Preparing for the trip north after a balmy Caribbean winter requires careful planning, considering the drastic change in weather. I use a weather app that forecasts my NYC trip’s duration and gives me a comprehensive weather report along the way, including expected temperatures, precipitation, and wind speeds. The app predicts a 6.13-day journey if I set sail today at 8 knots—a passage I envision filled with the sounds of the waves and the sight of endless blue. I’d face the challenge of negotiating unpredictable thunderstorms, their raw power evident in the wind and lightning, and a weather forecast that’s only accurate for 4 or 5 days. After that, anything could happen; a sudden storm, a chance encounter, or perhaps even a miracle.

If all goes smoothly, I’ll arrive within eight days, barring any unforeseen setbacks. I’ll depend on the sage advice of my weather router, Chris Parker, to navigate the unpredictable weather ahead. Three years of relying on his uncanny meteorological predictions, and he’s never once been wrong, not even once. A detailed weather forecast, arriving from him in a few days, will assess the safety of my May 18th departure, considering factors like temperature, wind, and any storm systems. Typically, three distinct weather zones, each with its own unique characteristics, lie between me and NYC. The reliable trade winds from the east transitioned into an eerie calm before the sudden, violent arrival of the cold fronts from the north, a tumultuous change every few days.
So why would anyone willingly endure the pain, exhaustion, and potential danger inherent in this endeavor? This question has haunted me, a persistent whisper in the back of my mind, asked and re-asked endlessly. To avoid hurricane season’s fury, many seasoned sailors store their boats in the sheltered harbors of Granada or Trinidad, south of the hurricane belt. Beginning June 1st, hurricane season arrives with its ominous presence, marked by the rising humidity and the ever-present threat of severe weather. The Dominican Republic sits squarely in the heart of hurricane alley, so to escape the potential devastation, I need to travel either north or south. For 40 years, I’ve enjoyed the practicality of keeping my boat on Lake Ontario throughout the long, hot summer days; the smell of the lake and the feel of the sun on my face make it worthwhile. My desire to head north in the open ocean stems from the thrill of facing nature’s raw power, the challenge of battling fierce storms and unpredictable seas, relying solely on my experience and instincts.
Most sailors, when asked why they brave the unpredictable ocean, struggle to articulate the reasons behind their relentless pursuit of the sea, a mix of freedom and danger that calls to them. Practically, if you want to go somewhere, hop on a plane. It’s a faster, safer, and more affordable option, saving you time, worry, and money. But there’s something truly special about the ocean, a feeling of boundless freedom and the mesmerizing sounds of the waves. The feeling might hit you at 2 a.m., 700 miles from land, a sudden, overwhelming sense of isolation in the vast, dark ocean, the only sounds the rhythmic creak of the ship and the wind whistling through the rigging. It’s a feeling of being truly alive—a vibrant, wild joy—consumed by surrendering to nature’s unpredictable embrace. The world shrunk to the size of a pinpoint, all other matters insignificant in comparison to what you are feeling.
Puerto Bahia Marina
Following a three-week stay in Toronto and a grueling week providing medical care in Guatemala, I stepped onto the dock at Puerto Bahia Marina, the salty air a welcome change. I found the boat exactly as I’d left it, and aside from a bit of routine maintenance, she was in perfect condition, gleaming in the sunlight, ready for our trip. My generator hummed quietly, a steady thrum that suggested it was working well, but I still wanted to check the oil. To be absolutely certain, I carefully reviewed the detailed manual, checking every step. I scrolled to the section and read, “Run the generator for ten minutes before checking the oil level.”
I followed those instructions precisely. After starting the generator, its low hum vibrated through the floor as I removed the heavy soundproof casing and squeezed into the cramped, musty-smelling quarters at the stern. I jammed myself into the generator locker, the metallic scent sharp in my nostrils, and peered as its rhythmic thrumming shook the whole locker. Reaching for the dipstick, I pulled it from its hole, only to be blasted with a shower of hot oil, the smell acrid and the heat intense. Fortunately, I was wearing my glasses. Oil sprayed everywhere, coating them in a greasy, foul-smelling film that blinded me and prevented me from replacing the dipstick. I was so tightly wedged in the generator compartment that I couldn’t find a grip to pull myself out. The oil slick and slippery prevented meaningful movements. A sheen of oil coated everything, the smell thick and acrid in the air. I was lucky… the engine must have run out of oil. I somehow got the dipstick back in, jumped out, and thankfully, turned off the noisy, rumbling generator.
Frustrated, I slammed the manual open; the pages rustling angrily under my fingertips. The part I’d scrolled past screamed in large, bold type, “Never do any work, including checking the oil level while the engine is running!” The stark warning felt like a punch to the gut…….
And I expect to make it to NYC relying solely on my wits?
The other preparations were far less exciting, consisting of mundane tasks like packing supplies. With a grunt, I hoisted the fifteen diesel jerry cans onto the stern of the boat, the sloshing fuel a constant reminder of their precarious placement. I secured them in place with a heavy line. With a push from the boat, I set off in the dinghy, the salty air filling my lungs, to get supplies in Samana.



Hoping the weather cooperates, I plan to set off on my journey this Sunday, feeling excited for the adventure ahead. Martin, my nephew from Guatemala, with his adventurous spirit, is ready to take on the challenge. It will be good to have a clear-thinking mechanical engineering student on board, someone who can offer a fresh perspective and practical solutions when my own wits fail… Will and Will arrive on Saturday, both seasoned sailors, ready for the adventure.
After navigating the traffic of NYC, I will motor up the Hudson, breathing in the fresh river air as I head towards Albany. I will dismantle my mast, carefully loading it onto a truck for transport to Oswego, a port city on the beautiful shores of Lake Ontario. The journey to Lake Ontario will involve a slow, deliberate passage through the 30 locks, each one a unique experience. With a last check of the rigging, I’ll step the mast and sail home across the lake to Port Credit, the wind filling my sails and the sun warming my face. The trip, a three-week journey, promises a transformative experience.
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