Novice Dreamer to Resourceful, Resilient Sailor
As dawn broke over San Diego Bay in shades of gold and silver, it became a dazzling backdrop for the chaotic symphony of preparations among the Baja Ha-Ha fleet. Our crew stirred sluggishly from their bunks, the air electric with anticipation despite groggy eyes and slow movements. The energy was contagious, yet I took the morning at a deliberate, measured pace — adjusting lines, stowing loose gear, and double-checking systems — much to the visible impatience of nearby crews casting off with practiced precision. By the time we finally shoved off from the police dock, we were the last vessel to join the procession. But fate had other plans. Within minutes, we found ourselves sailing neck and neck with the rally’s legendary Poobah, the unofficial leader of the fleet. Hearts pounding, sails taut, and adrenaline spiking, we surged forward to the front of the pack. The moment was fleeting but exhilarating. Our little boat, Red Beard, had a brief taste of glory before being overtaken by a stampede of sleek yachts and seasoned sailors. As the smallest boat in the fleet, we knew we were destined to play the underdog, but the thrill of competition burned brightly in us. The rally had barely begun, but it was clear — we would push Red Beard to her limits to keep up, determined to prove that the smallest boat could still make the biggest waves.
As the skipper of Red Beard from Portland, OR, I’ve charted a unique course to the world of sailing. With no formal instruction beyond YouTube videos, I started with a 25-ft Lancer — a boat I traded a motorcycle for — and gradually worked my way up to Red Beard, a 32-ft Ericson.
While searching Craigslist for what would become Red Beard, I stumbled upon a job posting for a sailing club. Seeing it as a chance to learn on the job, I took the position, immersing myself in the sailing community. Shortly after, I found Red Beard and moved her to the same marina, splitting my time between refitting the boat and absorbing lessons from seasoned sailors.
Eager for a new challenge but not ready to take on the world just yet, I focused on small steps. A harsh winter, during which the Columbia River froze solid, finally spurred me into action. With eight months to prepare, I made the decision to head south. The clock was ticking, and I was ready to turn years of preparation into the adventure of a lifetime.
Buying an old sailboat can be an adventure filled with surprises, as this story shows. The journey began with a Facebook Marketplace ad for a sailboat named Red Beard. One photo showing over six feet of headroom and the promise of a new Beta diesel engine were enough to spark interest. Without much knowledge about potential red flags, I quickly made an offer and became the boat’s new owner.