I Finally Sailed to Maui — Where It All Began
October 29, 2025 · 36 min · 11K views · Hilo, Big Island
Sailor steers sloop through Hilo Bay under blue sky
What this video covers
Oliver sails Phoenix from Hilo Bay, Big Island, to Lahaina, Maui — the place where, three years earlier after a neck diagnosis, he stood on a balcony and first decided to buy a sailboat and sail the world.▶ 21:01 The passage crosses the channel between Big Island and Maui, which he describes as one of the most dangerous in the world.▶ 3:22 PredictWind and Windy both forecast 5.6-foot waves; the crossing takes roughly one overnight, with about two hours of sleep, and proves uneventful.▶ 5:02 Pre-departure repairs at Hilo included fixing a disconnected bilge pump, sealing leaking porthole gaskets with Vaseline (later flagged as damaging to silicone), and inspecting the engine after two and a half days of hard motoring left soot in the engine room and a belt slowly peeling apart.▶ 1:33 The main autopilot had broken; the Hydrovane wind vane was reinstalled as redundancy, with a tiller arm autopilot as a second backup.▶ 1:23 Downwind, Oliver deploys the whisker pole for only the second time, rigs a preventer, and eventually goes wing-on-wing to stop the jib from slamming — a four-minute fix that gains 0.5 knots.▶ 12:18 At Lahaina, the marina is closed following the 2023 fires; Phoenix anchors in the mooring field off the ghost-town waterfront.▶ 20:12 Dinghy landings through a heavy shore break flip the crew out twice before they learn to time the waves.▶ 21:53
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