Jesse Osborn started sailing in 2006, when he was transferred to Ketchikan, Alaska for his job. He purchased a 50’ sailboat, Empiricus. Over the next 10 years he sailed this gaff-rigged yawl from Alaska to Ireland, while also starting Seven Seas Sailing Logistics, delivering many boats across the Gulf of Alaska and up and down the Inside Passage. You can read about his voyage through the Northwest Passage here: www.empiricusembarks.com

Jesse spends his time writing, coaching and teaching sailing. Both he and Samantha sail their own boat, Empiricus, together. Currently Empiricus is in Ireland and she’ll make her way to the Azores in 2026.

Samantha Osborn started sailing on her own boat, a Kirby 25 named Knot Krazy, in 2011. When she met Jesse in 2013, she hadn’t dropped the anchor or stayed out overnight on her boat. That all changed the summer of 2014 when she joined him for the continuation of his Northwest Passage voyage. She has been sailing regularly since then and has now logged over 10000 ocean miles. When she’s not sailing with Jesse, she works as a medevac pilot and rides her Arabian horses.