less than six seconds, forcing them to sail erratic courses to avoid the worst of the conditions.26:28 The autopilot failed during a 25-knot gust, requiring manual intervention to prevent the boat from rounding up.17:03 Throughout the passage, the crew managed sail configurations using a Walder boom brake and a double-reefed main, though they struggled with inconsistent wind and short, choppy waves.11:57 The experience resulted in extreme seasickness for one crew member and forced the vessel to deviate significantly from its intended route.36:38 The boat’s structural integrity remained intact throughout the storm, confirming its capability in heavy weather.34:16

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