This Is What Sailing Hawaii Actually Looks Like | Hilo to Honolulu
February 11, 2026 · 24 min · 8K views · East Honolulu, United States
Sailboat slicing waves under rainbow near Hawaii
What this video covers
A Westerly Yachts Ltd. Discus 33 sailed from Hilo to Honolulu, navigating the Hawaiian Islands while managing a leaking raw water circulator pump. The crew faced restrictive local anchoring regulations, which limit stays in many areas to three days before requiring permits and fees.1:01 During the transit, the vessel encountered variable trade winds, including 25-to-30-knot gusts and swirling wind patterns near Maui.7:56 The crew navigated the narrow, shallow entrance of the abandoned Lona Harbor on Molokai, noting that large southern swells make the approach hazardous.14:21 While sailing, the engine’s raw water pump developed a steady leak, forcing the crew to minimize engine use and plan for repairs in Honolulu.5:04 Upon arrival at the Hawaii Yacht Club, the crew transitioned into maintenance mode to prepare for a subsequent passage to Alaska.21:58 The experience confirmed that while Hawaii offers scenic sailing, the combination of red tape, limited transient moorage, and challenging anchorages makes it better suited as a short-term stopover than a long-term cruising destination.
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