In some ways the highlight was talking to the crew... who had tales about sailing the north-west passage and bush pilot escapades in the Canadian arctic. But the views and the food were both excellent.
— 2016 guest

Meet the Crew:

You're in good hands with the crew of Extraordinary.  Their combined skills form a uniquely qualified team that can sail you confidently into some of the world's most remote places. 

 Approaching landfall in Greenland, summer 2014 on  S/V Empiricus. 

Approaching landfall in Greenland, summer 2014 on S/V Empiricus. 

Captain Jesse Osborn has been an Alaska resident since 1987. He is a licensed USCG Captain, ASA sailing instructor and PADI Divemaster. Working as a delivery captain, he's logged more then a dozen trips across the Gulf of Alaska, in all seasons, and five Inside Passage deliveries on the west coast of North America between Alaska and Washington.

Between charters, Jesse works as a sailing instructor and marine mechanic, teaching everything from Sail repair, to storm tactics and celestial navigation. In 2011, he was voted Sailing Instructor of the Year by the American Sailing Association.

 Prior to purchasing Extraordinary, he sailed through the Northwest Passage during the summers of 2013 & 2014.

It was on this voyage, in an isolated hamlet in the middle of the Canadian Arctic, where he met Samantha. 

First Mate/Chef Samantha Osborn is a Canadian-born commercial pilot with 20 years of Arctic experience exploring and flying professionally in Canada’s high latitudes. Samantha’s flying experiences in the high arctic make her very comfortable operating in remote and isolated environments. This competence landed her a job flying a Dornier 228 in Indonesia and a Turbine Beaver in the Canadian arctic. The latter job brought her to Cambridge Bay, Nunavut, in 2013, where she met Jesse. In 2014, she joined Jesse in the Canadian Arctic and they sailed his 19 ton, gaff-rigged sailboat, Empiricus, to Greenland. In 2015, the pair sailed down the west coast of Greenland and across the North Atlantic to Iceland.

Read about their voyage through the Northwest Passage here.

Deckhand/kayak guide Ryan Middleditch joins the Extraordinary crew in the summer of 2018. Originally from Michigan, he left for warmer climates and found work guiding kayak trips in the warm tropics of Kauai. After five years in Kauai, he wanted something different, and found himself guiding guests at a remote wilderness lodge in the Kenai Fjords National Park, Alaska.  It was here that he met Jesse and Samm. Ryan has seven years of guiding experience, has his Level 2 Coastal Kayak Certificate through the American Canoe Association, and is a certified Wilderness First Responder.


All of the crew have wilderness-specific first aid training and survival training. During their varied careers they both have had the opportunity to practice these skills in real world scenarios.

These experiences and skills lend themselves to remote operations and self-sufficiency, key components in providing both safe and interesting experiences to you.

Tico, our sailing dog, loves to greet our guests and make them feel at home aboard Extraordinary. He has sailed across the Gulf of Alaska and joins us on our charters. He is a very proud West Highland Terrier. He is low-key and hypoallergenic. 

 Tico on a skiff ride. 

Tico on a skiff ride.