“Cotter pin”

“Gem stone”




“Uncle Duff”

“Saran wrap”




This is a conversation. Katie was on the bow. I was in the cockpit. We had not seen each other in quite sometime so we didn’t waste time with small talk and preferred to catch up on what was important.  After a few rounds blurting the-first-word-that-pops-into-your-head, I remembered what it was like to be on a boat with Katie Ariel Smith. Hysterical.

It had been 23 months since she and I had been on a boat together but one would have assumed no time had passed. The majority of our time sailing “The Great Loop”  was not all rainbows and butterflies as I tried to convey that through my previous word vomit. Photography and writing can be a bit contradictory as my images may have provided a delightful insight of everyday beauty while my writing typically depicted some kind of disaster. But this most recent trip was different. I’ve just spent a week on the Wizard’s (dad’s) sailboat with Katie and her puppy “Duppy” (No, captain Reggie has not been replaced. Duppy the Super Puppy is just easier to travel with these days). I unfortunately don’t have a story for you what-so-ever, simply some photos worthy of sharing. It was freaking perfect. It actually was rainbows and butterflies. I was sweating chocolate, she was shitting glitter and Duppy was barking Adele. Literally nothing went wrong. (Except for that morning we pulled up the anchor and were drifting towards rocks and I went to steer us towards deeper water, come to find out I had forgotten to put the steering wheel back on after taking it off the night before). Aside from that I am still baffled at the ease of our delivery and can’t shake the thought that I was undeserving of such a sunshiny week. I kept waiting for something to blow up.

The plan was brilliant. Katie and I to sail Desireé to a tiny town called DeTour Village on the eastern tip of Michigan’s UP … where we would switch crew with the Wizard and his Wizardess girlfriend so they could explore Lake Huron’s North Channel, his favorite waters to sail. A good family friend and his kids were to delivery Desireé back to our homeport, giving us each one week to cruise around on this dreamy yawl.


D E S I R E É ::: 1 9 6 2  P e a r s o n  I n v i c t a  37′

The Invicta was the first fiberglass hull to win the Rhode Island to Bermuda race in 1964.  There are only 21 of these hulls ever built. My sister and I grew up as leisurely and obnoxious passengers on hull no. 8. Desireé was purchased by the Wizard in his early 20’s after his first attempt to sail America’s Great Loop on a Coronado 23 when he called it quits after reaching the Bahamas. Took him years to pay Desireé  off as a diesel mechanic before he and his best bud “Hawk” took off down the Mississippi in 1975 for his second attempt on Desireé , which was a success. The rest of his cruising years were spent exploring the Great Lakes with friends, family, my Mother, and eventually my Sister and me. Over 20,000 miles logged, this boat is a brick shithouse.

Now at 27 years old the Wizard trusted me of all humans to sail his first born child around the bi-polar Great Lakes. Mind-boggling, I know. I was fairly confident Katie and I would have no problem delivering Desireé from A to B. Felt similar to when she and I took off on Louise. We had never anchored, only docked a hand full of times and sailed the boat twice. My experience on Desireé paralleled my experience on Louise. This time we were just tacking on another 10 feet and 20 thousand pounds and hoping to sort it out along the way.

The differences in helming this yawl were endless but there were two particularly note worthy… the first one being… everything worked. Every button pressed did as it was told. Anything that spun, spun freely the right direction. Gauges operated in their proper zones. The plumbing worked. The stove worked. The water-pump worked. The auto-pilot worked. Battery life was abundant. The Engine turned over smooth as cracking a Budweiser. Gadgets and gizmos galore that we could actually rely on. That alone… was like a 5 star hotel.  For two gals mentally prepared for all possible malfunctions, we lived like queens for one week.

The second notable difference…was curious bystanders stopping in their tracks to admire. We didn’t know what these people were looking at cause surely it wasn’t Katie and me. We have aged. Gotten paler. Rounder. Lost our charm and ability to exude enthusiasm about most things in life unless it involves eating or sleeping. But Desireé has aged like fine wine. We were bombarded with questions about every inch of her. Questions we were not used to answering. This was odd. I accepted strangers adoration awkwardly as it was not my boat. I did not work for it. I did not varnish all of that (only a small corner). I did not put in that time, money, nor years worth of re-fitting. But it made me realize that I wanted to, and a high peak of appreciation had been met.  We were used to driving around a mast-less sailboat that casually spit out black smoke which looked like a yard-sale and typically bystanders were confused /somewhat concerned that we were even afloat. I was so focused on making sure I wasn’t going to bonk Desireé into anything that I genuinely blocked out the fact that I was helming an incredible sexy boat.

Okay that’s enough, you understand how I feel about this classic babe and I hope these images help you understand my language. Yes I am allowed to have a girl-crush, and no it is not on Katie. But gosh she makes me laugh and I will never have another friend like her.

Do me one more favor and scroll all the way to the end because I lied when I said I didn’t have a story for you.



So then the engine blew up. Serious. Believe it or not I was not on board.  The crew who were to bring her back to our homeport unfortunately got handed a crap sandwich. We received a call from them upon exiting the De Tour harbor on day one, that the engine crapped out. I am not going to bore you with all the technical details so long story short, there was a massive oil leak and it had run itself dry and you all know what that means. Criticize all you want. It happens.

At this very time, Jude Law (if you do not yet know about Jude Law I encourage you to explore your curiosity) was visiting me from England. My worst nightmare is his dream come true. My nightmare – the engine quitting, relying on sails only. His dream come true – no engine at all, relying on sails only. Well, his dream came true when two days after his arrival he learned that someone had to sail this boat home with no engine. I can’t say there is anyone else I would have willingly signed myself up to do so with a smile on my face? I knew it would be good for me. Good for us.

One hundred miles door to door we smashed out an overnight 20 hour delivery purely under sail from a winding channel in the Les Cheneaux Islands, past Mackinaw Island, under the bridge and through Gray’s Reef to the mooring ball in my back yard. I fed off of his confidence and learned to be at ease with the situation immediately. I could go on and on about the e p i c – n e s s  of those 20 hours. But there are only  three things you need to know for now:

  1. I think I actually sailed a sailboat.
  2. Desireé is home safely and needs an engine rebuild.
  3. Just before Luke (his name is Luke Yeates, not Jude Law) flew back to England… my celebrity crush got down on one knee.

Swear I am not making this up.

Desiree -1Desiree -2Desiree -3Desiree -5Desiree -4Desiree -6Desiree -7

33 thoughts on “G i r l c r u s h. It blew up. Down on one knee.

  1. Aaaaaaaaaaa! That sent chills down my spine! Congratulations!!!!!! What a great story- made my day!!! Wishing you two a lifetime of adventures and happiness together!

  2. as always a joy to hear from you, what a great writer, tom the trailer sailer.

    On Wed, Sep 7, 2016 at 8:43 AM, KATIE & JESSIE ON A BOAT wrote:

    > katieandjessieonaboat posted: “”Scorpion” “Cotter pin” “Gem stone” > “Earwax” “Pancakes” “Wood” “Uncle Duff” “Saran wrap” “Korea” “Beyonce” > “Staple” This is a conversation. Katie was on the bow. I was in the > cockpit. We had not seen each other in quite sometime so we didn’t waste > time w” >

  3. Cool beans. Thx.

    On Sep 7, 2016 8:44 AM, “KATIE & JESSIE ON A BOAT” wrote:

    > katieandjessieonaboat posted: “”Scorpion” “Cotter pin” “Gem stone” > “Earwax” “Pancakes” “Wood” “Uncle Duff” “Saran wrap” “Korea” “Beyonce” > “Staple” This is a conversation. Katie was on the bow. I was in the > cockpit. We had not seen each other in quite sometime so we didn’t waste > time w” >

  4. Great story and great pictures.
    Publish it in a mag like Traverse. What an adventure. Plus Sweet Jesse James said yes! Just got a news flash someone robbed a bank in Leelanau County. It wasn’t you Jesse? LOL

  5. Wonderful adventure, story and pictures as always! Love to see the fun times through your eyes! I am so happy for you & Katie! Great friends are life’s treasures! My favorite part of the story? Down on one knee! Love it! Life is so good! Congratulations!

    PS: Just picked up the new Cruising Outpost and I am excited to read yet, another article! You go girl!

  6. Nice post. I always look forward to your stories. Interesting coincidences. We started sailing and still own a 1979 Pearson 40. We also have a Hunter 460 that we are now living on. The Pearson is named Cool Hand. We liked the name so we changed the name of the Hunter from Desiree to Cool Hand Too.

  7. Dear Jess, this is truly your best ever post! Beautiful photos, and wonderful script! Have read it 3 times over, better each time. Xoxoxo, AB

  8. Jesse,
    What did you say?
    Did you want an answer right now?
    Do you need a ride to the airport?

    I’m glad I read the whole post,

    Did I say CONGRATS?


  9. Gotta say, as I read #3, I was half expecting you to finish that sentence with “… and fixed the engine.” But congrats, nevertheless!

    Are you and/or Katie going to be in the SF Bay area at all in 2017? I’ve been suckered into… I mean, “promoted to” Rear Commodore of the Berkeley Yacht Club, and I’m looking for guest speakers for our dinner meetings next year. Missed your talk at the Richmond boat show last April. Love to hear it some day.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s