#250: Matt Rutherford and Randall Reeves are both veterans of the podcast and extremely accomplished single-handed ocean sailors. In today's special episode, Matt guest-hosts the show to talk to Randall about his latest attempt at the 'Figure 8' voyage, his plan to sail solo and nonstop around the America's AND Antarctica. Randall was on the show with me just before his first attempt, which failed when he suffered a serious knockdown, blowing out the windows in his boat's wheelhouse. At the time of this recording with Matt, Randall was set to depart San Francisco on his second attempt the very next day; just this week, Randall rounded Cape Horn. This episode first appeared on Matt's own show  "Single Handed Sailing," available on  iTunes and wherever else you get your podcasts. Matt's a world-class story-teller - his podcast is great! -- On the Wind is presented by Rutgerson Marin. And also supported by Offshore Passage Opportunities.

Matt Rutherford & Randall Reeves // Figure 8 Voyage Solo, 2nd Attempt

The definitive podcast about sailing. Professional sailors Andy Schell, Emma Garschagen, and August Sandberg interview sailors from around the world to discover what motivates, scares & inspires them. For over ten years and through 400+ episodes, our hosts have interviewed sailors like Dee Caffari, Sir Robin Knox-Johnston, Liz Clark, John Kretschmer, Kirsten Neuschafer & many, many more. We talk to boat builders, yacht designers, YouTube stars, performance racers, and many more. HOLD FAST!

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Suzanne Heywood was raised on a sailboat. What started as a three year circumnavigation with her family turned into a decade of living aboard, sailing, and struggling to get an education. Suzanne's book, 'Wavewalker,' tells the story of that voyage. In this episode, Emma and Suzanne talk about 'Wavewalker,' Suzanne's relationship to sailing now, and her thoughts on giving kids an unconventional upbringing. -- If you liked this conversation you'll LOVE The QUARTERDECK, 59 North's 'deep dives on the art of seamanship.' Join our interactive community and get involved in the conversation at quarterdeck.59-north.com. First two weeks FREE, then multiple pricing options thereafter.  -- ON THE WIND is presented by Forbes Horton Yachts. Get in touch with Forbes today about buying or selling a boat. The show is also presented by Harborburn Cannon Company, creators of solid, marine-grade bronze, black-powder signal cannons — just like the ones from the age of sail but a bit smaller. If you own a boat, you need a cannon! To find out more, go to harborburn.com.

Suzanne Heywood // Wavewalker: Breaking Free

Alex Laline is a lifelong sailor and one of our full-time staff at 59º North. Growing up in a multinational family, he sailed dinghies as a kid in the UK, Spain and Indonesia, then got inspired to sail around the world when he saw an ad for the Clipper Round the World Race. As a teenager he saved all his money and joined Clipper as a paying crewmember, completing a circumnavigation and later going on to work as a mate and now skipper for them as well, under the guidance of Clipper founder Sir Robin Knox-Johnston. I talked to Alex about his career onboard FALKEN in Barbados. -- If you liked this conversation you'll LOVE The QUARTERDECK, 59 North's 'deep dives on the art of seamanship.' Join our interactive community and get involved in the conversation at quarterdeck.59-north.com. First two weeks FREE, then multiple pricing options thereafter.  -- ON THE WIND is presented by Forbes Horton Yachts. Get in touch with Forbes today about buying or selling a boat. The show is also presented by Harborburn Cannon Company, creators of solid, marine-grade bronze, black-powder signal cannons — just like the ones from the age of sail but a bit smaller. If you own a boat, you need a cannon! To find out more, go to harborburn.com.

Alex Laline // Clipper Round The World Skipper

Sailing was never a part of Lutz Kohne’s life growing up — it hit him square in the face as an adult, and completely changed his trajectory. He has since worked as a professional skipper, as Race Director for the OGR and the GGR, and he is now preparing to set sail himself, around the world, solo, retro and unassisted as a participant in the Golden Globe Race 2026. -- If you liked this conversation you'll LOVE The QUARTERDECK, 59 North's 'deep dives on the art of seamanship.' Join our interactive community and get involved in the conversation at quarterdeck.59-north.com. First two weeks FREE, then multiple pricing options thereafter.  -- ON THE WIND is presented by Forbes Horton Yachts. Get in touch with Forbes today about buying or selling a boat. The show is also presented by Harborburn Cannon Company, creators of solid, marine-grade bronze, black-powder signal cannons — just like the ones from the age of sail but a bit smaller. If you own a boat, you need a cannon! To find out more, go to harborburn.com.

Lutz Kohne // Golden Globe Manager turned Racer

Henry Mickle & Bayley Richardson are self-described "Mates from the Land Down Under", cruising around the world in an old Beneteau. These two twenty-something friends made a pact, worked their asses off, saved their money, bought a boat and are living the dream — figuring it out as they go, but with knowledge and experience earned from working professionally offshore in Australia's oil industry. I spoke to them onboard FALKEN on anchor in Barbados about the wild highs and scary lows of their adventure so far in their mission to sail REVELRY home to Australia. -- If you liked this conversation you'll LOVE The QUARTERDECK, 59 North's 'deep dives on the art of seamanship.' Join our interactive community and get involved in the conversation at quarterdeck.59-north.com. First two weeks FREE, then multiple pricing options thereafter.  -- ON THE WIND is presented by Forbes Horton Yachts. Get in touch with Forbes today about buying or selling a boat. The show is also presented by Harborburn Cannon Company, creators of solid, marine-grade bronze, black-powder signal cannons — just like the ones from the age of sail but a bit smaller. If you own a boat, you need a cannon! To find out more, go to harborburn.com.

Henry Mickel & Bayley Richardson // Sailing REVELRY Home to Oz

Jojo Pickering grew up with sailing as a central part of her life, vagabonding on the high seas with her family and sailing from Africa to the UK. As she got older, she spent more time ashore, starting a traveling theatre company with her husband and kids and bouncing around the UK, France and Spain. But the sea called her back — she recently completed an Atlantic circle with her family on a gaff-rigged sloop and now sails professionally as a skipper on classic yachts and with 59º North. Andy spoke to her onboard FALKEN in the Cape Verde islands. -- If you liked this conversation you'll LOVE The QUARTERDECK, 59 North's 'deep dives on the art of seamanship.' Join our interactive community and get involved in the conversation at quarterdeck.59-north.com. First two weeks FREE, then multiple pricing options thereafter.  -- ON THE WIND is presented by Forbes Horton Yachts. Get in touch with Forbes today about buying or selling a boat. The show is also presented by Harborburn Cannon Company, creators of solid, marine-grade bronze, black-powder signal cannons — just like the ones from the age of sail but a bit smaller. If you own a boat, you need a cannon! To find out more, go to harborburn.com.

Matt Rutherford & Randall Reeves // Figure 8 Voyage Solo, 2nd Attempt

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