Embark on an Unforgettable Journey: Your Guide to Learning Sailing in the Exumas, Bahamas

The initial wave of seasickness crept in subtly, not with the dramatic force of a rogue wave described in sailing lore, but more like an insidious, rising tide. Yet, the telltale signs were undeniable: clammy skin, a racing pulse, and the unmistakable onset of nausea.

The timing couldn’t have been worse. I had just landed in the Bahamas the previous night, poised to embark on a week-long, immersive learn-to-sail adventure in the secluded Exuma out-islands. However, it wasn’t the ocean’s motion triggering my queasiness.

Discover extraordinary destinations accessible only by water when learning to sail with Nautilus Sailing.

The immediate concern was the opulent yacht docked ahead, its $1.4 million bow looming perilously close to our own vessel. I had volunteered to “fend off” as we navigated out of Palm Cay Marina. Now, it seemed I was more likely to sink us all before we even cleared the slip.

“Five feet!” I called out from the foredeck, counting down the shrinking gap. “Three feet! Two feet . . . !”. Bracing myself, I anticipated the sickening crunch of colliding fiberglass.

Then, miraculously, as if guided by an invisible hand, our 40-foot Lagoon catamaran, Never Say Never, shuddered to a halt, reversed with surprising agility, and gracefully swung to starboard, narrowly avoiding contact by mere inches, before setting course for open waters.

Turning back towards the stern, I saw our seasoned boat captain and instructor, Tim Jenne, flash a reassuring, wide-smiled thumbs up from the helm. I had just absorbed the cardinal rule of sailboat operation: “Don’t hit anything.” This initial heart-stopping moment was just the beginning of my deep dive into Learning Sailing.

Discovering the Writer’s Life – Under Sail: An Immersive Approach to Learning Sailing

Experience the writer’s life under sail, a unique journey of discovery and skill acquisition in sailing.

The allure of spending years “cruising” on a sailboat, escaping the conventional rhythm of life, had always captivated me.

In my mid-twenties, this dream felt tantalizingly within reach. If the essence of being a writer was to experience the world and translate those experiences into words, what better source of inspiration than island-hopping across the equator, immersing oneself in diverse cultures? Living on a boat also unveiled a surprisingly practical aspect – beyond the costs of food, fuel, rum, and occasional repairs, it was essentially a floating, rent-free existence.

Following college, I relocated to Key West, Florida, and invested in a weathered 30-foot sailboat named No Paine. For the subsequent three years, I lived aboard, meticulously restoring her while absorbing the intricacies of each onboard system and adapting to life on the water, all in preparation for a safe ocean crossing. I also developed an insatiable appetite for nautical literature, devouring books with titles like Fatal Forecast and Where There Is No Doctor, filling my mind with technical knowledge that felt as weighty as physical ballast.

The envisioned circumnavigation from my twenties never materialized. I did, however, gain valuable experience crewing a 44-foot yacht across the formidable Southern Ocean from New Zealand to Argentina in my thirties. But upon arriving in Nassau, it had been decades since I had actively engaged in any serious sailing. This Exumas adventure was a re-entry point, a chance to reignite my passion for learning sailing and the open sea.

Our week-long, live aboard sailing course commenced under gentle breezes, providing an ideal environment to … [+] familiarize ourselves with our vessel, a 40′ catamaran christened Never Say Never.

Gentle winds provide the perfect conditions to begin learning sailing and familiarize yourself with a 40-foot catamaran.

The author, preparing to reignite his learning sailing journey in the stunning Exumas of the Bahamas.

The author’s return to sailing: preparing for a learning experience in the beautiful Exumas.

My girlfriend, Eliza, in contrast, had never been drawn to the allure of long-distance cruising. Despite her background as a SCUBA instructor, she had always been content with leisurely sails closer to shore, accompanied by wine and cheese. Until recently, that is.

With one son now in college and another soon to follow, the prospect of a luxurious, floating fiberglass suite that could traverse the globe began to sound considerably more appealing than an empty nest. Consequently, last year we decided to take the first step towards realizing this vision: learning sailing together through a professional, accredited live aboard course. This quest led us to Nautilus Sailing.

The third member of our learning sailing cohort was Diana, a former Mormon-turned-sailboat racer from Texas. Diana had diligently built her sailing resume over recent years, driven by the ambition of undertaking a solo ocean crossing one day.

Eliza and our captain and instructor, Tim Jenne, prepare for the start of Day 1 of our week-long … [+] live aboard sailing course, eager to begin the practical aspects of learning sailing.

Ready to learn sailing: Eliza and Captain Tim Jenne embark on their week-long liveaboard course.

Nautilus Sailing was established in 2010 by Tim Geisler, a California surfer who transitioned to Colorado. Sailing initially served as Geisler’s method for discovering secluded South Pacific reef breaks.

His entrepreneurial journey is a classic tale of turning adversity into opportunity. The Great Recession of 2008 led to Geisler losing his position as VP of a global non-profit, ultimately resulting in foreclosure on investment properties when tenants defaulted on rent. They also lost their dream home under construction near Crested Butte.

“The silver lining,” Geisler recalls, “was that the recession forced us to pause and reinvent ourselves. We decided to merge our passions for sailing, education, and adventure into a new venture. Nautilus started modestly, but we steadily attracted new clients and destinations. Our primary challenge soon became managing cash flow. There were times when I had to sleep in my car at the airport because I couldn’t afford a hotel room.”

Nautilus Founder, Tim Geisler, transformed his passion for sailing, education, and adventure into a thriving business … [+] during the Great Recession. Today, it’s a leading ASA-accredited sailing school with global destinations.

Tim Geisler, Nautilus Founder, built a successful sailing school by merging his passions for education and adventure.

As Nautilus expanded, Geisler’s next hurdle was finding enough qualified instructors who not only possessed deep sailing expertise but also the right disposition for teaching. This is crucial in learning sailing effectively.

“My instructors in California were mostly grizzled old salts who struggled to connect with students,” Geisler remembers of his own early experiences learning sailing. “Yelling seemed to be their primary teaching method. It became clear that Nautilus’s unique opportunity lay in creating a sailing school with instructors equally passionate about teaching and the ocean. Back then, no one was really focusing on the demographic of 30 to 55-year-old professionals in their peak earning years. I realized that by combining high-quality boats with learning to cruise in stunning locations like the Bahamas, Tahiti, and Mexico, we could build a truly successful business.”

Fourteen years later, Nautilus stands as one of the most respected and prolific American Sailing Association (ASA) certified schools in North America. They offer numerous live aboard courses annually, ranging from introductory programs like Sailing Made Easy 101 to advanced “bluewater” ocean passage training, catering to all levels of learning sailing.

Our Nautilus instructor, Tim Jenne, blends extensive sailing experience with a contagious enthusiasm for the … [+] ocean and a natural gift for teaching and connecting with students, enhancing the learning sailing experience.

Tim Jenne, Nautilus Instructor, combines sailing expertise with a passion for teaching, enriching the learning experience.

Eliza diligently studies above deck for our first ASA 101 Sailing Made Easy exam, achieving an impressive score of 98%, demonstrating her dedication to learning sailing theory.

Theoretical learning in sailing: Eliza prepares for her ASA 101 exam, scoring an impressive 98%.

After our near-miss departing Palm Cay, Jenne steered Never Say Never out of the channel, heading 155 degrees south-southeast. Our course for the next five hours would take us 35 miles across the shallow Exuma Bank towards Norman’s Cay, a long, narrow island once infamous as the Medellin cartel’s primary cocaine smuggling hub between Colombia and America.

The day’s forecast predicted light to nonexistent winds. Consequently, instead of raising sail upon reaching open water, Jenne utilized the opportunity to familiarize Diana, Eliza, and me with our boat’s anatomy and its “feel” underway through a series of engine, steering, and maneuvering drills. These exercises are foundational in learning sailing, even before harnessing the wind.

We each took turns sharply turning the wheel hard to port and starboard, experiencing Never Say Never’s “turning radius”. Next, we engaged the twin diesel engines, alternating between full forward and full reverse, developing a sense of acceleration and stopping distances. Finally, we practiced man-overboard recovery drills with an inflatable buoy named “Pepe,” who had a recurring habit of playfully falling overboard. Throughout these drills, Jenne keenly observed our communication and teamwork, offering timely advice and encouragement, crucial elements in learning sailing as a team.

“Skill repetition and scenario drills are vital components of this week,” he explained as we hoisted Pepe back aboard one last time. “If you’re at the helm, do you know precisely how to react if someone falls overboard? What if it occurs at night? How quickly can you turn or stop to avoid a collision? In unexpected situations, knowing your boat’s capabilities can be the decisive factor.” This emphasis on practical skills is central to the liveaboard learning sailing approach.

That evening, we anchored in the sheltered lee of Norman’s Cay, as the deep mango sunset melted into the tranquil, blue ice of the water. Behind us, over the dunes, a nearly full moon ascended in perfect symmetry on the opposite horizon. The only other presence on the horizon was the silhouette of a superyacht anchored a few miles distant.

“This is my favorite time of day,” Jenne remarked, settling into a beanbag chair on the aft deck. “Too bad you three have to study.” He added with a wink, highlighting the balance between practical experience and theoretical learning sailing.

Eliza savors the tranquility of learning sailing after anchoring at sunset in the lee of Norman’s … [+] Cay, reflecting on the day’s lessons and preparing for more.

Evening tranquility after learning sailing: Eliza relaxes at anchor, reflecting on the day’s lessons.

Jenne’s meticulous attention to detail and teaching prowess are matched by his passion for … [+] the ocean and sailing, honed by five years of service in the U.S. Coast Guard, bringing invaluable real-world experience to the learning sailing environment.

Tim Jenne’s expertise: honed by Coast Guard service, enriching the learning sailing experience for students.

Jenne embodies the kind of individual writers are drawn to portray. His personality is perfectly suited for learning sailing instruction.

Initially, he appears somewhat reserved and understated. Yet, I soon discovered a gregarious and humorous side, underpinned by a vast reservoir of life experiences. Physically agile and mentally sharp, his mind constantly anticipates the next maneuver. His passion for the ocean is infectious, making him an ideal mentor in learning sailing.

Jenne’s first encounter with sailing was at age 13 in Washington State, aboard a small boat launched from a local beach with a neighbor. He vividly recalls the magical sensation as the boat caught the wind and began to float. “Then, as we lowered the centerboard and leaned back,” he recounts, “we were flying. It was the most exhilarating experience of my life.” This early thrill sparked a lifelong journey of learning sailing.

Sailing quickly became Jenne’s all-consuming passion. Outside of school, he dedicated his free time to studying boats and constructing experimental models from Styrofoam and bed sheets. At 16, driven by a desire to serve, he joined the U.S. Coast Guard in 1984, specializing in search and rescue (SAR) in the treacherous waters of the Pacific Northwest. This background provides a unique perspective to his approach to learning sailing.

“SAR missions typically occur in adverse weather,” Jenne recalls of his five years of active duty. “I encountered some genuinely perilous situations: 60-knot hurricane-force winds, 45-foot waves, sailors requiring IVs due to severe dehydration. These experiences instilled in me the ability to remain calm under pressure and taught me to avoid overreacting in critical moments.” These are invaluable lessons he imparts to his students learning sailing.

One of the crucial aspects of learning to sail is stepping outside your comfort zone, embracing challenges, and … [+] accepting the inherent uncertainties of the sea, all part of the transformative learning sailing process.

Embracing challenges: a key component of learning sailing and personal development.

“Slow is smooth, smooth is fast.” Jenne’s calm and effective teaching method has been refined over … [+] hundreds of Nautilus courses, optimizing the learning sailing experience for countless students.

Effective teaching in sailing: Jenne’s calm approach, honed over many courses, enhances learning.

These demanding experiences shaped Jenne’s gentle yet effective “slow is smooth, smooth is fast” teaching philosophy, a quality Geisler had sought in instructors for years. This patient approach is particularly beneficial for those new to learning sailing.

During skill practice, Jenne never barks orders. When we feel overwhelmed, he encourages us to verbalize our thought processes in real-time. And at the close of each day, we dedicate time to discuss what worked, what didn’t, and why – facilitating continuous improvement. This reflective practice is vital in learning sailing.

Crucially, Jenne exudes a steadying presence that naturally puts people at ease. Wind and water are powerful forces, and so are boats. When things go awry, the consequences can be significant. Consequently, Jenne emphasizes that a major part of learning sailing is conquering fear.

“Sailing and the ocean will always hold unknowns,” he explains. “But to experience the magic of anything new in life, you must first overcome the fear of initiation. Learning sailing is no different. It’s about challenging yourself, and a significant part of that is allowing yourself to venture beyond your comfort zone.”

The Bahamas “Sun Salutation”: One of the most rewarding aspects of learning to sail is beginning each … [+] day on the water, immersed in the beauty of nature.

Bahamas “Sun Salutation”: Daily immersion in nature is a reward of learning to sail.

Day 2 of our course dawned cloudless, with a gentle easterly wind rippling the water just past high tide. Jenne was already on deck at sunrise, checking lines, preparing sails, and monitoring the weather on his iPad. Diana, Eliza, and I were engrossed below, cramming for our next exam. The theoretical component is a crucial part of learning sailing.

At 8:00 am, Jenne placed our first ASA sailing test on the cockpit table with a decisive thud. The accompanying #2 pencils and exam atmosphere evoked a momentary flashback to school-day anxieties.

I was acutely aware of the stakes: if we all passed this test and three subsequent ones throughout the week, Diana, Eliza, and I would officially be certified to charter a sailboat virtually anywhere globally. The sheer audacity of the proposition was almost comical: who in their right mind would entrust me with the keys to a multi-million-dollar sailboat right now and say, “See you in a week”? Yet, the ASA certification is a recognized standard in learning sailing and competence.

However, as I opened the test and began filling in the answer bubbles, I quickly realized I possessed far more knowledge than I had initially believed. The immersive environment of learning sailing was clearly effective.

If you grow up by the water, there’s a good chance that sailing is in your DNA. Our anchorage at … [+] Warderick Cay, located in the heart of the Exumas Land and Sea Park, offers a stunning backdrop for learning sailing.

Warderick Cay anchorage: a picturesque location for learning sailing amidst natural beauty.

The author takes the helm of Never Say Never, fully embracing his role as Captain of the Day and … [+] applying the skills learned through the sailing course.

Captain for a day: the author helming Never Say Never, demonstrating his learning sailing progress.

People pursue learning sailing for diverse reasons.

For those raised near the ocean, it might be an inherent part of their heritage. For many others, boats are simply tools for recreational activities like fishing or scuba diving. More traditional enthusiasts may be drawn to the yacht club culture and aesthetic.

Then, there are individuals like Jenne, Diana, Eliza, and myself, who are driven to sail to push their personal boundaries and embark on a journey of self-discovery. This deeper motivation resonates strongly with those learning sailing.

Unsurprisingly, Nautilus students often share these traits: they are typically high-achievers who enjoy challenges and introspection. Professionally, they are frequently CEOs, entrepreneurs, and startup founders seeking to enhance their leadership skills and build stronger teams. The parallels between leadership and seamanship are often explored in learning sailing environments.

“Our course participants are typically very successful in their respective fields,” Jenne explained. “They enjoy challenging pursuits, and their strong desire for freedom is a significant motivator, often why they are entrepreneurs in the first place – they thrive on autonomy and self-determination. When crossing an ocean, self-reliance is paramount. The risks and lessons in sailing and entrepreneurship are remarkably similar.” This connection between personal and professional growth is a valuable aspect of learning sailing.

Plotting routes, programming Never Say Never’s instruments, and mastering the names of lines and rigging … [+] are essential practical skills taught during the week-long sailing course, fundamental to learning sailing effectively.

Essential sailing skills: route plotting and instrument programming are key to learning sailing.

After acing our ASA 101 test (everyone scored 95% or higher), Diana, Eliza, and I raised anchor and steered Never Say Never almost directly south. Our theoretical knowledge was now being reinforced by practical application in learning sailing.

We were still under the influence of a high-pressure system that had lingered over the Bahamas for a week. So, rather than attempting to sail in the continued light winds, we opted to motor along the inner edge of Exuma Bank for another day. After a lunch stop at Shroud Cay, we would continue south to Warderick Cay, our base within the Exuma Cays Land and Sea Park for the remainder of our trip.

En route, Jenne imparted more practical skills essential for our week, supplementing the theory and rules of navigation. These included programming Never Say Never’s instruments and managing the colorful array of lines in the cockpit that control the sails. This hands-on experience is at the heart of learning sailing effectively.

Nautilus live aboard sailing courses emphasize both theoretical knowledge and practical skill … [+] development, even as the sun sets, highlighting the immersive nature of learning sailing.

Immersive learning sailing: Nautilus courses balance theory and practice, extending through sunset.

By the end of a Nautilus live aboard course, students become proficient in a wide range of skills, from … [+] basic knot tying to understanding complex maritime rules and regulations, showcasing the comprehensive nature of learning sailing with Nautilus.

Comprehensive sailing education: Nautilus courses ensure proficiency in diverse sailing skills and knowledge.

One of the enduring paradoxes of sailboats is that despite the extensive knowledge and skill required to operate them safely, financial resources are often the only barrier to ownership. This contrasts sharply with aviation or commercial trucking, which mandate rigorous training and licensing. This reality underscores the importance of voluntary education in learning sailing and maritime safety.

As a result, Nautilus’s live aboard sailing courses heavily emphasize both theoretical study and practical skill-building, beginning with basic knot tying and progressing to deciphering the complex language of buoys and lights guiding sailors. Jenne also excels at teaching the more intuitive aspects of sailing, like reading wind and water patterns and using cloud formations for weather forecasting. These are the nuanced skills that elevate learning sailing from a technical exercise to an art form.

“Early mariners relied solely on time on the water to understand their environment,” Jenne explained, gesturing towards the array of touchscreens at Never Say Never’s helm. “Today, we have real-time satellite data to inform split-second decisions. But experience, instinct, and feel remain irreplaceable.” This blend of technology and traditional seamanship is crucial in modern learning sailing.

Our anchorage at Warderick Cay is a tropical haven, largely untouched by human presence, save for a few … [+] other sailboats, offering a sense of secluded paradise for those learning sailing.

Tropical paradise for sailors: Warderick Cay anchorage offers seclusion and natural beauty for learners.

The summit of Boot Hill, adorned with hundreds of driftwood plaques left by passing cruisers, stands as a … [+] testament to the sailing community and shared journeys, inspiring those learning sailing to envision their own voyages.

Boot Hill memorial: driftwood plaques left by cruisers, symbolizing the shared journeys of the sailing community.

Later that afternoon, we sailed into Warderick Cay amidst a small flotilla of charter boats moored along the anchorage’s main channel. After securing our sails, we hiked to Boo Boo Hill, the island’s highest point. This scrubby, sun-bleached summit was decorated with hundreds of driftwood plaques commemorating the names of cruising boats that had visited before. This tradition connects current learners to the rich history of learning sailing and exploration.

It was a weathered tribute to humanity in a largely uninhabited locale. Yet, on the descent, what resonated most powerfully was that the privilege of being here had little to do with wealth. Every boat present had undertaken similar risks to reach this remote haven. This shared experience and camaraderie, Jenne explained, is unique among sailors. This sense of community is often a surprising and rewarding aspect of learning sailing.

“We look out for each other out here,” he said. “Knowing someone is a sailor and has experienced places and moments like this, you instantly understand a lot about their character, regardless of their boat’s size. Mariners are special in this way. We’re more like a tribe.” This tribal aspect of sailing culture is often embraced by those learning sailing.

Eliza skillfully navigates Never Say Never through the narrow cut south of Warderick Cay into … [+] open water, guided by Jenne to maintain a safe distance from the reefs, showcasing her growing confidence in sailing skills.

Navigating narrow channels: Eliza’s growing sailing skills are evident as she helms Never Say Never.

The following morning, Diana, Eliza, and I emerged from our cabins to the high-pitched whistle of wind in Never Say Never’s rigging – an unmistakable sign of increasing wind. Jenne was already on deck, observing an anchorage dotted with whitecaps. The rising wind presented an exciting opportunity to apply our learning sailing skills in more challenging conditions.

Our destination for the day, roughly forty miles south, was Staniel Cay and Thunderball Grotto, the location for underwater cave scenes in the James Bond film of the same name. Staniel Cay also boasted a marina with a quirky, Jimmy Buffett-esque bar and restaurant, marking our first and only planned night ashore. This provided a social and relaxed break from the intensive learning sailing schedule.

With a brisk breeze now consistently blowing, we decided to sail on the outer edge of Exuma Bank. This meant finally sailing with full canvas and venturing into open water, where the seabed drops away, allowing waves to build without obstruction. This transition to open water sailing is a significant step in learning sailing.

Never Say Never finally gets underway under sail, harnessing the wind power that is central to the art of sailing.

Under sail at last: Never Say Never harnesses the wind, a thrilling aspect of learning sailing.

“Remember, this is what you came here for,” Jenne shouted over the wind as Diana and I raised the mainsail and Eliza steered the boat through the narrow channel, expertly navigating waves breaking close on either side. “Prepare for lift off!” This exhilarating moment was a culmination of our learning sailing journey.

Moments later, clear of the channel and into bluewater, Never Say Never caught a strong gust, heeled to starboard, and surged forward, propelled by the invisible forces of physics. In that moment, the thrill was palpable, a profound reward of learning sailing.

I glanced back at Eliza, ensuring she was sharing the experience. She was already beaming, arms outstretched, each hand framing opposite ends of a rainbow arcing across the horizon.

“Is this it?” she asked Jenne, grinning. “Is this that magic you were talking about?” This magical moment perfectly encapsulated the allure of learning sailing.

Eliza captures the “magic” rainbow, a symbol of the enchanting experiences encountered while learning to sail in the Bahamas.

Rainbow magic: Eliza captures a rainbow, a symbol of the enchanting journey of learning sailing.

The Staniel Cay Yacht Club bar and restaurant, a Jimmy Buffett-esque cruiser’s paradise, offers a … [+] relaxed and social atmosphere for sailors from around the world, a perfect respite after a day of learning sailing.

Staniel Cay Yacht Club: a social hub for sailors, offering relaxation after learning sailing.

That evening at Staniel Cay Yacht Club, the bar was buzzing with sailors from across the globe, the energy rising with each passing minute. Some, like us, were clearly charter guests on a schedule. Others, more weathered and relaxed, appeared to have been there for months. This diverse community is part of the charm of the sailing world, and interacting with them enhances the learning sailing experience.

In moments like these, nostalgia for my Key West days resurfaced, a longing for that simpler sailing life. This was the sailing “world” I had dreamed of writing about in my twenties. Perhaps it still could be. Regardless, thanks to Jenne and Nautilus, I now possessed a far clearer understanding of what I was doing compared to two decades prior. This newfound confidence is a direct result of learning sailing through a structured course.

“That’s the beauty of sailing,” Jenne reflected as we rowed back to the boat. “It’s never too late. Never say never . . .” This sentiment perfectly encapsulates the enduring appeal of learning sailing at any stage of life.

A perfect downwind run to Nassau: “Remember that this is what you came here for,” Jenne reminds us as we … [+] apply our newly acquired sailing skills on our return journey, solidifying the learning sailing experience.

Downwind sailing: applying newly learned skills on the return to Nassau, reinforcing the learning process.

On our final morning before returning to Nassau, Diana, Eliza, and I tackled our last ASA exam under clearing skies. During the downwind sail north, Jenne attached a lure to a fishing rod, let out the line, and observed rather than instructed. He entrusted us to sail Never Say Never home, a testament to our progress in learning sailing.

Team building isn’t explicitly part of the Nautilus curriculum. Yet, it’s an integral lesson Jenne aims to impart. In naval settings, clearly defined roles are essential for order and mission success. For most, the nuances of teamwork often require learning and relearning. In this sense, becoming a proficient sailor is akin to training a puppy: clear intent, precise direction, and repetition are key. Sailing, with its inherent challenges and rewards, is an exceptional vehicle for reinforcing these lessons and fostering teamwork, a valuable soft skill gained through learning sailing.

“Ultimately, being a boat captain isn’t about issuing commands,” Jenne explained. “It’s about perspective, understanding, and knowing when to step back. It’s also about being willing to perform any task, recognizing that no job is beneath you. The same principles apply to life. If you embrace this philosophy, you’ll cultivate lasting friendships and relationships.” These life lessons are an unexpected yet profound benefit of learning sailing.

Officially ASA certified! Diana and Eliza celebrate their achievement on the final day of the Nautilus … [+] live aboard course, marking the culmination of their learning sailing journey.

ASA certified sailors: Diana and Eliza celebrate their accomplishment, a milestone in their sailing journey.

Exumas, Bahamas: Easy to reach, incredibly hard to leave, a testament to the allure of sailing and the beauty of the destination.

Exumas allure: beautiful and unforgettable, a perfect setting for learning sailing and adventure.

Later that evening, after docking Never Say Never back in our Palm Cay slip, I felt a sense of philosophical reflection as our trip concluded. For centuries, sailors have sought wisdom from the sea. What insights had I gained in the past week through learning sailing?

It’s a question Jenne often poses to his students on the final night, as the answers reflect his teaching effectiveness. For me, the conclusions were clear:

First, accept what you cannot control. Many aspects, especially involving the ocean, are beyond your influence.

Second, avoid endless preparation. Plan methodically, account for variables, then cast off and begin. The details will unfold.

Third, maintain a sense of wonder. Awe and inexperience are two sides of the same coin. Resist complacency.

Fourth, be receptive to instruction. Seek out mentors and role models like Jenne, and absorb their knowledge.

Fifth, be humble about your expertise, and even more so about your limitations.

Lastly, never say never. Dreams, even those seemingly improbable Key West dreams, only fade if you allow them to. The journey of learning sailing proves that new horizons are always within reach.

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