Sailing For Love and Money
- Joy Sherman
- Jun 30, 2019
- 4 min read
A lifelong sailor supports her passion by chartering, Good Old Boat - July 2019
By Joy Sherman
It was 2004 when I entertained the thought of a boat of my own. I had just completed the exam for USCG Master. When I took the exam, I had no intention of buying a boat, let alone opening a charter business. I went for my license purely for the end result. I had just come out of a four-year relationship. We had sailed and lived aboard his old schooner. I can say with caution that it was a great experience, perhaps the closest idea to my perception of bliss. But nothing’s perfect and, as wonderful as it was, there was good reason for moving on. I had put a lot of time and much effort into that relationship and his boat. At the time of our breakup, not knowing why, I made sure I walked away with a good record of my sea time.
During this personal transition I was a full-time employee at a local Ivy League university. It was a good job with good benefits, but the everyday lacked the passion I’d always read about others feeling who followed their hearts. Believing that everything happens for a reason, shortly after I got my license my father told me he’d found the perfect boat for me. My thoughts morphed from “Huh, what? I don’t need a boat…” to “Hmm, interesting.”
“Why get your license if you’re not going to use it? What’s your plan?” he said. (With him, you always had to have a plan.) “Why not start a charter business?”
Why not? I had crewed on private yachts for several years out of college. I’d served wine and well-prepared meals to many a distinguished guest, traveled to exotic destinations aboard fine yachts, and got paid for it. Great customer service was not a cliché; it was imperative for success as it is in any service field. I had accumulated years of sailing and boating and customer-service experience, it’s true, but I also yearned for something new and creative, something that wouldn’t take me away from the long-term predicament of my 9-to-5 job and back to sailing regularly, meeting new people, and experiencing some awesome sunsets. To be clear, I continued my 9-to-5 job. To do that, I logged hours doing something I loved to do.
After taking a look at my father’s idea of the perfect boat for me — an easy-on-the-eyes, seaworthy boat — I cautiously fell in love. She looked to be in great shape, which was a good start. Further inspection, however, revealed she was in need of new decks. The balsa core was wet. Repairing it was a big job, but the insurance company would not let me charter the boat until it was completed, so I made it part of the negotiations. Within a few days I became the proud owner of a sweet 1963 Pearson Alberg 35.
A business takes shape
That was in October 2004. I had most of the winter to take care of the decks and other facets of this new business, including a logo, website, business cards, and marketing. The website was by far the hardest of all the tasks. Writing is easy for me, but thinking about how to fill the pages of a website was a daunting task. In spite of this, the passion unleashed in me by the idea of sailing again and getting paid for it lit up a drive that found me working late into the night on this business venture.
I had to come up with a marketing plan, and I attended many chamber of commerce and other business meetings to tell as many people as possible of my new undertaking. I had decent experience with computers but was no expert, yet with some online instruction and time, I was able to create my own website. At a free small-business meeting, I learned about the technical part of hosting and page rank that proved to be invaluable.
Over the past 10 years, my business, Joyride Charters, has steadily grown. It’s been a constant effort to look for new ways to expose the business to different markets and keep up on social media.
I recently redesigned my entire website. I had to make the dream continue to work. Five years ago, I made more room for sailing by switching to a part-time job at the university. Note that I still haven’t given up my day job. And further still, I’m in the process of reinventing myself and my captaining gigs yet again. This might include selling my beloved Hado.
If you’re thinking about becoming a captain and chartering your boat, I highly recommend you do it for the fun. Although you surely won’t make a living at it, you should be able to pay your charter business expenses, including upkeep of your vessel. What could be better than having your habit paid for?
It takes lots of patience and sweat equity to maintain a boat and run this kind of business, so do it for your love of sailing. Any sailor will tell you, it’s about the journey… not the destination.
Hado, needed a fair bit of work before Joy, below, could put her into charter, but her classic looks and ease of handling make her an ideal platform for showing people the pleasures of sailing.
Joy Sherman learned how to sail and drive powerboats from the age of seven. As a child, she lived aboard her father’s 60-foot wooden powerboat in the Bahamas and Miami and was even driven to school in a Boston Whaler. She worked summers restoring wooden sailboats and, after college, signed on to a 130-foot converted Danish hospital ship as a stewardess. For four years she traveled from Maine to Florida and the Caribbean, working aboard large luxury yachts as stewardess, chef, and first mate, experience that years later helped her obtain her USCG Master 100-ton license. Since purchasing Hado in 2004, Joy has been in business as Joyride Charters (www.joyridecharters.com
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