Germination of a dream

By Bob White
For Points East

Like so many New England sailors, I have long thought of taking Preamble, my 1998 Island Packet 37, south for the winter. Typically, the idea surfaces while I’m finalizing my fall haul-out and winter storage plans.

guest-bobwhiteAt such times, images of palm trees, sunny beaches and that pretty blue water swim through my head, pushing against thoughts of the coming gray winter with its inevitable snow and ice and bitter cold. I imagine carefree days sailing in warm breezes, snorkeling in clear water, watching for the elusive green flash at sunset each evening. And then, of course, reality crashes the party, and I think of all the reasons not to go: work and family commitments, expenses and logistics, boat condition and equipment needs, just to name a few. This thought process is a yearly exercise for me, and I am sure I am not alone here.

Of course, this is why bareboat chartering was invented. Sure, it’s a compromise, but it’s a pretty decent one: You get the good things you wanted, albeit for only a week or two, and you can avoid the drawbacks and difficulties that would arise from taking off for months on end. While it’s not the same as making the trip in one’s own boat, most years it suffices.

But this year was different for me. I am one year older than last (OK, maybe that in itself is not different, but it sure seems so – more so each year). I just finished up a summertime nine-to-five job that took a serious bite out of the time I spent on the water this past season, and I didn’t have any work scheduled for the upcoming winter. Preamble and I are at the end of our 19th summer together, so she is starting to show her age a bit, but, thanks to a lot of work over the past few winters, she is in her best shape since just before racing to Bermuda in 2005.

So if not now, when? We each have our own, unique mental calculus to do. Being calculus, by definition it changes with time; therefore, it pays to revisit it occasionally. This year, when I looked over the equation again, it all came out differently. It was simply time to go.

Once I made the decision to go, the next question that arose was the age-old one of the voyage versus the destination. Would this be about enjoying the trip south, poking around new places in the Chesapeake, putting in many days on the Intracoastal Waterway? Or would it be about getting somewhere quickly and maximizing the time spent there? Preamble and I are certainly up to the task of a few offshore legs, but how enjoyable would they really be?

More questions soon flooded my brain. Where would I actually go? Florida? The Bahamas? Somewhere in the Caribbean?  What exactly would I do all day, every day? How expensive would it be? How would I pay for it? These questions had all been so easy to ignore when I was only dreaming of making the trip, when I was safe in my inner knowledge that I would not actually go through with it. Now they would have to be answered.

My first thought was to just wander southward and see what happened, to let each place I visited inform on where I would go next. Maybe I could find some work along the way, sell a bit of writing. I am decidedly a voyage person, rather than a destination one, and I am determined to enjoy every part of the trip for itself. Also, I’m not the kind of person who does well with schedules, which only seem to cause problems when traveling by boat. But I recognized that sometimes a bit of long-term structure can actually help, so I have worked up a plan. It is open to change, but, overall, I think it will increase the odds of my trip going well.

I have picked a destination: I am headed for Key West. Probably it would be more accurate to say Key West picked me, or we have chosen each other. In an attempt to answer  some of my other questions about money and what to do all day, I decided to try to put to work my experience and certifications as a sailing instructor, along with my U. S. Coast Guard Masters License.

I sent my resume out to a bunch of American Sailing Association sailing schools and got quite a few responses. A school in Key West seemed the most promising, and the owner of the school and I have come to an agreement about my working there. So, starting in December, I will be teaching sailing courses and running the occasional charter aboard their vessel, while living nearby aboard Preamble between trips.

Meanwhile, that gives a nice, unscheduled bit of time to relax, explore a bit, and enjoy the trip down. I am en route now, Preamble and I having left our mooring in Rockport, Maine, on the autumnal equinox. I am writing this while sitting at a table at Hull Yacht Club, just south of Boston.

I have a bit more writing to do in the next few months. I am finishing up the second of a series of three novellas, and starting the third, and I have a few magazine articles to write. So I do have plenty to do. Hopefully, it is not too much, though, as I want to enjoy the trip down, and also have fun when I get there. And maybe I will see you there.

Bob White, a former high school chemistry teacher, a writer, a licensed captain and a sailing instructor, will write about his cruise for Points East in the coming months. His recent novella, Dead Reckoning, is available as an e-book in the Kindle Store on Amazon. He will be teaching sailing and running charters for the coming winter and spring in Key West (Key West Sailing Academy.) His previous offerings to Points East readers were a mini-cruising guide to Boston’s South Shore in the October/November 2009 issue, and an argument for destination races in the May 2011 issue.