The sound of gear crashing around thundered from below while the noise from the 60-knot gusts screaming through the rigging put our senses on full alert. Trying to look forward beyond the cockpit was useless. Each stare was only met with stinging rain and swaths of saltwater flinging through the air. I looked down at my friend Suzy, who was trying to make order of the cockpit. She was looking at me attempting to figure out if we were in real danger. I gave her a reassuring look, and said, “Don’t worry, the boat can take it, we’re going to be fine.” I was trying to be as calm as possible. But inwardly, I was screaming for putting my friends and boat in this situation. I should have delayed the departure. I should have prepped the boat better. I should have done more than a few things differently.

I certainly have experienced similar episodes during the last 20 years that I would prefer to forget. They are usually the result of a lapse in judgment or perhaps a case of inexperience. I’ve chronicled several in the pages of this magazine. These have only added to my skill set, as I try to learn from mistakes. This trip, however, left a dark, permanent stain on my psyche. I continue to dissect the events to this day like an over zealous NTSB investigator. Besides some marginal judgment, it involved horrendous bad luck, brought on by a dark shadow cast over our boat by a crew member whose name my lips shall never mutter again. A name—that if mentioned—would surely unleash a monsoon filled with locusts and frogs. For the sake of this article, we’ll call him Jim, or as he was known during his tenure on board, The Black Angel of Death.

The trip had the making of a paradisiacal cruise for me and my good friends, Jack and Suzy Bulger. We were going to deliver a 44-foot sailboat (yes the editor of a powerboat magazine also sails) from the Virgin Islands to Antigua where another group was planning to charter the boat. “It’s going to be great,” was how I started my sales pitch. “We’ll head up to Virgin Gorda where I got you a room at the Bitter End Yacht Club, and then we’ll have a better point of sail down to St. Barths, and then down to Antigua.” I explained we would leave plenty of time to enjoy the sights, and make this a leisurely cruise, versus a straight delivery. They were eager to leave a New England winter and jumped at the chance.

I knew the boat had a tough year, that included two trans-Atlantic crossings. Trying to be a prudent captain, I sent a list of questions and maintenance requests to the owner. It included basics like servicing the engine, changing the oil, cleaning the bottom, safety gear questions, spare parts questions, and so forth. The owner said he would address everything on the list. He also asked that I bring along his employee Jim, in an attempt to get him more time on the water. (He’s in the marine business.) No problem, I thought, not wanting to be a third wheel on what I was hoping would be a romantic getaway for Jack and Suzy.

Jim and I met up at JFK for the flight to St. Thomas. I asked if the owner had worked on the boat as we discussed. “Oh yeah, I got your list right here,” he shot back and presented a crumpled piece of paper with tomato sauce finger prints smeared all over the place. Scribbled next to each item below the Ragu was some type of illegible calligraphy. Although next to the major items it appeared the word “yes” was written in the column. I assumed that this met “yes” the work had been done. This was one of the first mistakes I made. Several days later, I realized he just meant, that yes, this would have been a good idea! Never, ever, assume anything is done. Make sure you verify.

After arriving in St. Thomas, Jack, Suzy and I began provisioning, while Jim went to a storage container to get a variety of gear, including delivery and storm sails. He showed up six hours later for an errand that should have taken an hour. This delayed our departure by a day. He was ranting about getting lost, then winding up in a bar somewhere. I never fully comprehended his tale, but I wouldn’t be surprised if there is a mob of irate locals still looking for him today.

The next morning, I shaved a few items off of my shopping in an effort to make up for lost time. Of course, everything that I didn’t get, we desperately needed during the course of our trip.

Only hours out we were powering into a strong head wind and the engine came to a wheezing stop south of St. John. We managed to sail onto a mooring in an idyllic cove and began to address the problem. The fuel filter appeared clogged, which was one of the items on my list! There was also air in the system, and had I bought the jerry can of diesel like I had planned, the bleeding process would have been easier. In any case, after several hours, we managed to restart the engine. However, this put us further behind, forcing us to bag the idea of going to the Bitter End Yacht Club. Instead, we spent the night on the mooring, and pointed our bow toward St. Barths the following day.

In the end, this turned out to be one of the biggest mistakes. The track from the Bitter End to St. Barths was a much better point of sail. Now we would have to tack into the dominant tradewinds for more than 120 miles. Had I sacrificed the time then, we would have probably gained the 24 hours we wasted trying to sail into 30 knot winds.

Furthermore, we lost the engine again while charging the batteries, and to top it off, our boat was engulfed by squalls with winds in excess of 60 knots throughout the day. “That’s right George, a leisurely cruise through the islands, fine dining, blah, blah, blah,” bellowed Jack, while taking the helm during one of the squalls. While Jack was at the helm, and Suzy was taking care of the sails, I was busy navigating. Although the boat had several thousand dollars of electronics, including autopilot, radar, chart plotter, SSB, and instruments, nothing worked! I was back down to my $150 handheld GPS and paper charts. We later discovered wiring issues when we arrived in Antigua, brought on by a series of leaks.

Jim, who I will say was filled with good intentions, spent this day basically falling on the rest of us, and usually impaling us with a heavy object. After I was whacked in the spine with a winch handle for the fourth time and my back went numb, I stopped complaining.

Every time we changed course, so did the wind. It was uncanny. We surrendered ourselves to a long night at sea. We decided to switch to the smaller foresail before the sun went away. I prefer not to be on deck for a sail change in heavy weather during the night. I went down and grabbed the bag that Jim brought on board. Imagine my surprise when I opened it, only to find an awning stuffed inside, not a staysail. Jack simply glanced at me with a smirk when he saw the bundle of useless moldy canvas.

We turned off the fridge to conserve battery power, but I never picked up the ice. I ran out of time in St. Thomas and had planned to get some at the Bitter End. So now, all of our food was going bad. That next morning, I hunkered down around the engine in a cabin that had to be more than 90 degrees, trying to solve the engine problem. (You better believe I was thinking about doing this trip on a well-found powerboat right at that moment.) The tool kit was basically a tray of rusted wrenches, a screw driver, and a hammer. (Item number 4 on the list was to inspect the tools.)

I discovered a hairline crack at the bottom of the sight bowl valve on the fuel filter, which was leaking fuel and allowing air into the system. I mixed some epoxy and decided to do a crude repair that would at least allow us to run the engine. Jim, always eager to help, grabbed the valve off the table, and began twisting it. “Jim, please don’t do that,” I said, as if I was speaking to a 5-year-old. “I just want to see how this works,” he replied. Just as soon as he said that, the entire assembly snapped in his hand! Now I had a one-inch hole in the bottom of the bowl! Jim went into a rant, hitting and screaming at himself. Uh oh!

I went back on deck to get some fresh air, leaving Jim alone to punish himself. I gazed out over the rough, endless ocean, while Jack and Suzy sailed the boat. I wondered how once again I got myself into this situation. You see, a lot of boating magazines will only talk about the good times. But that’s not boating. There are times when our decisions put us in uncomfortable spots. Isn’t this one of the definitions of an adventure? That once you’re experiencing it, you’re looking forward to it ending. Then once it ends, you realize it wasn’t that bad and plan the next outing. In my case, a lot of the issues could have been avoided if I just followed my gut, and took the measures that I knew were necessary for a safe and more comfortable cruise. Had I reviewed the list directly with the owner, I would have realized that the boat was not at all ready to go. Or, if I took a breath and laid out a new itinerary after Jim’s disappearance, I could have avoided the weather and left from Virgin Gorda, the better port. If I had taken the 25 minutes to load up on ice, my crew and I would not have been eating saltines and peanut butter for dinner.

I tend to operate in a Type A flurry at work in order to get our magazines out the door. It’s part of the publishing business. However, I now know that when it comes to boating, a slower deliberate pace is necessary when planning an extended cruise.

Eventually we did make it to Antigua, without an engine, electronics, decent sails or a refrigerator. The boat developed a few leaks, that combined with the shallow bilge, meant we had water sloshing around our feet the entire trip. During our overnight in St. Barths, Jim proceeded to drink like a fish. I’m not casting stones in a glass house, but even I was a bit embarrassed. He also decided that personal hygiene was not important and had not showered for days.

After securing the boat in Antigua, Jack, Suzy and I decided we desperately needed to get off the boat and take a spell from Jim. We threw our gear on board the water taxi like we were fleeing a burning building. Because it was the annual race week, all the hotels were booked. “But I do know of a house for rent,” said the Yacht Club concierge. “But, you don’t want that, it’s a $1,000 a night.”

“We’ll take it!” said Jack without any hesitation. Less than an hour later we were floating in the pool, while sipping on a rum punch. “You know, that really wasn’t that bad,” Jack said.