We’d never thought about buying a sailboat. Or buying any boat, for that matter.
Nana’s Camp
My grandmother-in-law, affectionately known as Nana, owned a cozy, unheated cabin on a serene lake in southern New Hampshire. In the early 70s, my wife and I lived and worked in bustling Boston. Nana’s Camp became our cherished summer retreat. It offered relief from the city’s clamor and heat. Every Friday afternoon, we eagerly embarked on the one-hour drive, braving traffic, to immerse ourselves in the tranquility that awaited us.
Our cabin neighbored a ski boat on one side and a sailboat on the other. Having honed our waterskiing skills since high school, we relished the exhilarating rush of gliding over the water, surrounded by the spray and wind. The neighbors would arrive at their camp and untied the ski boat. We eagerly lined up, patiently waiting for their grandchildren to take their turns before seizing the opportunity ourselves. Slaloming across the wake and waves provided a cathartic release, washing away the stresses of the workweek.
The Neighbors
The neighboring sailor, on the other hand, had a more serene approach to unwinding. He gracefully sailed his sloop back and forth across the pond, seemingly devoid of worries. I observed him. I saw him leaning over (later discovering the term “heeling”), smoothly progressing without any apparent destination or concerns. Sailing struck me as a more logical method of relaxation. However, my lack of experience prevented me from forming a well-founded opinion.
Unfortunately, due to a long-standing dispute between our families, I never had the chance to be invited for a sail, a missed opportunity.
Discovering Leeway
One mid-summer Friday afternoon, as we drove along Route 3, not far Nana’s Camp, our eyes caught sight of a small yellow sailboat. It rested on supports, with a prominent “For Sale” sign. Priced at $50.00, it appeared to be a perfect fit for the pond. Well within our budget.
Before long, the Snark, an 8-foot, 20-pound Styrofoam craft, had found a new home. We securely fastened it to the roof of our green VW Squareback. Then with wide smiles across our faces, completed the last leg of our journey to Camp.
That day marked our first boat purchase, and we called her Leeway. We chose this name because, under sail, she moved sideways almost as much as she advanced forward. We learned to navigate her in the unpredictable winds of the pond, finding joy in our time spent aboard. But we never thought of her as a true sailboat. We were waiting and someday we would be buying our first sailboat
Growing Passion
This experience ignited a growing passion within us. We couldn’t help but contemplate the possibility of someday owning a bona fide sailboat on a substantial body of water.
Nearly fifteen years passed, accompanied by a mortgage and the joys of raising two children aged 7 and 10. Then we stumbled upon an advertisement for sailboat charters in the picturesque Chesapeake Bay.
For a reasonable fee, we could charter a sailboat. It would come with the requirement of hiring a captain due to our lack of credentials and experience. Determined to embark on this adventure, we enrolled in a couple of weekends of sailing courses in Annapolis. We successfully completed the training. And thus began a decade of blissful summers spent sailing chartered vessels on the Chesapeake.
Annapolis Boat Shows
Our love for sailing matured over time. As our children grew up and ventured into college, I suggested to my wife the idea of buying our first sailboat—a dream come true. For three consecutive summers, we attended the Annapolis Boat Show. There we learned of the available boats, their amenities, and their prices.
Prior to our first two visits, my wife insisted that I leave my checkbook behind. She had not yet been as captivated by the allure of sailing as I had. During those years, I immersed myself in studying everything I could about sailboats. I started with a general overview and then delved into more specific details. Eventually, I had a clearer vision of how, where, and when we would utilize our own vessel.
At the time, the options seemed limitless. It appeared as though we would never reach a definitive conclusion regarding our desires. Lake sailing offshore day passages? A 1,500-mile journey from Annapolis to the Caribbean? Weekends only, full summers, or even living aboard? Racing or cruising? The Great Lakes, the Chesapeake, an ocean, or perhaps the entire world?
A Decision
Based on those choices, we needed to select the ideal type of boat. A sloop or a ketch, a centerboard or a keel, the right length, and the necessary equipment. By the morning of the third boat show, however, I had scoped out our preferences. Debbie allowed me to bring along the checkbook. She agreed to our readiness to embark on this lifelong dream of buying our first sailboat. We even had a name. Second Wind.
Embracing Freedom
And so, armed with newfound knowledge, years of sailing adventures, and a shared passion for the sea, we finally set sail on our journey by buying our own first sailboat. It was a culmination of years of dreaming, learning, and patiently waiting for the right moment. The decision to embrace the freedom and serenity of the open waters brought us closer together as a couple and allowed us to forge unforgettable memories as we navigated the vast expanse of the ocean. Our sailboat became more than just a vessel; it became a symbol of our love for exploration, our appreciation for nature’s wonders, and our continuing spirit of adventure.
