HI, welcome back. For those I am welcoming for the first time, HI  – quick backstory for ya

I was 23 years old  (4 years ago… mmm) when my best friend Katie Smith and her pup Reggie, decided to buy a 27 foot sailboat and spend two years sailing America’s Great Loop. A lot of people asked how & why and at present I didn’t have much of an answer besides “why-not?”. The idea began as a joke. Neither of us had any qualification or prior knowledge on the subject-matter. It wasn’t until later that I found it’s meaning and I understood how the decision to travel this massive circle was the most educating adventure I could have ever signed myself up for. It completely re-routed the way I think, see, live, and move forward with every decision I make. In documenting this story over the years, I continue to receive emails of ambitious adventurers who aren’t quite certain where and how to start planning their own…  Over the next few weeks I will be answering a few of the most common questions asked. Beginning with –

” 5 Things to know before un-tying the lines “

1 – Draw out your plan

Literally. Get out a paper and a pen and start drawing. Most likely it is a map. Draw in your boat, your airstream, your motorbike, your vehicle of choice. Mark prospective waypoints. Jot down miles, dates, landmarks and goals. How does it look on paper? Do you look good on that map? I bet you look fantastic. Add to your drawing over time. Scribble all over it. Keep it vague. Grey areas are important. A plan is necessary yes, but make sure to factor in the ability to work around those plans when your plan – does not go to plan. When your artwork turns into reality it’s going to look a lot different than the masterpeice hanging on your fridge.  Allow yourself a daily visual of your adventure. You probably don’t know what the end reward is yet so wait to draw that in – that is, after all, the whole point of starting in the first place.

2 – Talk to people – real living people

Do your research. And by research I mean talk to people. Face to face, like we used to back in the day (Iphones’ Facetime not included). Pick as many brains as you can – people who have done something remotely similar. Retain that direct and firsthand knowledge before the information you may find on the internet machine. There is value in hearing as well as seeing one’s emotion behind their personal experience and words of wisdom.

We all know the word ‘naive’ is typically used in a negative context and is not how one would care to be categorized. But I am 100% certain there is a bit of magic that comes along with a teaspoon of naivety and I am here to tell you that it is okay to be naive – in small doses of course. One who is slightly naive does not share the same fears and resistance as the well-polished professor (I love you sister, this is not referring to you).  It’s okay not to know every detail, statistic, and hazard about what it is you are going to do. There is however, an art to being naive – the art is knowing exactly when you are being naive and to heighten your senses to everything that is happening around you. Without this art, your dose of naiveté is that of a tablespoon instead of a teaspoon and you might get yourself into trouble. That’s fine too, it will make for a better story.

When you talk to people about your plan, face to face that is, you will most likely find that they too didn’t have much of an idea of what they were getting themselves into. Carry on with your research. Learn what you can. The real learning won’t happen until you leave.

3- Pack light 

This is very straight forward and very important. The less you bring the less you have to lose. The less you leave behind the less you will miss. The less clutter the more space. The more stuff you have that can break, you more you will have to fix. We as humans require a fraction of goods we own to remain perfectly healthy and happy. Think simple. Pack light. (Katie was great at this, until it came to toiletries)

Invest in a “Spot” device. This satellite GPS tracker will send your location via email to your friends and family every day with the press of a button. Should you find yourself in an emergency situation it can also contact the Coast Guard. We pressed the “safe” button when we were securely anchored at the end of each day or after we successfully navigated an overnight passage or a long crossing. Only once did we have to use the “sort-of-an-emergency” button when we broke down on our way home from the Bahamas and had to get towed back to Florida.

Think seriously about what’s in your tool box. You are only as good as your tools and when something breaks – and I promise you it will – you are going to be the one to fix it. Investing in a good set of tools is priceless. We learned this the hard way time and again. We needed a very specific wrench to adjust part of the propeller shaft known as the “stuffing box” to prevent water from leaking into the boat. I could never bring myself to spend $30 on that stupid wrench, but every single time we were in a “slowly sinking” situation, I would have paid triple to have it.

Mmmm lets leave behind “Shades of Grey” and make room for guide books. Guide books often become your only source of information when you have no cell service and find yourself alone, possibly lost, and miles from civilization. Dozier’s “Waterway Guide” and “Skipper Bob” cruising guide series saved us a time or three. When you do have cell service and/or Wi-Fi available, I insist you download “Navionics.” You can pre-download incredibly accurate and detailed charts to your phone or tablet and still use them for navigation when out of touch.

4 – Leave your list incomplete

Don’t let an incomplete list keep you from leaving. Even when you think you have checked everything off there will be a never-ending psychological list patiently waiting. You will learn along the way what you need and more importantly what you don’t need. How does one gain experience without experiencing? You will make mistakes and If you already know you are going to make mistakes then listen, these are the 3 things to be certain to check off your list before departing :

1) Insure your boat – or whatever kind of vehicle it may be. When we left, I barely knew how to sail, nor motor Louise our 1979 Cal 27.  Having it insured freed me of the never ending anxiety I had every time I ran around (frequently)  hit a rock (twice in Canada) rammed a dock (when the shift cable snapped in the Bahamas) or backed into another boat, etc. (For the record I never backed into another boat).

2) Pre-flight. Every single morning before departing from point A, check the status of every working part in/on your boat to ensure it’s ability to get you to point B. When something goes wrong it goes wrong at a time of severe inconvenience, better to diagnose any potential problems while stationary.

3) Check your mental state. I am being completely serious. Your attitude and mental health is equally as important as the boat you are to rely on. Just like you rely on it, it relies on you. Don’t hesitate to wait a day, take a break, or call it quits early if you are not feeling up for it. Chill out mate. Tomorrow will be better.

The rest of the list will sort itself out. Carry on.

5 – You are superhuman 

So you have this idea…this grand plan…this wild adventure… it’s brewing thick as lava that molds to the mountainside while it cools. In your mind, acting on this possibility, is set in stone but in reality you are terrified to reach out and touch it because it might be unsafe. You spend your mornings justifying every reason under the sun to go for it and pass your afternoons shooing away the obnoxious list of reasons it’s not possible. This silent battle is your first and largest mistake. Put down your damn weapons and go. Make that first Progressive decision. You have the power over, and are in control of,  every decision small or large that you make. You will hold that power as long as you are alive. You are not stuck. Use this power to your advantage. This power is superhuman when you understand how to use it. You are superhuman. Turn that ridiculous drawing on your fridge into reality.

5 things before take-off-3 5 things before take-off-4 5 things before take-off-8 5 things before take-off-9


21 thoughts on “Turn that ridiculous drawing on your fridge into reality

  1. Sound advice for anyone considering cruising by boat. I enjoyed your blog adventures, and as Mark and Cindy have mentioned, miss reading them.
    Peter & Kathie
    s/v Citla
    (back in San Diego)

  2. Great article, Thanks for posting it, love the positivity exploding from it!!
    Miss you guys, and yes, Reggie too!

  3. Reefer pictures….I was all set to order a half dozen or so magnetic pictures for the fridge…!

    You are absolutely on the mark with your advise to the uninitiated. Prepare, plan, research then research some more then take another look at your plan and do final preparations. Only then is one ready to shove off into what has to be truly considered for what it is, A learning adventure for the soul.

  4. Sweet, I’m actually going to draw the map. And, this has reminded me I need to insure my effing boat. If I click the link in this article and get insurance from there do you get any proceeds?? ‘Cause I’d help a sista out!

  5. I read this awaiting the acceptance of an offer on my own “Louise”. If our paths ever cross, 1st round is on me.

  6. Hi Jessie,
    I liked your blog.

    Laura and I met a couple from England while we were traveling in the ICW. Their names are Martin and Bridget Green. Before they retired, they owned a commercial crab fishing operation , working the English Channel. They actually departed on their trip from Muskegon. They had purchased a partially completed Spray replica (Spray was Joshua Slocum’s boat that was the first to sail around the world single handed). They are currently in Green Cove Springs, Florida doing some maintenance. They plan is to sail the boat back to England in a year or so. Tentatively, they plan to return to Europe via Bermuda, then the Azores, then the Mediterranean Sea, then through the French canal system and back across the English Channel to home. What they don’t have right now is a crew, and crossing the Atlantic with only two people on board can be a grind.

    Anyway, I’m not sure what your future career plans are, but I thought I might give you a heads up if they contact you. They are nice folks. I only gave them the link to your blog.

    I also enjoyed your article in the spring Cruising Outpost. Good advice.
    Sent from my iPad


    1. Hey you! You should definitely have them contact me… this sounds like a really cool experience not to mention I would be pretty happy to be dumped off in England… Thanks for passing that along. Hope you and Laura are doing well !

  7. When I returned from extended cruising, I found the old adage-take half the clothing and twice the money-
    to be quite apt. Good to see another post from you Jess. Miss following along your adventures of the wayward sailor girls doing the loop with Reggie the wonder dog. Isn’t it bout time to get the next big extended life adventure trip started?

  8. Good to see you still writing, had a blast at the Miami boat show. Hopping my impatient waiting for a book will pay off. Are you still working on a book?

    Y’all are the best!

  9. Great great post and I just continue to be blown away by your photography. Are you self taught or any resources to offer up there? The light on the first and last photos at the end of the post in particular is EXQUISITE! So much talent. Are you on instagram? Would love to follow you there too.

  10. Hey Jessie,

    Great to see you blogging again. I well remember the two of us cramped in the aft locker tightening the nut on the stuffing box. Hope you and Katie are doing well. If you get back East, you always have a place to crash at our house/boat. We are getting ready to draw yet another map… retirement is very close.

  11. An awesome blog! Next, a book? What is the Atlantic Loop? What boat do you have?
    Pete M
    San Diego
    30′ Islander

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