There are moments when small things go wrong on the boat.

There are moments, too, when you look at the weather and the seas and you say, to no one in particular, No, not today, and your boat stays where she is. I have met boats that forge onward through any weather at all, boats that hide from every shift of the wind, boats going west with the trades and boats heading east right into their teeth. Everyone dances to their own beat.

It was that into the teeth part, specifically around Cabo Beata, Dominican Republic, that helped me end up in rainy Jamaica. I was sick of fighting my way into the trades. I was sick of motoring and motor-sailing and pinching and wind in my face. The day that I was supposed to sail east from Haiti towards the Dominican Republic I called my friend and buddy-boater Aldo on the VHF.

“I can put my dinghy in the water and come to you, or you can put yours in and come to me, but we need to talk,” I said over the handheld.

“You stay there,” he replied. “I will be right over.”

This was part of buddy boating that Aldo and I did really well together. We knew how we communicated well and how we communicated less well, and face to face was the only way real decisions got made.

Aldo was soon on my boat, sitting in Ave del Mar’s salon. I told him that I didn’t like the forecast, I didn’t like the winds, I didn’t like the seas, and I would not be sailing east, at least not that day. As always I reminded him that he was free to go without me. That got tossed right out the window. “If you do not want to go, we will not go,” was Aldo’s simple reply. We had always respected an unspoken veto policy for all sailing plans. Sailing can be hard enough when you like the conditions. There’s really no need to head out when you fear them.

So we stopped and we regrouped and eventually we decided to sail to Jamaica, downwind at last, into the heart of the Caribbean Sea and with a world of options open ahead of us. From Jamaica we could head south towards Colombia and Panama or west towards Belize, Guatemala, and Mexico. Jamaica was brilliant.

It was on this sail from Haiti to Jamaica that there was a shift in the qi of my journey. Several new rips started to appear in the genoa, the predictable result of time, UV degradation, and good, hard use. The electronic tiller pilot died in a glorious blaze of flashing lights. Another winch took flight from the side of the mast. The fuel tanks started to decompose at a remarkable pace. The trip transpired without unnecessary risk but not without undue suffering. All of those little things were starting to add up.

In Jamaica I sat aboard the boat secretly mired in a low-grade panic about how to acquire a new tiller pilot and how to safely proceed with what felt like a decaying boat. I had an obligation to be back in Washington DC in October of 2017 for my niece’s wedding, and I had been worried about finding a hurricane hole somewhere in Central America where I could safely and affordably haul out for a month or two of travel. Adding now the challenge of new electronics, possibly new fuel tanks, and a need for new sails just over the horizon, and that trip south or west started to look like an escape tunnel that led to a fire pit. It just didn’t feel right.

“Ollie’s girlfriend put seven tubes of caulk around the chimney on the roof, so we’ll see if that works,” came the words from my friend Eric, who was watching over my leaky old house in the Shenandoah Valley of Virginia. A small rental income from this beautiful old victorian home funded my sailing life aboard Ave del Mar. One of my tenants had just been evicted, so I had been without income for a couple of months, and now work had to happen to fix the roof before the vacant unit could be rented again. The house was just like the boat: lovable, capable, a bit tired, and in real need of attention.

There was a time a couple of years ago not three days into my journey from Annapolis when NOAA weather radio was calling for a small craft advisory on the Chesapeake Bay with sustained south winds over 25 knots and some sizable seas. I elected that day to feel my way into the Piankatank River through a dense fog, where with the help of my radar and AIS I fumbled my way up to an anchorage near Glebe Neck for three days of respite. Despite the fact that I sail solo, despite the fact that I like being alone out on the ocean, I do not embrace unnecessary risk. That’s just how I sail. Risk assessment was all that could go through my head as I sat in the marina in Jamaica staring at nautical charts and trying to make a plan.

Distilled down, my risk assessment looked bleak. At the very least my fuel tanks needed clean-out portholes added and the condition of their interiors assessed. It is possible they needed replacing altogether, which involves removing the cockpit sole and the engine, hardly a weekend project for a shade tree mechanic. The sails were taped where they were decaying, but that was a temporary fix. The autopilot was simply dead and needed replacing. Meanwhile, the rental house appeared to be collapsing under its own weight. South and west were calling, but so was my obligation to return for the wedding. In the end I knew what I had to do. I had no desire to be one of those derelict boats that ends up in some third world backwater, rotting away and blaming bad luck.

Forward is a strange word that means so many different things to so many different people. To me it meant taking steps, good steps, regardless of their geographic direction. Cutting miles up the Piankatank River to hide from stormy weather when I was fully green and inexperienced was forward progress because it was the safe thing to do. Delaying my crossing to the Bahamas from South Florida was forward progress because it was the wise sailing decision. Not beating into those trade winds to try to make the Dominican Republic under a cloak of false pride was forward progress, a pragmatic deferment to weather and sailing conditions.

So Ave del Mar and I are going to point the bow towards Reedville, Virginia, and head back to the marina where our journey began four years ago. I’ll be able to get the house in order, see some friends and family, officiate a pretty special wedding, and, in the quiet comfort of Jennings Boat Yard, I’ll be able to deal with those fuel tanks, winches, sails, and whatever else requires my attention, this time with the invaluable benefit of experience.

In 2013 I left Jennings Boatyard a starry-eyed dreamer. With a little luck, four years later I hope to return a sailor.