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Jon Totten joins Cruisers Academy in Mexico!

Whether it’s teaching sailing in the Caribbean, trekking across the country with a J105 in tow, racing a trimaran in the 'Race to Alaska' from Washington, or starting his non-profit sailing program in Idaho—Jon Totten does it all. What’s true to him, like with many long-time sailors and instructors, is how his best and worst days of sailing have taught him how to be a better human being.


Jon’s discovery of sailing doesn’t sound all that unfamiliar; it happened accidentally. While getting his Resource Recreation and Tourism degree from the University of Idaho, he stumbled upon the North Idaho College Outdoor Pursuits Program, and the head of the sailing program pursued him as a replacement for the current coach at the time.


Their exchange went something like this:

“Do you know how to sail?”, asked the program leader.
“No,” said Jon.
“Do you wanna learn?”
“You bet.”

From there, Jon was sent to a two day basic sailing course in the Puget Sound. By the following week, "I was teaching sailing to college kids, making it up pretty much.”


Growing up on a farm in Wisconsin, Jon was used to doing things daily that required rolling with the punches and taking on new challenges. It allowed him to learn that much faster. His dad would get the tractor in gear, throw Jon on and tell him to plow the field with no knowledge of how to actually stop the heavy equipment. This "fly by the seat of your pants" style of learning was summed up in a line his dad used to feed him: “The first rule of tree climbing is don’t let go…there is no rule number two.”

Jon in the Grenada Sailing Week edition of Caribbean Compass
Grenada Sailing Week in March 2019 with Jon and crew

From the start, Jon brought that mindset to teaching sailing and in his racing journey. After Jon recieved his Masters in Education and taught for 12 years in Higher Ed, he parlied his experience as a leader into becoming an American Sailing School instructor. When he first started, however, "I’d anchored a boat once in my life….,” Jon recalls. But that was just the beginning.


As he racked up years of teaching with ASA and competitive racing, the young man who had stumbled upon teaching sailing as a fun after school activity, became a seasoned sailing professional.


Over many nautical miles sailed in the San Juan Islands, years of back-to-back trips in the Southern Caribbean, and ocean crossings, Jon recognized that one of the most influential aspects of being a Captain was his own state of mind. “Literally people hear the splash of you jumping in and they get out of bed… because it motivates them,” Jon explains. Being an instructor requires having an awareness of how your moods and actions define the experience for everyone else, particularly when anchoring in a new spot or making an unfamiliar journey overnight.


Jon sitting at the helm of sailboat, wearing a Cruiser's Academy long-sleeve
Jon, in his teaching element

There are moments when “It’s blowing 44 knots…it’s f****** loud and we got to go reef the sail…,” Jon states, matter-of-factly. To him, the best thing he can do as a captain and a teacher is to keep a level head and take action, enabling his students to do the same.


Beyond the adrenaline that is often involved in acting under pressure, when left to fail in certain circumstances, Jon sees how people can experience breakthroughs in learning, something he has experienced himself and with the hundreds of students he's taught.

“Man, I’ll tell you a story about when I ran aground, or when I tore a sail in half or when I crashed a boat into a dock….,” Jon admits. His gratitude for these experiences in his journey of becoming the Captain he is today, is a mindset he passes on to his students.


Putting his students at the helm and guiding them through the actions where they are the ones sailing, facing the discomfort, and experiencing something they haven't before is how Jon creates that unique teaching experience and connection to his students. What's more is that these lessons apply far beyond sailing; they teach us how to respond to challenges and push us to become better versions of ourselves. Sailing is one of the most beautiful and challenging conduits for learning about nature, ourselves, and life.


Jon's firsthand experience of how sailing has enabled him to become the best version of himself, it was inspired him to start his own therapeutic sailing non-profit, DogSmile Adventures.


The DogSmile mission statement is simple: sailing makes you feel better, Jon explains ,“The lake and the boat do the work, I just put people there.”

DogSmile’s focus is on providing these experiences for youth, veterans, people with developmental or physical disabilities and those overcoming abuse in any form. But really it’s open to anyone who believes that they can benefit from sailing. Now, he has spent more than three years running his program where just this season alone he has led more than one group a day for 25 day increments, non-stop. In that time, he has taught people with all different personal stories and experiences that get to participate in this unique, healing experience.


The benefits and impact of being out on the water unfold organically, both for the crew and himself. Jon recounts a story from one particularly special evening where this felt especially true: "...I can tell everyone is looking at me and really expecting me to say something…and I just didn’t…. I very consciously did not speak and I watched everyone just settle into the moment.” By creating these moments for his students, they unlock the connection to the water, the boat, and themselves.


Brady explains how this collaboration with Jon has been a long time coming, "When we first met Jon in the Caribbean, there was an instant connection. Our friendship has only grown through sailing together and starting our own businesses alongside each other. It was only a matter of time until we we would collaborate with Jon and we are stoked that time has finally come."

Brady continues, "We take it incredibly seriously who we choose to teach under the Cruisers Academy name, and Jon not only meets that bar, but exceeds it by miles."

This coming April and May Jon will be leading Cruisers Academy sailing trips in Mexico. On board, Jon will bring his decades of teaching and sailing experience, his learn-by-doing approach, and can-do attitude that has made him an incredible sailor, Captain, instructor and human being. More than that, Jon will bring his unique ability and love for making new friends and facilitating the connection with oneself that sailing provides. He explains one if his favorite things to do with students aboard,


“I love giving them that space to just sit and tell me…why do you want to do this?”

Jon will be captaining three trips in and out of La Paz, the famous Baja Sur city on the Sea of Cortez. The first 9-day trip, running from April 3-11, 2024, will be a multiday/night passage from Mazatlan to La Paz. The second week-long trip will take place from April 23-29, 2024, and include island hopping to the world-famous islands of Isla Espiritu, Isla Partida, and Playa Balandra. Last but not least, John will be captioning a third longer course from La Paz to San Carlos from May 2-11, 2024. This trip will include exploring La Paz, and the dreamy Isla Espiritu, and an overnight passage from La Paz to San Carlos on mainland Mexico.


We'll be opening bunks for each leg, and accepting only 2-3 students for each passage to keep the Mexico sailing course personal. This will be a dynamic learning environment, with the opportunity to put to work any sailing experience you may already have with lots of room to include new lessons and first-hand experience of living the sailor lifestyle.



Topics covered in these sailing courses will include…

  • Weather forecasting

  • Passage planning

  • Essential offshore safety

  • Boat systems management

  • How to keep watch at night and during the day

  • 'Best Practices' aboard

  • International sailing logistics

  • Anchoring

  • Provisioning & cooking underway

  • Crew dynamics and responsibilities

  • Highs and lows of living aboard

  • Lots of time at the helm and working the lines

Jon having fun at the helm
Jon pointing to the incredible views that you'll be seeing on the Mexico Cruising trips!

This blog was brought to you by Kira Kessel, a young Cruiser who sailed the South Pacific with her family and is enraptured by the cruising lifestyle!

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