On the Wind Sailing

Latest Episodes:

Ben Doerr Returns // Sail Bainbridge Apr 15, 2025

Show notes

Ben Doerr, longtime friend of the pod and founder/skipper at Sail Bainbridge in Seattle, returns to the show to spin some yarns with Andy. This episode is really a catch-up between Ben & Andy, who haven't spoken in a while, and is a wide-ranging episode on everything from sailing & skiing in Alaska to being away from home when you've got a young family. We also briefly touched on Ben's new Sail2Run project in the San Juan Islands. Check out Ben on sailbainbridge.com.

This season of ON THE WIND is sponsored by Weather Routing Inc., aka 'WRI', 59º North's longtime weather routing & forecasting friends. To learn more and sign up for WRI, go to wriwx.com and tell them that 59º North sent you.

This season of ON THE WIND is also sponsored by Boat How To, an educational website co-founded by longtime friend of the pod & sailing tech guru Nigel Calder. Check out the courses at BoatHowTo.com.

Louay Habib // The Master of Sailing Media Mar 18, 2025

Show notes

Louay Habib is a true sailing insider. Everyone who participates regularly in any of the major offshore races around the world will know Louay. In fact, if you yourself follow sailing – say races like the Fastnet, the Ocean Race - you probably know Louay too – well his writing at least. Currently he is the communications manager at the Royal Ocean Racing Club. But for two decades, Louay has reported on sailing. He is a master in conveying the drama and passion of the sport – to both sailors, and non-sailors. I figured, someone who has been so deeply embedded in this industry for so long must have garned some wisdom and insider knowledge worth sharing. I hope you enjoy.

ON THE WIND is presented by Forbes Yachts, the yacht sales professionals. Forbes Yachts sell the boats that allow you to effortlessly connect your passion for yachting to the sea, bringing your world one step closer to perfection. Visit forbesyachts.com to get in touch.

ON THE WIND is also supported by Boat Doctor, powering life on the water. Boat Doctor designs high-powered, off-grid energy systems for boats, RVs and other off-grid applications. To find out more, go to boatdrusa.com.

Katy Campbell // Founder of Sea to Sky Sailing School Mar 11, 2025

Show notes

Katy Campbell is a world-class sailor, groundbreaking entrepreneur, and one of my lifelong friends. A decade ago, Katy launched her sailing school 'Sea to Sky Sailing'. Sea to Sky is now the only RYA-recognized training center on North America's west coast, and Vancouver's only school offering both cruising and racing programs, including a regular winter Caribbean race circuit which is where we recently got together to record this podcast. Google Katy, and the title: "Dinghy Sailor Turned Keel Boat Goddess" comes up. Yes, she really is a goddess, a wonderful friend – and as you are about to find out – a trail blazing source of inspiration for any of you who dream of carving your own adventurous path in this world.

Matt Rutherford // A Near-Sinking En Route to Bermuda Mar 04, 2025

Show notes

Matt Rutherford returns yet again to the podcast, this time from his outpost in the Philippines. It's always fun to catch up and shoot the shit with Matt, but this time I really wanted to hear about his near-sinking on a Caribbean delivery last fall. Matt talks through the entire ordeal, from riding out a gale with all the pumps running, to nearly losing the rudder out of the bottom of the boat, to ultimately his safe landfall in Bermuda.

Jesse Terry // Sailing & Racing a Classic Wooden Boat Feb 25, 2025

Show notes

Jesse Terry is a normal guy — dad and husband, keeps a 9-5 job, lives in the city, etc etc, all that "normal" stuff. But he's decidedly not normal as a boat owner — keeping a classic wooden ketch in top condition with some friends and racing & cruising her up and down New England's coast and out to Bermuda. I talked to him about the contrast between his "normal" life and sailing life, what it's like owning a wooden boat and a recent heavy-weather Bermuda Race which saw a few major incidents at sea.

Paul Osborne // Sailing Around the World for Down Syndrome Feb 18, 2025

Show notes

Paul Osborne is the dad behind Osborne Adventure. Paul's family, including his wife and three kids, are planning a unique circumnavigation over the next few years to raise awareness for Down Syndrome. Paul has spent a lifetime traveling, mountain biking, white water kayaking, climbing, camping, and hiking, and in real life is a photographer and designer. I spoke to Paul about his adventure planning, life with kids, being a dad, sailing and much more.

Don McIntyre Returns // OGR Founder & Philosophies on Sailing & Adventure Feb 11, 2025

Show notes

Don McIntyre, founder of the GGR, OGR and now MGR, returns to the podcast! Andy sat down for a meandering conversation where they talk about meeting in Lagos, Portugal at the start of the Mini Globe Race, his philosophies on life, sailing and adventure, Don's definition of success, how he handles the 'haters' surrounding his ambitious events, how he pays for his crazy ideas and lots, lots more.

Peter Gibbons-Neff // Completing the Mini-Transat Feb 04, 2025

Show notes

Peter Gibbons-Neff returns to the podcast to talk about the successes and failures of his Mini-Transat racing campaign. "PGN" and I sat down face-to-face in Annapolis where he told me about losing a rudder shortly after the start in the Canaries, the hardest part about solo sailing a 21-ft. boat, how the mini-class doesn't allow even basic electronics, his military background and how that helps him offshore — plus his plans to one day win the Mini-Transat! https://www.pgnoceanracing.com/blog

David Cross // The Loan Sailor Jan 28, 2025

Show notes

David Cross is an author in the midst of writing a book — a large portion of which involves a solo, offshore passage to Brazil. Wanting to get the fundamentals right, David asked if he could turn the tables and interview me about this fictional voyage in order to make it as realistic as possible. Of course I was happy to oblige, and this conversation is the result of our chat. Read more about his book on loansailor.com.

Andrew Hesketh // Corporate to Cruiser Jan 21, 2025

Show notes

Andy Hesketh, aka Andy H. is the founder of the Odyssey Sailing Festival and host of the Ocean Cruiser's Podcast. Andy lives aboard his Jeanneau Sun Odyssey called VOYAGER and has been sailing full-time for several years. He wasn't always a sailor though, leaving a corporate life behind to pursue wider horizons. I talked to him last fall when he was aboard is boat in Greece.

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