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What started as a plan to sail to the Kailani from California to Hawaii evolved into friends on an explorer's journey to some of the most remote places on the planet

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Rusty is the captain and owner of Kailani. A lifetime on oceans across the globe, Rusty started early out of Annapolis, MD, long distance ocean sailing as a kid around the Atlantic on a Tartan 30. He spent much of his adolescence racing, cruising and delivering boats up and down the east coast. He graduated from Maine Maritime Academy, working merchant marine on tankers both as crew and an engineering officer. In 2002-2003 he and his awesome ex lived on a small sailboat for a year in the outer Bahamas and the Turks&Caicos. Returning to sailing with the purchase of Kailani in 2014, he started her out with the sail from Portland, OR to San Diego. Since then she has run 4,957 nautical miles, including a lot of time in the channel Islands, prior to this trip. When not sailing Rusty has one job at the moment, to be a proud parent to his great kid, Starry. When not at sea Rusty lives in Jackson, WY and Ririe, ID.

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Kevin Ryan has been sailing since his early teens. Raised in Southern California, He pursued racing, sail instruction and skippering yachts in the charter, delivery and passenger services early on in his life securing a 100 Ton captains license at 20. Many deliveries followed to include transits from Florida and Texas to the British Virgin islands.


A pivotal moment in his early twenties introduced Colleen, his wife of 29 years and changed the course of his life. Moving to Chicago to begin a life with Colleen changed Kevin’s focus to the yacht service and systems side. The Great Lakes brought new sailing and racing experiences.


Josh’s passion for travel was was fueled at an early age by family vacations and expanded as he aged through his love of adventure tales in film and literature. He left his Michigan roots for college and eventually migrated to northwestern Wyoming where he now resides with his son, and spends time hunting, fishing snowboarding, and mountaineering. Kailani 2021 marks Josh’s first foray into sailing and he is excited to learn the art and add his skills and enthusiasm to the team. 

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Brian McVickers has been sailing since age 12 and has accumulated approximately 35,000 nautical miles racing and cruising on a variety of different boat designs. Racing for Columbia and Chicago Yacht clubs through his high school years he went on to race for Old Dominion University throughout college, compete in national championships and 10 Chicago to Mackinac races. As a sailing instructor and racing coach he worked for both Columbia and Chicago Yacht clubs and headed the Waukegan Yacht Club sailing program for four years. 

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Kailani, an Island Packet 485 was born in 2007 in Florida. She is 51’ 6” and weighs in at around 55,000 pounds fully loaded. She lived the first part of here life named Faith, languishing in St Helen’s, OR and mostly unused. She was acquired and renamed in 2014 and a few months later made the trip down to San Diego. She has spent considerable time in the Channel Islands prior to being completely refit for Arctic exploration. She keeps us safe and keeps driving ahead.

First Leg Crew


Scott is the publisher of and Overland Journal. His travels span all seven continents and includes three circumnavigations of the globe. His polar expeditions include two vehicle crossings of Antarctica and the first long-axis crossing of Greenland. @scott.a.brady

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