Alright – so today we’ve got the honor of introducing you to Woody Henderson. We think you’ll enjoy our conversation, we’ve shared it below.

Woody, appreciate you joining us today. Are you able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen?

Dad would say, “Do what you love, eventually someone will pay you for it.” Well I wanted to travel to beautiful places and experience new cultures. In high school I installed window coverings. After high school I was running my own window covering business while attending business college classes. I was a big fan of the independence of working for my self. That is until a few years later when my roommate up and moved to Hawaii. I realized that though I had avoided having a family I was still tied down by my business. I broke up my business and sold off the parts.

I worked as a bartender while developing my plan to travel. I discovered that there was this group of sailors called “cruisers”. They traveled the world at a fraction of the cost of flying and hotels while being able to visit islands that were only accessible by those in boats.

That’s what I wanted to do. I could use some experience though. I found a yacht that needed a crewperson, sold everything else I had and sailed off with them. We sailed through the Panama Canal, across the Caribean up to the Mediterranean. We had great adventures. I got a paid crew position on the Raja Muda of Selangor’s yacht and crossed the Pacific. I did some yacht racing and a couple of yacht deliveries. With the sea miles I was able to get my Coast Guard license and get paid for running boats in the US. I would later circumnavigate in my own little boat.

My passion was for difficult boat deliveries, from country to country. Later I became friends with sailing legend Tania Aebi and we continue to this day to run fun flotilla trips around island groups around the globe. We enjoy sharing our experience with others.

I will always encourage, especially young people, to follow their dreams. Find their work in an industry that they love, that they were built for. For they are one and the same.

Woody, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I mentioned my early years in offshore sailing. One of my favorite things is still yacht deliveries. My crew and I move boats for owners from country to country. I have achieved being one of the primary captains for the Swan Program from Offshore Passage Opportunities. Swans are big beautiful sailing yachts. This group of Swans must move from New England to el Carib in the fall and back to New England in the Spring so their owners can enjoy each area in their prime seasons. To make the voyage even more challenging, Sail OPO puts a novice crew aboard. So while moving a boat that you are not super familiar with you are tasked with training folks not accustomed to sailing offshore. The yachts spend a few days in Bermuda. I love being offshore making a sailboat operate at it’s peak efficiency. Be able to train some people to be comfortable offshore and to love the sport as I do is icing.

And we do sailing flotillas. Fellow circumnavigation (world’s youngest when in her teens) Tania Aebi and I run sailing trips in paradise. We choose an exotic destination, charter a few sailing yachts and spend a week exploring an interesting part of the world by sailing yacht. The sailing is laid back. Those who join can participate in the sailing as much or as little as they like. We are there to guide, teach, learn and enjoy. Our regulars are interesting, amazing people. Some sold their yachts as our trips grant them everything they are looking for.

And Sea Shepherd. Sea Shepherd gained some fame by risking the frigid Antarctic waters to put their little ships between whaling boats to stop the slaughters. And other achievements. I joined them when I learned that they were letting captains with less experience move their ships. My first trip with the US division was moving their first 110 foot Coast Guard vessel from Florida to California with a campaign in Sea of Cortez to save the Vaquita porpoise from extinction. It was awesome. I was captain on a boat with 16 of the nicest, environmentally conscious, animal loving humans that you would ever want to know. Though we got the small ship to Baja in record time, we had many adventures along the way. In Sea of Cortez we pulled illegal fishing nets and saved countless by-catch animals including the nearly extinct Tatoaba and Vaquita.

I love the ocean and moving boats efficiently. I enjoy being part of the education of our future sailing and/or ecology legends. Or just helping people enjoy the ocean and their own boats better. Interested people can reach me through our flotilla website, AdventureVoyaging.com or Fb.com/captainwoody.

We’d love to hear a story of resilience from your journey.

I didn’t see it as resilience at the time. I still think of it as my stubborn determination to not give up … with some resilience. It was one of my first longer international deliveries. My crew of two and I arrived in Belize to move a 40 foot sailboat to Florida. I had my dock friend with me. Carney was known for being a little crazy. For difficult trips, reasonably trustworthy crazy has value in that they don’t notice when a situation turns dangerous. And we had an older mellow Canadian that I got online. His value would come out later. We were picked up at the airport and whisked to a cool waterside local bar. “When are we going to see the boat?” was my question as drink two arrived. The owner answered, “We can check it out in the morning (day of departure), tonight we are having lobster dinner,” at their beautiful plantation home. Curious. We awoke to a beautiful day in Belize. We had had a world class dining experien
ce with the owner and his friends followed by a hilarious trip to town with the wives. The other side of my mind I started wondering, how bad is this boat?
The boat was not pretty on the outside. Inside it had no cushions and seemed to have been completely stripped. I never considered not doing the trip or ever experienced any kind of regret. I did ask what happened and they said that it was sunk in the last hurricane. “But the engine was running”. Even then I knew that running and making a long uphill (upwind) slog are two different things. We like to say that we experience 3 problems on boat deliveries: dirty fuel, dirty fuel, and dirty fuel. Fuel tanks must be maintained pristinely or they get growth and clog. I requested one thing, extra fuel filters, they gave us a few.
We had one clog on the way out through the reefs. We anchored and changed it. The next day we were out of filters and had to anchor behind a reef. We hired the guy with the car in the village to drive us 2 hours each way to a town with an auto parts store. We bought all of the inline fuel filters. Cut them into the fuel line. We changed filters every few hours, then every 12 hours, then less.
Upwind deliveries (aren’t they all?) can be trying for normal humans. The boat is on it’s ear (healing 40 degrees) for days at a time while it climbs each swell and bangs as it lands on the other side. This was where Carney showed his worth. I came out one watch and he had used a wrench to tilt the little BBQ the requisite 40 degrees, got it lit somehow and was BBQing steaks. Every wave we hit sprayed across the cockpit but he would hold his jacket open to block the grill. That kind of crazy. The Canadian had lots of offshore experience so he was fine. We enjoyed the hot meal, salted by the sea. The downside of crazy is that Carney kept pushing me to take the boat into Cuba. We were not laying (pointed toward) the only entry port of Havana so it was a hard no. Hours later, there was a banging on the deck above my sleeping head. I arrived on deck and asked, “Carney, what can I do for you?”. The wind had shifted a ton and when we tacked over, we were suddenly laying Havana. We spent the 24 hours of my birthday in Havana though 12 of that was doing customs, immigration, health etc. Still an amazing first Cuba visit.
We arrived in Key West to the surprise and accolades of the owners who had bet against us as we left the reefs of Belize.

What’s been the best source of new clients for you?

For our sailing flotillas, we prefer folks that are recommended by a friend that we have sailed with. I was able to acquire the email list from a sailing magazine that both Tania and I wrote and worked for. We don’t advertise at all :). Our list of readers are pre screened by having read years of our sailing adventures. And we have regulars who are addicted to our cruise format. We get the newest yachts based in the more exotic destinations. And have low key circumnavigators run them. Everything is provided once onboard. Every now and then someone not on our list reaches out. I have a phone conversation/interview. By the end I either recommend them to the ‘competition’ or invite them on our next Adventure. We are planning a Europe canal trip for next June (best way to explore Europe) and a sailing trip to the Baelerics of Spain, fall of 2024. And anyone can sign up for the Swan Program ocean deliveries. A much different kind of adventure.

Contact Info:

• Website: AdventureVoyaging.com
• Instagram: @captainwoody
• Facebook: /captainwoody
• Linkedin: /captainwoody
• Twitter: capwoody
• Youtube: @thecaptainwoody

Image Credits
Captain Woody Tania Aebi Lia Spinelli