In some ways the highlight was talking to the crew - Jesse and Samantha - 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 Jesse and Samantha Osborn, 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. 

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 12 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, 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. 

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.

Both Samantha and Jesse have 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.

Jesse and Samantha are ready to take you exploring!

Jesse and Samantha are ready to take you exploring!


ok, that's all great...but can they cook?

When they're not making high latitude voyages or delivering sailboats, both Jesse and Samantha love to cook and eat. Both have taken numerous culinary classes over the years. Jesse's specialities are fine sauces in the French tradition, paired with fresh Alaskan seafood. Samantha bakes and cooks a wide variety of foods, preferring fresh, local ingredients for making classic, unfussy but delicious fare. Indian, Asian, Mexican and North African flavors color the menus aboard Extraordinary.