A change in the wind!

Its been a while my friends and I would apologize, but I’m not going to. I will however share some things that have been brewing in the crew of Empiricus.

The past six years of my life, have been dedicated to completing a task, most arduous and that task is behind me now.

In 2010 when I decided to sail the northwest Passage, I lived alone on my boat, drifting I and out of relationships and spending as much time with my boys as I could, living in a place I did not want to be but making the best of it. Teaching sailing in Alaska for a few months and working construction in the winter wasn’t cutting it financially either. But I had my eye on a rescue plan if you will, for all of us.

I thought that if I planned something amazing, something huge, something beyond my reach. Then my sons would see the bright side, beyond the horizon of their home town. I dreamt of the three of us, crushing ocean on a round the world, homeschool, off grid, once in a lifetime voyage. Where we would all grow together, and perhaps even patch in, repair and heal our relationship, from all the time we lost when they were young…

Like the leader of a hike, they followed as directed. Then others joined in the hike and my dream, became alive in the hearts of others. So for so many reasons, I had to finish what I started, even when my sons wained of interest…

Samantha and I in Prins Christian Sound Greenland 2014
Samantha and I in Prins Christian Sound Greenland 2014

I was torn between the path ahead and the trail behind as the gap between us grew wider with each season.

The decision to complete the voyage, resulted in the most amazing, most rewarding but most financially challenging experience ever. So much was boiling inside me that by the time Samantha and I landed in Greenland, engaged to be married. The boil had reduced to a simmer and my pan was nearly dry. I was out of ideas on how to bring my sons into manhood with a global perspective.




As it turns out, the greatest benefactor from the voyage, was me. I met my wife in the arctic and pieced my life together with more purpose then I ever had. I also, I yielded to the process of making imperfect choices, day after day after day after day, while still having good intentions and good results.

In doing so, I learned, that like navigating in ice, being a father is more about moving in a general direction and controlling damage, then it is plotting an “ideal” course.

By the time, Samantha and I reached Iceland in the fall of 2014, I realized that my dream of exploring the world with my sons was not going to happen…

So how do we move forward? I had already showed them “it” can be done. When I say “it”, I mean anything one sets their mind to. But now what? I had planned to escape over the horizon in 2010 and now Samantha and I as a team are primed and ready for anything! But I am not done being a dad… So after the wedding we flew back to Alaska and moved back to Seward. The same port I had left behind forever…? Oh no… I sank into a funk,taking a job as a fish cannery/ refrigeration engineer, for less money then I made in high school. Slowly we started building our business of watching boats and making repairs building a good, but not quite sufficient client base to continue our circumnavigation.

You see, my plan for global exploration was never designed to return on an annual basis and start over. Holding a vessel in foreign lands and maintaining a life on land is a tall order. The fact we did it 3 years in a row was amazing. No, the plan was designed to stop along the way and work in ports in far off lands. Thats why the welder and extra tools onboard. All the planning, al the effort was aimed at that goal. Had it not been, I never would have made it…

So the current facts are, that the annual logistics of a piece by piece circumnavigation of the world while balancing a shared custody arrangement are not sustainable on a blue collar budget. Winter work in Alaska is slow for anyone who leaves in summer and since there is no flying in Seward for Samantha, we have been at the grindstone. Battling the reality of it all…

To top that, we just don’t see the point, in sailing away on a whimsical life vacation. That was never the point in the first place.  These are gifts to be shared.   So though I do believe, sailing the world would have been a rich experience for my sons and I do believe in finishing what I start. I just cannot finish it this way… So here we are… Boat in Iceland, building a business in Alaska.  Both attitudes best navigated in summer.  On one hand, my dreams of fatherhood and exploration together.  On the other, the only place where I can actually be… A father…

So whats the message? Ive struggled with this all winter. The message was this, “settling on a life you don’t want, is no way to live. But… If you are not around to pass on the good message to those who follow you, then the the lesson is lost in the wind”

This has been my winters quandary, a twisting message, indiscernible and fruitless. Needless to say, our theme since October has been Hard work and prayer, hard work and prayer, hard work and prayer… Prayer for what?  You ask. A magic solution? No. Rather Wisdom Purpose and opportunity… The results of those prayers… Astounding to be sure.

So without further delay, Samantha and I are proud to announce the next leg in our ocean journey as well as life. We have secured  “Salty” (a 65 foot Bruce Roberts steel hulled cutter, which Transited the Northwest Passage 2014 East to West) as an Alaska based, expedition charter vessel!

SV Salty, operating in Alaska.  www.sailwith7.com
SV Salty, operating in Alaska. http://www.sailwith7.com
Salty has a crows nest!
Salty has a crows nest!








The balance has been struck. No longer will we scrape cash for 9 months to sail for 2, while distancing the gap from my sons. No longer will we work, to sail. We will sail for work!

Seven Seas Sailing Logistics begin, EPIC level sailing charters beginning April 1st 2016.

So as of this moment, the mighty “EMPIRICUS” is for sale. She has been to me, what the enterprise was to Kirk. She is my blood, but like me, she was made to sail oceans, not sit on the hard. So if you’ve got big plans and moxie that requires a boat with the same, call me. Ive got an arctic equipped ship, waiting for you in Iceland.

Empirical at anchor amongst the bergs of Southern Greenland
Empiricus at anchor amongst the bergs of Southern Greenland

Oh man! there is so much to say and so much to do. We have a bone to chew on now and our skills have a place thrive. So for the next 3 years, while Steven is in High school and Isaac is off to college we will be right here. Right where I wanted to leave and somehow am now excited to be…. Here with My wife, my sons and the ocean at my feet…

There is a great work ahead!

Capt. Jesse Osborn


14 thoughts on “A change in the wind!

  1. Congratulations on your new trajectory, guys! Hope our wakes cross sometime this summer! We’ll stay in touch! All the best,
    Ellen and Seth
    s/v CELESTE

  2. Big, B-I-G, whale-ian, well-deserved congratulations on your new “Salty” adventure! …
    … from ‘SV Mandala’ a 34′ sloop, (one of Charley Morgan’s earliest) … on our return from a 3 month trip exploring the tropical cays & anchorages of the Exuma Islands … home originally to the peaceful Lucayan Indians (long since wiped out following Columbus’ landfall & “discovery” of San Salvador !)
    A multitude of mostly, uninhabited cays, pristine whitesand beaches & aquamarine waters … not unlike the Arctic really, except turtles passing by in place of seals; manatee (off Miami) in place of whales, oh!… & the water temperature … in mid 70’s!

    Photo: Swimming with pigs a Staniel Cay ~ where pigs come out from shore to beg food from passing boaters.
    The Tropic of Cancer cuts through Stocking Island, our southernmost anchorage but now, having crossed back over the 2000’+ deep Tongue of the Ocean & The Gulf Stream, now (motor) sailing northwards to homeport of
    Rev. Bob told me of his surprise at finding Empiricus on the hard at Reykjavik when he visited last Autumn.
    Incidentally I’ve passed on the fact that your beautiful Empiricus is for sale… to a pal, Dai Rice who is seeking a boat to replace ‘SV Catryn’ his 44′ Island Steampacket in which he had to turn back from Arctic Bay on his NWP bid in 2014, realising ‘Catryn’ wasn’t the ideal vessel. (Do you want to send me a resume for sale purposes, for me to forward onto him?)

    Wonder if you Samantha, found yourself saddle-back since your Arctic return – I recall your penchant for equine ventures.
    I look forward to meeting up with you seaboard again sometime in the future. Let me know your sail school plans & I’ll spread the word this side of the pond.
    Here’s wishing heath & happiness to you both … & the boys, from

    Stephanie…. sailing up sunny, east coast of Florida


    1. Thanks Steph its so good to hear from you! I will send the Empiricus info and am glad to meet any buyer in Iceland, to help them prepare. Sounds like your squeezing the joy out of life. Fantastic!

  3. That is AMAZING insight and writing Jesse!!! I’m anxious to watch this all unfold! What a cool thing to know you and Samantha.

  4. No matter what you all decide to do, it will no doubt be a success. Best of luck with the new adventure and we will be looking for you out there- can’t miss that big blue crows nest hauler. Hope you find someone to take Empiricus the rest of the way too!

    -Scott and Judie, s/v Sassona

  5. Waouhhh !!! 65 feet !!! Incredible Samantha and Jessie !!! All the best for all of you. We continue in Canada for the moment, and will sail back to Greenland in July, to winter there. Tell you more in an email
    Cécile et Phil

  6. We had the honor of meeting you guys at the Annapolis Boat Show when you spoke with Matt Rutherford. I still have your business card on my desk as a reminder that your dreams of sailing can come true. I admire you guys so much and remember you talking about your commitment to your family. Congratulations on finding a way to be a father and as you say, “sail for work”. I am sure this will be a great endeavor and I hope one day in the next three years we can come up and sail with you. Thanks for sharing your story!!

    Jim and Helen
    SV Luna Sea Chesapeake Bay

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