From Oahu to Kauai by catamaran


As with many adventure stories, this one started in a bar. Sipping a post-work CoCoNut Porter at the Yard House in Waikiki with Jim — a family friend who’s well connected in the sailing world — I imposed the request that led to the story.

“You’ve got to get me on a sail to Maui,” I said to Jim.

“You want to go to Kauai this weekend?” he replied.

Lucky for me, Capt. Jon Jepson was sailing Makani, a 65-foot catamaran, to Port Allen, Kauai, for a private charter bound for the Na Pali Coast. Jim, a sailmaker, had a set of sails he needed to deliver to the Garden Isle. I would help in exchange for an experience I was compelled to satisfy — a sailing trip across one of Hawaii’s legendary channels. I lucked out on a good one. After all, the Kauai Channel was the only passage King Kamehameha was unable to complete.

Cruise on a Catamaran


Makani, Kewalo Basin, Honolulu; (808) 591-9000, Morning, afternoon and evening sails, from $35. Private charters also available.

Holo Holo Charters, Port Allen Marina Center, Eleele, Kauai; (808) 335-0815, Operates a sailing catamaran and power catamaran for excursions to the Na Pali Coast and Niihau. Trips from $99.

Fast-forward three days and I was standing barefoot on the deck of Makani. It was 4 in the morning, and a chilly northeast breeze was blowing. After a quick introductory handshake with the busy crew, dock lines unfurled and Capt. Jon motored us out of the Kewalo Basin Harbor with “Hell’s Bells” blasting loudly enough to turn heads at a still-open bar on the marina’s edge.

It took us only a few thousand feet before Honolulu’s incandescent glow faded and the dark sky opened into a dot matrix of starlight. The green and red flashes of channel marker buoys and the running lights on tankers were now the light of our world. Capt. Jon manned the wheel, which left me and the crew — Johnny, Barrett, Woody, Anna and Bria — with time to rest and contemplate the radiating universe.

Capt. Jon steered Makani around Barbers Point, an industrial region that gave way to Ko Olina, a resort area on the west side of the island. As we began our ascent up the leeward coast, the Waianae mountains rose overhead, casting shadows that stained the ocean black.

We were only three hours and 20 miles from the harbor, and with about 95 miles still ahead of us, I began to get excited about what we would see. I wondered what I would feel like when I hit that open ocean with no land in sight.

“Has anyone ever been to Kauai?” I asked the crew.

“You haven’t been yet?” Capt. Jon asked.


“Oh, you just wait.” That didn’t help ease my suspense.

An hour later and we were nearing the beautiful and isolated Yokohama Bay. Kaena Point lay just ahead. Just as the native Hawaiians believed that Kaena Point was the soul’s departing place from the physical world, we were now migrating from the comfort of solid landmass. Beyond Kaena Point was the seemingly endless ocean. There was no escaping it. Even if you were to close your eyes for the next six hours, the constant rocking would be a persistent reminder.


As soon as we hit the Kauai Channel, the trade winds hit us. The Waianae Mountains no longer rerouted the wind.

“All right, guys,” Capt. Jon said.

Johnny, Barrett and Woody knew what to do. They were off and running to the lines. The sails were going up, and the motor was shutting down.

With the sails up and the trades blowing, we cruised at an average of 10 knots, about 11 1/2 mph. Wind waves slapped the sides of the catamaran. Salt, deposited on the ship from evaporated seawater, caked my palms as I used the handrails to wobble around the craft. I held the railing as I stared north. Kauai was somewhere out there in the monstrous Pacific.

Nothing but white caps, flying fish and Bob Marley would accompany us for the next 85 miles.

“Some people just lose it,” Jim’s voice said as it replayed in my memory. “They just can’t handle it.”

There’s a metaphysical theory that states that our universe exists in four dimensions. In other words, our universe is one infinite gelatinous pancake stacked on top of many, many other infinite plasmic pancakes. With that said, being surrounded by thousands of miles of water was not at all worrisome. There was an entire universe below our sailing vessel. We are never really alone or isolated per se.


As we drifted across the open ocean, I began to realize that this was the destination. As soon as we docked at Port Allen, I would be surrounded by the pressures of modern society — cars, cellphones, traffic lights, a boss who wants to me to work on my day off and a Labrador retriever that eats five cups a day of $60-per-bag dog food. This was an escape from it all.

“You doing all right?” Johnny asked me as I stared at the ocean.

“Absolutely. I’m just relaxing.”

Johnny smiled. His white teeth contrasted against ultra-tan skin. All eight of us were burned cocoa from the seven direct hours under the Hawaiian sun.

I watched a set of gray storm clouds at the horizon’s edge.

The closer we bounced and rolled toward Kauai, the bigger the dark smudge grew. I rocked to sleep on the nets at the bow of the catamaran. Lilac water “shushed, shushed, shushed” underneath as I dozed off. When I came to, Kauai was in front of us.

White water exploded against crimson cliffs. Basalt climbed out of the deep ocean and led to the dramatic, near-vertical volcanic peaks that brought the movie “Jurassic Park” to life.

As we sailed around the southern perimeter of Kauai, we passed the resorts — none taller than a coconut tree — of Poipu, beautiful coffee plantations that had recently sprung up on hillsides overlooking the ocean, and the greatest treat of it all, Niihau, the Forbidden Isle, an unimposing rocky blurb on the horizon.

As we stepped off the Makani and onto stable ground at Port Allen, I felt as though we all had l accomplished something. In reality, it was a pleasure cruise, an 11-hour tour. I realized I would never attempt it in a war canoe, even if it were alongside Kamehameha.