How To Sail To Hawaii

If you do not regularly sail the seven seas yet want to know how to sail to Hawaii, you must be either crazy or rich. The channels between the islands are notoriously treacherous and are named accordingly. The Pailolo channel between Maui and Molokai means ‘crazy fisherman’ and the Alalakeiki channel between Kaho’olawe and Maui means ‘weeping baby’. To get to the Big Island of Hawaii, you will have to brave the Alenuihaha channel which means ‘great billows smashing’. That is the crazy part.

To sail to Hawaii, you will need:

  • A sailboat
  1. Know what you are getting yourself into. Most people will start this journey in Oahu. As you sail south, you will have an amazing time island hopping and wonder what all the fuss is about. The fishing is incredible out there. You will see dolphins, maybe even whales and the views of the islands as you drift by are truly one of a kind. But when you start to swing around Maui towards Hawaii, things can get ugly quick. The distance between Maui and Hawaii is only 30 miles. Unfortunately you must sail between two dormant volcanoes. Haleakala on Maui is more than 10,000 feet tall and the awe inspiring peak of Mauna Kea rises almost 14,000 feet like a god above Hawaii. The winds that scream across the Pacific get funneled in-between these giants and intensify. You can sip your Mai Tai in Kailua-Kona with the balmy trades blowing fifteen mph while the wind in the channel is howling over 50 mph. This wind creates monster surf. Twenty foot surf is insane. Never mind those extreme surfing videos. They go down once. Try going up and down for several hours nonstop while begging the Polynesian sea gods for mercy. The Alenuihaha is so unpredictable that NOAA has designated its own page for forecasting this elemental beast.
  2. The easy way. If you are rich, you can charter a 50 foot sailboat for around 2500 a night. They will gut the marlin you catch, grill it up for you with a miso glaze and serve you drinks as the sun sets into a tropical sea. But if you want to sail to another island, you must add at least another grand, and even more if that island is Hawaii because of the tempestuous Alenuihaha channel.
  3. The hard way. At Honokohau harbor in Kailua-Kona, you will see men who are professional sailors wobble into the Harbor House bar and lay on the ground. They claw at the floor to steady themselves after the treacherous crossing between Maui and the Big Island. Riding up and down waves that are taller than street lights will do that to a man. But if you are determined, your first step is to read the NOAA weather reports. Don’t even try it if there are small craft advisories in the channel. Wait for perfect weather, it’s your best chance. You should also buy a water proof VHF radio with GPS and memorize where the distress button is. More often than not, the tricky winds in the channel will not allow you to actually sail. Make sure your engine is in perfect shape. Think about how much fuel you need and then double it. Tell the harbormaster in your last Maui port what you are up to and how many people you have onboard.


  • Alenuihaha is pronounced ‘Ah-le-new-ee-ha-ha’.
  • Learn the correct pronunciation of the Hawaiian sea deities to intersperse in your prayers for mercy.
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