After crewing on the 2015 Caribbean 1500 rally, I bought Gryphon, my 1993 Morris Justine 36, with a specific goal in mind—sailing from Maine to the Virgin Islands, with pit stops in Annapolis and Portsmouth, Virginia, where I would join the Caribbean 1500 for the last leg. Gryphon is not my first sailboat, but she is certainly my first ocean-worthy boat, and this would be my first serious voyage as skipper of my own boat.

The prospect of sailing 1,500 miles, up to 400 miles from land, in a boat that was new to me made me focus on my lists of proactive maintenance and system improvements every day for six months before departure. Despite this intense focus, I was still not able to learn what I needed to make the voyage until I actually made the voyage.

While my learning curve was steep in the months before the trip, it became even steeper once we left the dock. The intimate understanding of a boat that is necessary to prepare her seemed only to come to me after situations in which things were not working correctly. I read as many books as anyone could, and I asked questions until I feared I had become a pest. Still, I needed to go out there and have parts or systems fail and then fix them before I understood them sufficiently to go offshore with them. The way I would prepare for going offshore was by getting beaten up offshore.

For example, there is a tangle of wires behind the companionway concealed by a panel that takes some determination to remove. I did not appreciate what was going on in there until the autopilot and GPS quit working early into the Gulf Stream crossing. The only clue to the source of the failure was an accessory display for wind and navigation data that read “insufficient voltage.” We called Morris Yachts Service for advice; they suggested we use our multimeter (“I’m assuming you’ve got one?”) to track down a presumed short circuit. By the time we found the short, we had tracked most of the wires from that tangle to all over the boat. You could say I prepared for the GPS failure by having a handheld and buying a new fuse for the multimeter before we left, but I only began to understand that system once I had to fix it.

My system for spare parts storage had consisted of several garbage bags that were gradually getting ripped apart by their contents. On the passage from Maine to Portsmouth, I accessed these so often that by end of the trip I had the parts organized into bins repurposed from my children’s onboard toy collection. Among those spares were several extra fuel filters the chief mechanic at Morris had thrust into my hand at departure. When the engine quit and we saw what looked like phlegm through the filter glass, I pulled out the books and figured out how to change a filter.

My understanding of what to do in high winds followed a similar pattern. Not until I was in them did I become convinced of what I needed. The serene waters of Maine where I had sailed with my family most of the summer, gunkholing between Northeast Harbor and Camden, had lulled me into a sense of security with my existing sail-control systems. A sled ride from Annapolis to Portsmouth, by myself in 35-knot winds, moved a few things higher on my priority list. All summer, I had debated whether or not to install running backstays. Deploying the staysail in that much wind showed me how much the mast can pump when a force pulling at its midpoint is unsupported by running backs. At least I learned while I was still in the Chesapeake Bay.

Before those high winds, I figured I could get by with “work-arounds” rather than secondary winches. Work-arounds are fine until stuff hits the fan and you need all the mechanical help you can get. I realized I couldn’t afford to save the money when I was up on the bow trying to manage the disaster created by failed work-arounds. I had to turn downwind to keep the headsail blanketed by the mainsail, but as I was running out of sea-room there wasn’t enough time to set up the clunky preventer system and when I watched the boat gybe, there was nothing I could do but hold on.

I needed the ability to control lines with enough redundancy to manage multiple things at once. A situation might start with just one thing going wrong, but that can very quickly escalate into several things going awry if not brought under control.

I continued to find the need for upgrades right up to the time I departed, almost to the point where they compromised the overall management of the campaign. I had the boat hauled out of the water in Portsmouth to inspect and repair the keel because I had hit a couple of rocks hard on the way down. We launched as soon as I returned and I was back to my lists. The biggest job was installing those secondary winches and I thought I had everything set to go until people started telling me I needed backing plates, making the project complicated to the point where it almost did not get done.

Boat projects always seem to have complications and extra considerations that make them take longer. I was blessed with a crew member who could take on projects independently and I took full advantage of that. The safety inspection found some deficiencies we had to address, I needed charts and we had to provision the boat with food for twice the length of our anticipated trip. I was determined not to leave the dock with projects we still needed to do, having learned my lesson by leaving Maine with work undone.

Mechanically, I suppose things worked out alright. We got our autopilot back once we figured that the short was in the GPS antenna cable and that all we had to do was disconnect it, and we felt pretty smart. But now we were tired. For a full day we had hand-steered, one man always at the wheel, with waves the size of the sledding hills at home in Minneapolis, while the other two tried to get multimeter readings in inconvenient places. A couple days later we found the actual frayed spot on the antenna cable, which could only be seen using a mirror and a flashlight, and bypassed it so we could use our electronic navigation again. We were on a roll. We got the engine running again when it quit and I learned how to bleed fuel lines while wedged in a corner to keep from being thrown around. I kept devising various rigging experiments, like my continual improvements of the preventer system. Until the boom’s gooseneck broke we had been able to fix most things, and even then we had enough fuel in jerry cans to allow us to motor-sail the rest of the way to Nanny Cay without a mainsail.

But the challenges of open-water sailing go beyond figuring out how to control the boat and keep it going. I also needed to manage a crew. Early on, I did not appreciate how important it is to clearly communicate the way in which I wanted things done and maintained. Lines have specific uses and sometimes need to be employed immediately and I do not want those lines used for random jobs. Equipment storage is tight and moving one item can create a domino effect of other items being moved. The set-up of a sailboat is part science, but part art, too and this blend of art and science creates a system. Well-meaning deviations from that system by new crew can have repercussions that break it down.

Before I had a chance to even consider those issues—I was having a hard time just finding crew. Without crew, I would not be able to sleep, so I wanted at least one person to sail with me and then decided I needed two in case someone got sick or hurt. By October four people had backed out and another turned out not to be a good fit. Each time I was down a person I was left slightly panicked about who else I could find. I was asking people to take a three-week trip out on the ocean with a captain new to ocean sailing and on a new boat. My list of friends to call was getting short.

I could certainly tell prospective crew that Gryphon was a well-built boat and that I had taken every step to make her safe, but I was also aware that I might not be offering the level of modern conveniences that some people expect on a cruising boat.

My personal taste is to have more of a wilderness-out-in-nature type of experience than a pampered one. I chose and equipped Gryphon accordingly. She is a strong seagoing boat, but she is also small, which means that the area where the people live is closer to where the sharks live. There is no shelter behind which to steer without being exposed to the elements. We have an autopilot and a new electric refrigerator so we are not living primitively, but I do not have a microwave and cannot run a hair dryer, much to the surprise of some prospective crew. I crank my anchor up manually. I have an electronic navigation system but prefer to use paper charts.

Prior to departure I worried about losing crew, and became frustrated as I realized that my dependence on crew cut into my coveted independence. By the time we started I had become excessively accommodating. I would not speak up when we dropped below my standard of neatness. I did not enforce equality in cooking or cleaning. I agreed to fishing late in the day just as conditions were about to deteriorate. I let people change where things were stowed. I let myself be convinced by the crew to leave the dock when we weren’t ready, based on an assurance that we could get things done underway. As we approached Tortola I was going to risk making landfall at night, cutting through some narrow channels, because my crew had been counting the hours until our arrival. I succumbed to pressure in how much we ran the engine. I took chances with the crew, like letting someone steer with the spinnaker, which developed into a situation in which I thought we could lose the mast 400 miles from shore. Worst of all, I deviated from a safe course to one that was much more dangerous when a crew member threatened to leave the boat if I didn’t, and I was going to keep that crew even after he openly questioned my role as captain.

I am not particularly interested in being an authoritarian captain, but I can appreciate how that tradition came to be. With a new crew on board routine has to be enforced. Also, it takes a considerable amount of confidence to captain a boat. Threats to my confidence make me less able to see solutions to problems. I was already uncertain of my own ability.

Interestingly, I think a friend was trying to help me with just these aspects of preparation in the weeks before I left. He recommended some reading and I was surprised that it dealt with how to run sailing campaigns, not about actual sailing. When he talked to me about my preparation he asked me about my watch schedule, concerned about how we would get rest, maintain active roles and facilitate communication. I thought he still needed to teach me about technical stuff like the wind speeds at which I was going to reduce sail. The year before, I had noted the measured intensity with which other captains had approached the days before departure, and was aware that my busyness was making it hard to achieve that level.

We finished the Caribbean 1500 at the back of the pack, which was expected as we were the smallest boat in the fleet. But I’d thought my childhood of dinghy sailing and a more recent history of keelboat racing might help us keep up. I learned that people who have done ocean sailing know how to keep their boats moving.

People tend to assume I would feel a sense of accomplishment, but more than anything I was humbled by the experience. I needed to do all the preparation that I eventually did, and I needed the pressure of the trip to force that level of preparation. But no matter how much I prepared the boat, I was not going to be prepared for a cognitive and emotional challenge in one of the most remote places on earth until I had done it myself, in my own boat, responsible for all major decisions. I could have hired a captain or stayed close to shore, but had I not done this trip the way I did, I would never have known how much I didn’t know. 

In the first year he owned Gryphon, physician Dr. Walter Rush cut back on his practice and spent 95 days onboard—at his wife, Kate’s, instigation!

January 2018