The Long Way to Key West
Sailing the world has not always been a dream of mine. In fact, I would confess that most of my life I had no clue what sailing even was. The idea that people lived on boats was hardly one I could imagine. Sure, a cruise ship or an aircraft carrier made sense to me, but someone floating on the ocean, using nature as an engine, coasting across the Atlantic? That was an idea not seen in my wildest dreams.
Despite my lack of knowledge, it would seem I was meant to learn the ways of the sea. At the age of 25, I recall chancing upon a YouTube video that would shake my very existence. It entailed a young Frenchman taking his 28ft sailing vessel from Europe to America, or to “hop across the pond” as they say. The thought of a single person navigating across an entire ocean would set my mind spinning.
Thus a seed was planted, and a dream was formed. I would learn the ways of the wind and seas and I too would sail to shores unknown. And now, after five years of sacrifice, moving from mountains to coastlines, and many hours of effort, I get the chance to leave the safety of home for adventures unwritten.
Despite purchasing and living on my own sailboat, it seemed the vision of new horizons only distanced itself with each year. Personal issues, boat projects, and of course finances all seemed stacked to keep me in port for the unforeseen future. Still, I vigorously continued the work of honing my new craft of sailing.
It was in late 2025 that an opportunity arose that I had not foreseen. A close friend had decided he was ready to sail his own boat from Charleston, SC down to the Virgin Islands. His only reluctance being that he did not want to go alone. Suddenly the horizons grew much closer.
Off into the great blue
The sad reality was that my own boat still had a long way to go before being sea-ready. With some reluctance, but also rising levels of excitement, I moved on to my friend’s vessel and began the preparations for departure. We had several months of work that needed to be done and set ourselves to the task.
By mid-January, we felt the pressure to leave mounting. Knowing the preferred season to head south was passing us by, we were called to action. The rigging had been replaced, sails mended, and oil changed. With neither of us having completed a passage of this length, I endeavored as well as I could in the ways of provisioning, route plotting, and weather tracking so that all would be smooth seas.
When the fateful day arrived, we finally pushed off the dock. Despite countless hours of experience gained over the past years, my stomach was aflutter. This would be my longest offshore journey, and I was the designated captain to boot. The joy of a dream turning to reality was palpable. Little did I know of what lay ahead.
As my friend and I set off, our first destination would be that of Fort Lauderdale. A convenient launch point to reach the Bahamas, which would be a major aspect in reaching our ultimate destination. Anticipating only a handful of days for this leg, morale couldn’t have been higher. It would not take long for the two of us to realize the boat was not as prepared as we once believed.
Our first hurdle met us in the first days offshore. A vital breaker switch had not been turned off when leaving shore power. The result was soon realized as our batteries had been blown through. Although we had solar power, it was not enough to offset the power draw we had not recognized.
This would cause us to discover a new issue. Our alternator was not generating power. With our batteries well depleted and food going bad in a now dead fridge, we diverged to Saint Augustine. A stop not in the original itinerary, but one of many in the unforeseeable future.
In spite of these issues, our first nights at sea were serene. Getting to feel the lurch of the swell beneath my feet. Seeing the sun go down and watching her come up with nothing but ocean to surround us. These were moments not soon forgotten. It was a dream come true, yet reality is never as clean as the dreams we imagine.
Somewhere in the Atlantic
Within a couple of days of anchoring, parts were replaced, and once again we were back out to sea. Resuming our path to Fort Lauderdale, nothing could stand in our way. Well, besides the fact that the wind and tide moved directly against us. We began to realize our short hop down the coast was going to take longer than anticipated.
Once again, we found ourselves passing through the deep blue. Even though we had no autopilot, coupled with the fact we were running three-hour shifts between the two of us, I still discovered a deep sense of peace being miles from land. Suddenly there was no distraction of social media, problems at home were far away, and my spirit could simply enjoy the peace of the waves and wind rolling through.
Although the mood remained upbeat, the lack of sleep and our slow pace began to take its toll. Our wide-beamed 42ft ketch was anything but quick. The estimated schedule we’d crafted quickly began to evaporate, and with weariness setting in we once again shifted our course. Setting sights on New Smyrna for a brief respite and full night’s rest.
As we began approaching the inlet, with myself at the helm, there rose before the bow two massive rocks breaching the surface. Shouting my dismay, I hurriedly cranked the wheel to port, bewildered that such a tower would reside where it did. Yet it was nothing inanimate that swam beside us. Looking over toward the dark shapes, her eyes locked with mine.
What had breached before us was in fact two North Atlantic Right Whales! With one being massive and the other of a lesser size, I surmised it to be a mother and calf. My excitement was at a crescendo. While I continued to point our ship out of their apparent path, I couldn’t contain the delight from my face. What an adventure I had set out upon.
She was there, I promise!
I could go on about stopping in New Smyrna. How we fished and slept at our anchorage for hours. Or how I was dingied to shore with my surfboard in hand to rip the waves. But just know, the little boy inside me from Cocoa Beach, FL had his stoke on.
With the anchor raised we once again set out for Fort Lauderdale, a land that we desired but seemingly could not reach. And that was not about to change. You see, as we slowly carved our way down past Cape Canaveral, we would be assaulted with a barrage of issues.
It was closing on midnight when I was finally able to lay my head down amidst the rocking of the ship. Just then I heard a loud “snap,” from the engine room. I knew something to be wrong and shouted for my crewmate to shut off the engine. Upon investigation, it was discovered our coolant belt had snapped in half.
Zach passed me the wheel with assurances that a spare belt would be on in short order. As it would turn out though, none of our spare belts would fit. With him growing sick from the waves and fumes, I soon had him resting knowing I could not afford to have both my partner and engine out of commission.
Fortunately we were on a sailboat! Sadly, she is beamy and has little to no ability to point upwind. With conditions blowing almost directly from the south, we were in for a long, slow, crawl. Tacking far out to sea to only track slightly farther south was a wonderful lesson in patience and monotony. Did I mention we had nearly 20 hours of zero wind while we drifted north?
This is not to mention that our mainsail had begun to tear something fierce, further inhibiting our already “speedy” cruise south. I was beginning to feel how impossibly far away the Virgin Islands really were. After four drudging days, we crawled into Fort Pierce, FL to make further repairs.
Decisions needed to be made. Our pace was clearly far from desirable and the idea of doing much more open ocean sailing was seeming more and more foolish in recognition of the state of our vessel. Taking the lead, I made the call that with our current resources it was time to pivot. We would hop into the Intracoastal Waterway and make our way down to Key West.
One of my favorite anchorages of the trip
It would be easy at this point to feel discouraged, to seem foolish or naive in the decision to leave home, but this is the adventure! The dream is being realized, it is only a matter of going where the wind blows. To quote Lord of the Rings, “It’s a dangerous business, Frodo, going out your door. You step onto the road, and if you don’t keep your feet, there’s no knowing where you’ll be swept off to.” With that mindset, we kept moving forward.
After fixing our belt problem, we continued traveling down the waterway to reach our elusive destination of Fort Lauderdale. But with the crossing out of the question, we continued heading south through the city. This would be the least enjoyable chapter of the whole journey. The stress of weekend traffic, waiting on bridges, and being surrounded by the curmudgeonry of busy cities weighed on me.
It was not until we passed through Miami and into Hawk Channel that my heart came back to life. Witnessing the beauty of the Magnificent Frigate birds gliding above paired with the untouched sense of nature surrounding was a beauty to behold. This would also be my first opportunity to anchor in the seemingly open ocean. A small key on one side with the entire Atlantic on the other.
As we made our way we would stop and moor amongst the protected reefs. Gracing us the opportunity to snorkel and dive amongst the ocean's beautiful life forms. It seemed I could not hold my breath long enough as I encountered the rainbow-covered parrotfish and schools of lovely silver fish. Even above water the beauty continued, taking in the divine orange and pink colors of sunset sighing down the horizon.
Sailors would know and expect that there were many more issues that arose on this trip, but that of course is all a part of the beauty of sailing. Leaving old comforts behind it was an all too short two months from Charleston to Key West. I learned more than a book could teach, saw sights people dream of and overcame many adversities. Now safely at anchor I have rested and recovered, and I cannot help but ask when the next journey will begin.
When heavens comes to earth
