So You Want to Buy a Boat

Where do you find the heart of sailing? Is it witnessing both a sunset and a sunrise at sea? Is it in a boatyard with no fresh water, skin itchy with fiberglass? Is it in stepping ashore after a long passage, and drinking sparkling water with a lemon you foraged next to an abandoned dock? Is it in being wet, cold, and slightly frightened? 

Or Is it found somewhere else? Is it found in yacht clubs and private marinas? Is it found in a fully enclosed cockpits with electric winches? Or in that moment you cash in your stocks and buy a boat to sail off into the promised sunset, cocktail in hand?

In the harbor right now there are three boats, including myself, that are all “basically engineless.” Meaning we all have some kind of auxiliary propulsion that only really work under totally calm wind, wave, and current conditions. Whether it be an extremely underpowered 2.3 HP outboard, or an outboard with a shaft that isn’t long enough, or a dinghy hip tied. That means in any and almost all conditions we are sailing, unless it’s for some short stretches of the ICW. 

Is it because we are broke? Young? Idealists? Perhaps a combination of all three. 

I’ve been a vagabond since I was 22 and bought my first boat at 26. I’m 31 now. I haven’t paid rent, except for the odd slip at a marina here and there for a few months at a time, in ten years, and have held various jobs. I happened upon sailing by chance on a yacht delivery in New Zealand and sailed across a literal sea a thousand miles over ten days, and I’ve just been trying to get back to that ever since, on my own boat.

But I never felt stuck in life, in a career, or in the throngs of capitalism that so many people feel that leads them to quitting their jobs and searching for boats. I’ve felt stuck with no money and very unseaworthy boats, but I didn’t do what most of my generation did; which is basically get real jobs. And now that they’re in their thirties and sick of the grind they’re like, let’s get a boat. 

And they go buy some plastic boat from the eighties with a comfortable interior and no inherent seaworthiness in its design, but it’s safe enough. They focus on having a good engine, and then motor across the Gulf Stream to the Bahamas. They follow the “Thornless Path” and motor sail in the calms that can be found in between the prevailing opposing winds. Until they eventually reach the Caribbean and it’s all downwind from there. They have enough money, and enough confidence, even never having never sailed before, that they make it just fine. 

Lots of people do this, especially with the advent of YouTube. People are like, “Yo, I can live on a boat and make a YouTube channel to pay for it?!” 

But I can tell you this is not where you will find the heart of sailing. That is something you really have to look for. This is where you will find a departure from it. I’ve been trying to find it for years by now of living aboard and messing around with boats, and I still know nothing. “Remember you know nothing,” an old schooner captain told me. That’s what makes you a good sailor, he said. A good captain.

Famous sailor Nancy Griffith said, “know the limitations of your crew and your boat.” Crew, for the most part, has usually been only me. And I’ve scrutinized both myself and my boats heavily when weighing certain passages. I worked at marinas as a way into even learning about boats. My first boat I stuck to lake Champlain, my second I took down the Hudson River and to the Florida keys, only spending a little time offshore. The boat simply wasn’t prepared for passage making. Most of the offshore sailing I’d done before my current boat, was on boat deliveries. So I hold myself to that standard of seaworthiness, of what I’ve seen on the sea. 

I spend more time fixing my shit to be at sea then I do actually at sea. I have to fix boats so often because I don’t have money, so I’m pretty DIY. The trouble is I really don’t trust my work. I rely on people with much more skill than I have to tell me if I’ve done something right. For me, the goal is to make my boat as safe and comfortable as possible on the sea. It’s been and continue to be arduous, refitting old boats to be sustainable in such an inhospitable environment, with little money and no formal training.  

Sometimes I envy the other kinds of travelers. The backpackers. The ones who hoof it, bus it, ride planes and hop trains. But that’s not for me. Devoted to the sea. And if I can’t be there, damn it, I’ll be on land just trying to get there… because nothing else matters. 

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Tropical Depression

There’s a tropical storm bearing down and it’s about to clip my anchorage. I wasn’t going to write this on the internet anywhere so my parents wouldn’t worry. But they found out about it on their own accord. I’ve got two anchors out and am protected from the wind direction in this harbor. It’s not expected to blow any worse than a winter gale, but still, it’s a bit early for this nonsense. I’m further south than I’d ought to be this time of year, but I thought I only had to worry about the heat and thunderstorms the further we marched into summer. This time last year I’d just barely arrived on the Chesapeake Bay by now. Tropical Storms were the furthest thing from my mind. Sean was still three weeks out from sailing north around Hatteras. This is the time of year people sail to Bermuda and cross the Atlantic. It’s not supposed to be like this. It kind of snuck up on me without warning. Whether it was fast moving or I simply wasn’t paying attention.

This changes everything. I was planning to cruise the sounds on my way north stopping at different islands for anchorages. Taking about a week to meet up with the inland waterway and then follow that into the Chesapeake Bay. Now I’m not so sure. With the potential for tropical storms and hurricanes to become threats in a matter of a day or two notice, I’m wondering if I should seek the protection of inland waters sooner. I don’t have a large diesel engine that I can just crank on two days before a storm to guarantee miles. I’m at the mercy of the winds.

Speaking of diesel engines, I ripped the one out of this boat and sold it in a quest for simplicity and to pay for my refit efforts. I’ve sold enough gear off this boat now that I got her for $1000. And let me tell you, it’s starting to feel like a thousand dollar boat. I’ve had to redo damn near everything. Through hulls, coamings, standing rigging, chain plates, etc… etc.. I find it troubling that the only thing really of “value,” on the boat, was the diesel engine. That’s what people consider essential. It didn’t matter that the rigging was precarious and all the wood in the cockpit was rotted, or that the through hulls were a terrifying corroded mess of antiquated parts…it mattered that it had an engine you could just fire up and “go.” How far have we come from what is considered essential, and seaworthy? When did it become engine first, then rigging? How many people if you ask, what is the heart and soul of their boat, would say their inboard engine?

Sean has moved off the boat and onto his trimaran. So, I’ve effectively had this boat on my own now for one month. I bought the boat through love colored glasses and we both had dreams to fix it up together and cross the Atlantic. With him I really thought it was possible. But it turns out love isn’t always enough. I realized that I stopped wearing my harness and life jacket when Sean came aboard. I stopped caring about a lot of shit.

He’s the kind of person who can manage to fucking circumnavigate on a boat that was basically derelict when he got it. With the right amount of luck, a great deal of intelligence, and an amygdala that doesn’t register fear and risk in the same way as neurotypical people—he fixed it in mostly all the right places and transitted the fucking planet. Not only is this a feat most sailors and people will never achieve, but he did it probably in one of the most uncomfortable ways.

No bunk. No sink. No standing head room. He told me roaches used to eat his toes at night on passages. I thought he was kidding. I always used to think he was kidding. His boat was a mix between some mad scientists lab and Davy Jones’ Locker. He just laid down on a bunch of wires to go sleep before I met him. All the way across the seven seas–passing the time alone contributing source code to open CPN, a navigation program used by world cruisers, and designing and manufacturing his own auto pilots

I should have known better than to disturb this delicate creature. Because here we are now. It’s funny how someone can go from your hero to your ex that you have petty arguments with across the harbor.

It turns out the “Go North” and the “Go Offshore” are two entirely different lists. The former I’m almost done with and the latter I plan to finish on the Chesapeake.

There’s nothing left for me here.

I’m still not sure how that story ends, so it’s a good thing the submissions deadline for my anthology project Heartwreck: Romantic Disasters at Sea, has been pushed back. More info on submission guidelines here. New deadline is TBA.

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