Living the dream circumnavigating ‘low key’

Globe-traveling Capt. Woody Henderson sailed to see

Capt. Woody Henderson sailing out of San Francisco delivering a racing yacht. Photo courtesy Woody Henderson

Idyllwild resident Woody Henderson has roots on land, but he has lived his adult life at sea.
His father bought the Idyllwild cabin in 1974 that Woody now calls home. But it was the South Bay, Manhattan and Hermosa Beach where he grew up and like many beach kids, he was drawn to the water.
In his early 20s, while living in the South Bay and operating his own company installing mini blinds, Woody had an epiphany. “It was when my roommate packed up his stuff and moved to Hawaii,” he said. The roommate explained he could work construction from anywhere and Hawaii had a special island pull.
“I had avoided having a family so that I could travel,” Woody recounted. “I did the math and realized I could see all these places more cheaply if I sailed there, working my way. I met a couple who had this 65-foot yacht and they needed a crew to go to Europe and back. That’s how it started.”
Woody was 25 at the time. For the next 25 years, his life was an adventure, lived at sea, visiting many of those out-of-the-way islands and cultures he had always dreamt about experiencing.
Chance often played a role in the unfolding of his life, as did his inherent optimism.
While in Gibraltar, he struck up a conversation with a worker associated with one of the yachts in port. “He had the crew uniform on,” Woody recalled. As fate and luck would have it, the worker was the one making the decisions — a member of Malaysian royalty spending his last free months at sea before taking on official duties. “This was his one big chance to be one of the people,” said Woody. And since Woody’s dream was to sail across the Pacific, fortune smiled again when his new friend said, “We only need the fourth [crew member] for the Pacific.”
From February until November 1996, Woody served as officer of the watch from St. Thomas, Virgin Islands to Thailand, from the Caribbean through the Panama Canal and across the Pacific to Asia, followed by some races and regattas in the Malaysian Sea.
With a clean wake trailing, Woody took two years to circumnavigate the planet from May 2003 to May 2005, including a treacherous trek sailing south from Madagascar and rounding the historically hostile Cape of Good Hope from the Indian to Atlantic oceans.
For 13 of his sailing and exploratory years, Woody wrote a well-read “life-style” column for Latitudes and Attitudes Magazine. He also opened, taught, tested and ran Coast Guard licensing schools in California for MarinersSchool.com.

The cover of Capt. Woody Henderson’s book, a collection of his articles from Latitudes and Attitudes Magazine — a lifestyle account of his years at sea, in port — what was exciting, what was challenging, what was funny, lessons learned and how he “messed up.” Photo courtesy Woody Henderson

For the last 20 years, he has been captain and owner of Adventure Voyaging, fielding a global flotilla of sail charters, captains and crews of catamarans and monohulls, with two to four cruises per year.
“I also do captain work for Sea Shepherd, the save the whales group,” said Woody. “I specialize in moving their new fleet of ex-Coast Guard patrol ships long range. They are 110-foot patrol ships that do 30 knots with 16 onboard. I’ve run those boats in their ongoing Vaquita campaign in Sea of Cortez. It’s a few weeks a year.”
He told of single-sailing the Indian Ocean as part of his two-year circumnavigation of the world, shrugging off two staggering episodes of massive waves crashing down upon his boat. “While I was watching what was happening, I put myself in the mindset of the boat,” he remembered. “It did not seem to know or care. It’s always a good idea not to let your emotions take over.
“I lived my dream of seeing stuff. Early on, when I was crewing, I would notice an island that we had just sailed by and I would think, ‘I would have stopped there.’ I pursued that dream, seeing those out-of-the-way islands, realizing that I did not get in to sail but to see different cultures and places. I held on to the dream and worked.”
Along the way, Woody taught many who sailed with him. “I like people to know and be safe out there.” His collection of Latitudes and Attitude stories was published in book form, “Circumnavigating Low Key — Where a small boat and a smaller budget lead to a big adventure.”
Curiosity and working methodically are lodestars guiding how he lives his life. “I see the window or opening, and I always go in,” he said.
While in Tonga and Tahiti, Woody began filming with drones, to better promote his projects. Returning to the Hill, he is expanding that service as a tech advisor to the Pine Cove Water District board.
Woody’s drone shots of the repairs of Highway 74 are being seen by Hill residents anxious to understand the degree of destruction and the repair processes. He is planning to expand his client pool to include local realtors.
“I’m doing the drone work as part of trying to scale back some of the more dangerous boat deliveries,” he said.
When Woody wrote for Latitudes and Attitudes, he captured what life felt like at sea, and on land in small harbors, on remote islands, and in native villages, and how a simple life can have its extraordinary pleasures. “I think our society could learn a lot from cruising and village life,” he wrote.
“Is there hope for those people commuting their lives away? I like to think so. I see a time when our streets are green belts traversed by foot traffic, bicycles and quiet shuttles. People work mostly from home spending the time they save not commuting on higher quality experiences like being outside and saying hi to the neighbors, spending quality time with the next generation, and walking to their local shops where goods were brought in from sources closer to home. For the rest of us, it [that vision of life] would be a nice place to visit between cruises.”