Jessie (Me. Hi.) Desireé (Sailboat) Luke (Fiancé)

Me and them. Him, her and I. Myself, she and he. Us and him. Them and me.

Here we are. Two girls, one boy.

I’m sitting here at my desk in Northport, Michigan. Seven inches of winsome snow lay on my deck, and they accumulate quicker than I can sort out what my next sentence will be. Luke, the man I agreed to marry, sits opposite me and researches the point at which icebergs shouldn’t be a concern in crossing the North Atlantic Great Circle Route. I’ve had my fear on boats; adding icebergs to the list doesn’t appear to be deterring my hunger to cross oceans.

It’s been just over two years since Katie Smith and I completed America’s Great Loop aboard S/V Louise. I’ve spent my adulthood making abrupt life changes in two year stints. Whether it was where I was living, what I was studying, who I was dating, or where I was adventuring – in reaching two years, some kind of fervent curiosity always led me elsewhere. Every time. By no means has this been a conscious countdown…it’s this uncontrollable enthusiasm to do, to see, to be, more than whatever I was, whatever I am.  I’ve been back home in Michigan now for… just over two years.

Staying put has always been my most difficult task. If you were to query my  multiple employers they certainly wouldn’t categorize my actions as “staying put”. However from my perspective these past two years have been my safest. My most grounded. My most sensible. But here I am again uncontrollably enthused about not just one, but two of my finest decisions. The first one joyously shattering my two year stints, and the second one holding me right to schedule.

  1. I said yes to forever. I do not understand what forever means. I don’t think many of us do. But I have discovered who I want to try and understand that with. Who I want to work for that with. Who will freak out every two years with me, dropping everything, most likely to attempt something for which we are completely unqualified.
  2. So what now?  Our first test is an obvious one: to plan a sailing trip instead of a  wedding. We will sail double handed from my country to his. America to England. It only seems practical for us to sign up for the first “forever” test.

As the list begins of how we can possibl pull this off by spring, I have ransacked Luke’s notes with full intentions of relaying them to the world without his permission. So here they are… Luke’s unedited notes followed by my italicized assessment of course.


Who’s boss? Well that’s obvious – who is legally responsible? You’d think that’s “the man’s job” but technically the boat is Jess’s and her sister’s inheritance. So she is the captain. This is correct, Smart man. I could be considered a co-skipper.


6000 nm “America’s Great Loop” with another sea-bird called Katie, aboard a 27 foot Cal called ‘Louise’. Made famous by their mildly entertaining blog, articles in Cruising Outpost and on Sailing Anarchy. Two landlubbers on a learn or die mission to sail the inland waterways and Eastern seaboard of the United States of America. Including Bahamas and Canada. They made it, and came home with two years  of quality live-aboard experience. 60% coastal cruiser, 40% adventurer, 0% racer. 


Sailing everything and everywhere since 1995. 60% Racer, 40% adventurer 0% cruiser. Sailed an 18 ft catamaran double- handed 2000 nm around Great Britain because he was bored of sailing up and down the coast. Humbly not mentioning he holds a speed record for sailing  around Britain. Later sailed a 1937 wooden 15 sqm 1700 nm from the UK to Sweden for fun. Enjoys difficult situations. Likes to keep the spinnaker up too long. Thrives on danger. Has the oddest sense of humor.



1962 Pearson Invicta 37′ ketch designed by Bill Trip Jr. Yawl. Owned by Jessica’s father Jim Wizard ( his pride and joy for decades ). Old fashion shallow draft long keeler with centerboard designed for CCA rules. I don’t know what CCA means. Won the 1964 Newport to Bermuda race. Heavily built. First GRP boat to win this prestigious race. I don’t know what GRP means either…racing stuff.  There are 20 of these hulls in existence. It has made 4 Atlantic crossings in it’s time. Our hull, No. 8, has not seen the salt water since 1975-ish. It is in pristine condition and it will be expected of me to keep it this way. AH. 



Recently engaged couple attempts their first ocean crossing of the North Atlantic, sailing the great circle route double handed across the Atlantic is considered tough, very tough. It’s a long way north, its cold, its wet, and its windy. The dangers are everywhere, Atlantic storms, icebergs, huge seas, container ships, and potential Hurricanes. Sleep deprivation from being on watch becomes debilitating, even crippling as the days pass. Tempers will fray. Will this transatlantic leave their happy engagement in pieces or will they overcome the odds and become crew mates for ever. Dun dun dun.  

pilot-chartAnd there you have it. We are both making light of this situation when it is in reality quite heavy. Poking fun at a serious quest is really the only way I know how to manage the highly overwhelming preparation.  Luke and I are taking on this responsibility seriously and have a full understanding of the threats it poses, the impact it will have on our families, and on our relationship. This colossal trial will test many things aside from young love. And for some unknown reason I have my head wrapped tightly around this possibility, just as the average 27-year-old would have around her wedding. What’s wrong with me? I am consumed. I am hyper. Keen – as Luke would say.

We are not being funded in any way and are not trying to be funded. Expenses are coming from what I have been able to save over the last several years and from what Luke will be contributing from his salary as the own label manager for Hyde Sails. We are blessed to have a solid, ocean worthy boat to borrow and if it weren’t for that we would be a long way from the ability to pull this off on such short notice. Narrowing down the list of prep-work and separating wants from needs has be tricky. Here is what we are left with :




  • JORDAN SERIES DROGUE (or something similar) 






If you have any of this stuff laying around, know someone who might, or if you have good contacts for any of these items please email me. If you have something else laying around you firmly believe is a need not a want / are interested in selling, email me. We would like to keep things simple as possible, bringing only the items that may help save our lives if and when we find ourselves in a sticky situation.

I welcome advice, direction, and any kind of feedback as we spend the next few months running around with our heads cut off. ANYTHING HELPS. I will be blogging about the process as well as writing articles for Cruising Outpost & Sailing Mag.

WOOOOOO !!!! ! ! ! ! !   !   !    !     !       !        !          !            !              !

Thank you for finding yourselves at this “mildly entertaining” blog once again. I promise to keep the content provided honest, authentic, and as relatble as possible. I understand these kind of voyages can be difficult to wrap our minds around. Those of you who make it to the end of these posts are those who keep me motivated. XO.

56 thoughts on “Two Girls One Boy

  1. Sounds so exciting! At least mildly entertaining…;) I’m 37 and I’ve been married for 18 years, while I’m not a sailor [yet], I can tell you that marriage is riding waves, recognizing currents, navigating storms, and a lot of dirty, hard work. You’re going to get some amazing practice.

  2. I have enjoyed your writing since first found your circuit blog. I am thrilled for both of your new adventures and look forward to your posts. Make yourself a You Tube channel, and look into Patreon. See Sailing SC La Vagabonde and Sailing SC Delos!

    1. Thanks for stickin around David ! I’ve seen many of their entertaining videos… we will see if I tap into the whole youtube channel thing. To be honest my heart lies in photography, believer that a good photo can say the same things a video could. On the flip side, I had a blast making ridiculous videos with Katie in the past…

  3. Hi. Long time reader, first time poster. Sounds like it will be one h*ll of an adventure. Look forward to reading about it.


  4. That sounds amazing and scary! I’m so excited for you and looking forward to hearing all about it in your blog.

  5. Congratulations! And the plan comes together! I’m excited for you both and I believe this will be just the beginning! (in more ways than one!)

  6. Looking forward to following along.
    Met you and Katie in Killarney, Ontario..!
    GRP= Glass Reinforced Plastic (Fiberglas).
    Safe travels..!!

  7. FYI — “CCA” stands for Cruising Club of America, an august, old-line sailing club. The CCA produced a rating rule for sailboats many years ago, and your Pearson was designed to conform to the rule. The CCA rule tended to produce hulls and rigs that were seakindly, well behaved, and reasonably fast. I doubt you will think the Pearson is fast at all, but if you sail into a patch of bad weather on the TransAtlantic, you may end up blessing the old, solid, CCA-rule Pearson.
    GRP is even easier — it stands for Glass Reinforced Plastic, it is simply another term for what we call fiberglass.

    I look forward to future posts.

  8. You’re a bonafide badass. Hoping you and your fiancé get everything you need as soon as possible. Looking forward to following your adventures.

  9. Very exciting! Your sense of adventure is awesome and I admire your “just do it” attitude. Having crewed with my wife of just over one year on a sailboat from Hawaii to Alaska last summer, I can tell you it will all be worth it! I look forward to our next voyage, hopefully on our own boat.

    Have you considered heading north up the coast to Nova Scotia before making the jump across? My friend stopped in St. Pierre (technically a French Overseas Territory) and said it was amazing (wine & cheese!) and it shortens the offshore voyage considerably. Food for thought!

  10. This boring Mississippi boater looks forward to reading of this great adventure! I will also be praying for your safety.

  11. Big fan of your photos and your writing!!
    Planning our own trip out of the Great Lakes and to saltier water.
    Will you take the st Lawrence out?

      1. That’s the path we’re taking, but definitely not that early. Sounds like an incredible journey, thanks for sharing it with us.
        Curious, will you ever bring her home, or are you both staying there

  12. My name is Michael and I have a home in Suttons Bay and my boat is in Northport (Hallberg Rassy 46 “Cygnus”) and I would very much like to sit and talk with you about your trip on the Mississippi and your upcoming trip to Europe. I will be at the boat yard this spring so perhaps we could meet there or have a cup of coffee in town?

  13. Jessie, you are beyond amazing! And Luke is beyond charming, gorgeous. I would give anything to have Jim and Louise meet him, see you so wildly happy together.

    Love you always, proud of you no matter what, AB

    Sent from my iPad


  14. I cant explain it, but your blog and your photographs are captivating. When I see katieandjesseonaboat show up in my inbox it makes my day. Thankyou!

  15. I am excited for you and your new journey. My husband and I have lived aboard our 30ft. sailboat, Tumbleweed, for the last two years. We are about to begin our Great Loop journey and then perhaps through the Panama Canal to the West Coast and beyond.

  16. You inspire me – been reading for some time now, new sailor at a young at heart 58 on the Detroit river/ lake St Clair imagine you coming along to expand our horizons – maybe this is a job in your future – safe travels best wishes – Debbie Fernandez

  17. So good to hear from you once again and getting caught up on your wonderful adventures. So looking forward to reading about the upcoming year. Best wishes for a wonderful, memorable and enriching FOREVER TIME.

  18. If you sail to Azores in April May you should not worry about Icebergs and Tropical Storms/hurricanes. Godspeed!

  19. If you are planning to run a video camera during this odessey you may want to give patron a serious think. By the time you finish your circle I would predict you can have a steady enough income to keep going. There are lots of armchair sales who would love to share your journey for a buck or five per month.

    All the best Nick b

  20. Good luck on your new adventures, both the crossing and your pending marriage. I had the pleasure of meeting you and speaking briefly with you and Katie last October in Annapolis. And have followed your blog and articles in Cruisers Outpost. I really like your style of writing, and wish Luke, yourself and Desiree all the best.

  21. I’ve used the Para-Tech back in 2000, and it kept our nose into the wind for 26 hours and saved our boat. Consistent +40 knots with gusting up to 70 at some times. Was quite scared the rope attaching the drogue to our boat would snap, so we used some chafing devices (some use a 1ft length of firehose, and then lash it over the drogue rope) to ease our concern.
    S/M-53: Vessel name Blue Cristal, Beneteau sloop, LOA 37′ 7” x 6. 5 Tons. Blue Cristal was tethered to a 15-ft. dia. Para-Tech sea anchor for 26 hours in Force 8-9 conditions on her way to Noumea from Bundaberg, Australia. Her owner reported satisfactory results – “The Para-Tech sea anchor worked very well… two other vessels in the area tried to sail out of it… one ended up 75 miles off course and the other ripped its mainsail and broke the forestay…”

    Better than dragging a couple used tires off the transom! Good luck out there you two, stay safe 😀

    1. Nice !!! Thanks for the recommendation, I’ll definitely look into it. The whole drogue controversy is an interesting one. But I am not planning on carrying spare tires so might not be a bad idea.

  22. CCA – Cruising Club of America; GRP – Glass Reinforced Plastic (surely you are being facetious when you say you don’t know what these mean?). Love your boat, have been a fan of Invictas for years (a guy called Tom Zydler used to write often in Cruising World about his and his wife’s travels in one, Mollymawk)

    1. CCA organises the Newport – Bermuda race, and the Invicta design was the first GRP boat to win it. I have heard of Mollymawk in fact I think we have a book it would be good to hear about their boat handling tips in large seas with a big stern overhang double handed.

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