134: Jesse & Samantha Osborn

Happy New Year! Welcome to the first episode of 59º North in 2016! 

Episode 134 is Jesse & Samantha Osborn. You won’t have heard of them, but they’re some of the most interesting and accomplished cruising sailors I’ve ever come across. Matt Rutherford introduced me to them last fall and they ended up sleeping aboard Isbjorn during the week of the Annapolis Boat Show, bunk-mates with the legendary Don Street, who also took up residency aboard. Jesse & Samantha sail a one-off, steel-hulled gaffer called Empiricus and recently completed the Northwest Passage, and only just, narrowing avoiding getting frozen in for a long winter. Empiricus remains hauled out in Iceland, where they’ll be continuing their adventures in the Arctic next summer. Amazingly, the couple had little prior sailing experience before their adventure in the Arctic.

In the offseason, Jesse & Samantha live a sort of home-steading lifestyle in Alaska. Samantha is a veteran bush pilot, flying into and out of remote regions in Arctic Canada on float planes and ice planes, providing supplies to wilderness communities. Jesse is a former police officer and has since given that up in pursuit of his dream to live simply on the water and off. They started and run Seven Seas Sailing Logistics, a self-declared ‘sailing concierge, with the goal of helping others achieve their bluewater dreams.

Samantha & Jesse are also young, and I always get extra excited speaking to sailors in the up and coming generation, and these guys are super inspiring. A favorite quote I discovered on their boat’s website, empiricusembarks.com states “IF YOU DON’T WANT SOMETHING, YOU MAY SETTLE FOR ANYTHING. BUT ANYTHING, COULD BE NOTHING AT ALL.” It pretty well sums up their dreams and ambitions. 

This episode was recorded during a break I had at Cruiser’s University in Annapolis last October, and about a third of the way in, Pam Wall pops into the conversation as a surprise special guest! Pam had asked to listen in on the conversation as we recorded. I think she meant to remain off-mic, but Jesse & Samantha’s stories were so compelling that she couldn’t resist asking them some questions of her own. It was truly inspiring watching Pam, a legend of her generation of cruisers, interact with us up-and-coming younger sailors and seeing her eyes light up at Jesse & Samantha’s stories. It was a real honor having Pam sort of co-host this episode.


Thanks to everyone who answered the call to donate after the bonus ‘Money’ episode, in particular longtime listener Pedro for his generous gift. If you'd like to help support the show and Isbjorn Sailing, visit 59-north.com/shop to buy some small-batch gourmet Oh Dark Thirty coffee, an Isbjorn Sailing t-shirt or simply donate to the podcast. Of course a nice email is always welcome, as are reviews on iTunes. Thanks to all of you for the continued support. Both Mia and I wish you all a happy and healthy 2016!


This episode is sponsored by 59 North – yep, that’s Mia and I again. 2016 is our first year with a full calendar of ocean passages scheduled aboard Isbjorn – that’s Swedish for polar bear, by the way – our classic Swan 48. We’re sailing nearly 10,000 miles this year, including an Atlantic crossing via Nova Scotia, Newfoundland & Ireland that will re-trace the route we took on Arcturus back in 2011. The trips are filling fast – we take four crewmembers per passage who complement Mia and I – and the price includes all onboard food, drinks, PFDs & safety equipment. As of this recording, we only have nine crew bunks left for the year – Trinidad-BVI in February, Key West to Annapolis in April, Halifax to St Johns, Newfoundland in July and Kinsale, Ireland to Lisbon in September. 

“All men dream,” wrote TE Lawrence, “but not equally. Those who dream by night in the dusty recesses of their minds, wake in the day to find that it was vanity: but the dreamers of the day are dangerous men, for they may act on their dreams with open eyes, to make them possible.” 

Join us this year on Isbjorn and fulfill your ocean sailing dreams. Visit 59-north.com/offshore to view our calendar and register to sail with us.

Show Notes 

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