Going With the Wind

Sailing the islands is a carefree and leisurely way to experience Hawaii’s natural offerings

By: Christopher Pala

Sailboat Excursions
Opting for a sailboat excursion gives
clients a new perspective.
From the Seychelles to Belize, Tonga to Tahiti, fleets of sailing and power yachts, crewed and not, await the adventurous traveler in search of the beauty and isolation of hidden coastlines.

But not in Hawaii. The hundreds of yachts that crowd the clubs and marinas of Honolulu are owned by Sunday sailors who rarely venture outside of Oahu’s southern coast, in the lee of the tradewinds. Since wind tunnels between the islands can make for rough sailing, Hawaii has a reputation as too hard to cruise. As a result, the 7 million annual tourists who visit Hawaii rarely get to see some of its most spectacular scenery: the coastlines that are inaccessible by road.

However, there are two outfits that cater to the market of elite travelers who want to develop a leisurely intimacy with the Hawaii that the Waikiki crowds only see in postcards. One is high-end and the other is more affordable.

Sailing Options
Pacific Yacht Management operates two sailboats, charging $4,200 per day, captain and cook included, for passage on a 57-foot Beneteau. Clients pay $2,400 per day for an excursion on a 42-foot Catalina, and each vessel comes with two staterooms. Pacific Yacht runs perhaps six charters a year, and it advises its clients fly, not sail, across the channels between the islands. Pacific also offers popular shorter trips on a 65-foot catamaran for $1,000 per hour, with a two-hour minimum.

I gravitated to a cheaper alternative. Mike Mickelwait has owned and run Honolulu Sailing Company for 30 years. His secret to keeping costs down? Instead of selling pleasure cruises, he runs a one-man sailing school that offers week-long sail-and-learn cruises for $1,425 per person, per week. When he’s not out with students, he charters his boats a Beneteau First 427 and a Hunter 54 to experienced skippers for $5,000 per week.

Mickelwait is 66, trim and laid-back as can be, tanned the color of copper. He’s pathologically attached to his baseball cap wholly inappropriate headwear in strong winds, but an excellent source of man-overboard recovery exercises for his students. He claims that he has never had a major problem in all his years of sailing.

“Anyone who can sail the Windward Islands in the Caribbean or deal with the Meltem [the powerful Mediterranean wind] can sail the Hawaiian Islands,” he said.

On the trip, I joined a couple from Idaho who owned a little 28-foot sailboat back home, but who wanted to learn to do things the proper way; and a city planner from Honolulu who simply wanted to learn how to sail on a Beneteau.

Honolulu Sailing Trip
Laima Langley of Lake Pend Oreille,
Idaho, gives sailing a shot on a
Honolulu Sailing trip in front of Molokai.
On a sunny Saturday morning, we left behind the skyscrapers of Honolulu and Waikiki and the fleet of Sunday sailors just as the breeze was firming up. The crossing to Molokai in 18-knot winds was pleasant, and our sloop felt perfectly at ease under reduced sail.

The western end of Molokai was beige, low and scrubby, though it turns green in winter when the rains come. A little before sunset we pulled into cozy Sand Bay, on the leeward southern shore. After a dinner of Peking duck that I had bought ahead of time from Honolulu’s Chinatown, we went to sleep to the gentle rocking of the swell.

The next day we crossed over to Lanai, which is about half the size of Molokai. As we cruised past the western coast, a seemingly endless, idyllic and absolutely empty beach unfolded. We lunched and snorkeled, marveling at the wealth of marine life compared to Oahu. As we sailed onward, the beach rose to a series of desolate, spectacular cliffs, culminating at 1,000 feet. Not long before we reached Lanai’s Manele Harbor, with its little marina, we passed a series of striking rock pinnacles and noted several good anchorages. After dinner, we took a walk to the Four Seasons Resort Lanai at Manele Bay, whose spectacular atrium is studded with the personal collection of Asian art and antiquities of billionaire David Murdock.

The next day we stopped at a sort of tropical Giverny. Years earlier, on a deserted beach, a Maui company had built a day camp for tourists in a coconut grove, complete with a pond and a gazebo. It had been abandoned and the ground was littered with coconuts, one of which we opened and savored in the sort of delicate, mottled light that Monet would have loved.

The crossing to Maui was 15 miles and no bumpier than the others. We cruised past the beautifully preserved town of Lahaina, the former capital of Hawaii, and anchored in the heart of the condo/hotel strip of Kaanapali Resort, taking in shopping and an excellent martini at the Sheraton Maui.

Mickelwait had saved the best for last: a cruise along Molokai’s north shore for up-close views of the world’s highest sea cliffs, which rise to 3,300 feet. Thickly coated with native vegetation, they undulated like curtains and sprouted high white waterfalls everywhere. We stopped in front of Halawa Valley and gaped. There’s nothing quite like it anywhere in the world. And to think that most clients only see it by helicopter, where the time to watch is measured in minutes, not hours.


Honolulu Sailing Company
Commission: 10 percent

Pacific Yacht Management
Commission: 10 percent