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David Cross // The Loan Sailor

On the Wind Sailing

Release Date: 01/28/2025

Matt Rutherford // A Near-Sinking En Route to Bermuda show art Matt Rutherford // A Near-Sinking En Route to Bermuda

On the Wind Sailing

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. -- ON THE WIND is presented by Forbes Yachts, the yacht sales professionals. Forbes Yachts sell the boats that allow you to effortlessly...

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Jesse Terry // Sailing & Racing a Classic Wooden Boat show art Jesse Terry // Sailing & Racing a Classic Wooden Boat

On the Wind Sailing

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. -- ON THE WIND is presented by Forbes Yachts, the yacht sales...

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Paul Osborne // Sailing Around the World for Down Syndrome show art Paul Osborne // Sailing Around the World for Down Syndrome

On the Wind Sailing

Paul Osborne is the dad behind . 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. -- ON THE WIND is presented by Forbes Yachts, the yacht sales professionals. Forbes Yachts sell the boats that allow you to effortlessly connect...

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Don McIntyre Returns // OGR Founder & Philosophies on Sailing & Adventure show art Don McIntyre Returns // OGR Founder & Philosophies on Sailing & Adventure

On the Wind Sailing

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. -- 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,...

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Peter Gibbons-Neff // Completing the Mini-Transat show art Peter Gibbons-Neff // Completing the Mini-Transat

On the Wind Sailing

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! -- ON THE WIND is presented by Forbes Yachts, the yacht sales professionals. Forbes Yachts sell the boats that allow you...

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David Cross // The Loan Sailor show art David Cross // The Loan Sailor

On the Wind Sailing

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. -- 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...

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Andrew Hesketh // Corporate to Cruiser show art Andrew Hesketh // Corporate to Cruiser

On the Wind Sailing

Andy Hesketh, aka Andy H. is the founder of the 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. -- 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...

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Andy & Mia // 2024 Year-in-Review show art Andy & Mia // 2024 Year-in-Review

On the Wind Sailing

Happy New Year podcast listeners! Mia & I are back with our somewhat-annual year-in-review show, where we sit down and chat through the highs and lows at 59º North. This one was recorded onboard FALKEN just before the first trip of 2025 was set to depart Portugal. Mia & I discussed everything from new projects coming in 2025 to the successes (and failures) of 2024 as well as our plans as a sailing family. 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...

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Lin Pardey & David Haigh // Cruising Memories show art Lin Pardey & David Haigh // Cruising Memories

On the Wind Sailing

Lin Pardey is a living legend, having paved the way for countless cruising sailors for her epic voyages in an engineless boat with her husband Larry in the 60s and 70s, beautiful boats they built by hand, by themselves. Now at 80 years old, she's still doing it. I sat down with her and her new partner David Haigh, himself an accomplished solo sailor in Annapolis to talk about life after Larry and what inspires her and David to keep forging new sailing memories. Click here to support and purchase Lin Pardey’s 2024 book, Also by Lin Pardey in 2024:  -- ON THE WIND is presented by Forbes...

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Gurra Krantz // Över Atlanten TV Show show art Gurra Krantz // Över Atlanten TV Show

On the Wind Sailing

Gurra Krantz returns to the podcast to talk to Andy about life after the Whitbread Race. What do you do after sailing 4 laps around the globe at the highest level of the sport!? Lots, apparently. Gurra talks about his involvement in the hugely popular Swedish TV series 'Över Atlanten,' about his lack of philosophy when racing offshore, motorboating, marina ownership and more. . -- 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...

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More Episodes

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.

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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.

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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.