
It was half past midnight and the wind had been building for the last few hours. We had left the west coast of Puerto Rico the previous morning, sailing off anchor and through the cut, and now were blasting towards the Turks and Caicos. It had been a slow start out of Puerto Real. The mountains of Puerto Rico reach 4,390 feet, and we felt the wind shadow even 20 nautical miles out.
Fully exposed now to the trade winds, we were also experiencing the forecast system that carried a stronger breeze and bands of heavy rain. The coast of the Dominican Republic lay 15 nautical miles to port, but there was no chance of seeing any light from the island in this weather.
It was just my father and me on board Ben-Varrey, my 1969 Luders 33. He had joined me in Saint Thomas after I singlehanded from Sint Maarten. We would be tackling about 1,000 nautical miles, sailing up through the Exumas, an amazing opportunity to spend time together.
Despite the weather conditions, we were enjoying what was to be a three-day passage. Ben-Varrey was sailing fast–touching up to 14 knots of speed over ground as we surfed down the long-period waves and holding at least 8 knots otherwise. Not bad for a 53-year-old boat, even if we did have some current to thank. Jack, the windvane autopilot, held a steady course, with plenty of apparent wind from nearly dead astern. The motion was soft, with little roll, and just a subtle heave as we worked our way through each wave. We were able to duck out of the rain most of the time, just keeping an eye to the horizon, as the boat sailed herself northwest.

None of this control or comfort was an accident. Before the breeze built, we had already swapped headsails from a 130% genoa to the 90% jib—a more suitable headsail for the 28-35 knots of breeze we expected on a downwind course. We also tucked a reef into the main, followed shortly by a second. While this removed some power that we wouldn’t need, it also balanced out the boat nicely for the autopilot. We were set wing-on-wing, with a preventer locking the boom in place.
Managing sails is at the core of shorthanded sailing, especially offshore, and headsail changes happen regularly on Ben-Varrey. Each boat is different, of course, requiring different strategies, and on Ben-Varrey we’ve made some choices some might consider old school, but I find them to be fundamental to safe, comfortable shorthanded sailing.
Forward of the mast, we choose between a storm jib, staysail, 90% jib, 130% genoa, drifter, and an asymmetrical spinnaker. Most significantly, the headstay and inner forestay are set up for hank-on sails. This simplicity ensures sails always come down when they should and are contained on deck when they do.
A majority of sailors probably rely on furlers, and this gear surely has vastly improved on the reliability front. But they often leave me in a conundrum of whether I attempt a messy headsail change, since the luff is free to blow overboard as soon as it comes out of the track, or deal with the awful shape of a partially furled sail. A cutter rig gets a step closer to ease of handling but still can’t carry a full range of headsails on only two furlers. Also, the extra windage of a furled sail hurts air flow over the working sail and the drag is far from ideal in a real blow. A lack of diligence can lead to a furling line chafing through or getting jammed, which then requires fast problem solving to avoid another layer of problems, especially if maneuvering in close quarters or if exposed to heavy weather.
Every approach carries compromise. Hank-on sails are intermittently more work, but if the sail sizes are manageable, I would always opt for hanks.
Regardless of your choice, changing sails shorthanded is a reality with every setup at some point in time, and the ability to do it efficiently and safely is worth practicing. The real challenges with headsails are making sure nothing washes overboard, and folding up the old sail. Tackling a headsail change with two people is nice, but that isn’t an option when singlehanding, and when doublehanding I prefer to let the off-watch rest. So, here is my approach to confronting it alone.
I always keep sails secured to the boat by at least one corner (typically the tack) so they can’t be entirely blown or washed overboard. In anything but very calm weather, I leave the new sail in the cockpit—any time perceived lost in going bareheaded longer is recovered by not juggling two sails on the foredeck. Getting the old sail down to near or below the level of the lifelines will keep it contained, and not letting the new one above that height until hoisting will help prevent it from setting early. Extra sail ties are a great help on the foredeck to contribute to this mission.

Once you’ve dropped your old sail, the challenge is folding. There never seems to be enough room to fold sails easily, but folding keeps the boat organized and makes future sail changes easier. Shorthanded sail changes will result in less than perfect folds, but practice and good technique will go a long way in keeping them reasonable. (In bad weather, it’s not worth trying to fold sails on deck. Stuff them down the hatch and deal with it when conditions improve.)
To fold, I first ensure there are no twists in the sail, and then begin flaking one end and then the other, typically putting in two flakes before moving back to the other side. This takes time and occasional adjustments in the middle of the sail. I keep a close eye on footing while moving back and forth, as the sail is slippery. If the wind is causing any issues, I set a few weights as needed (think coiled halyard tails or anything nearby that has some mass and is still secured to the boat). Once the sail is flaked, it’s business as usual with getting it bricked, secured, and bagged. This takes some practice and always plenty of patience.
When it comes to the main, shaking out an unnecessary reef in more docile weather is exponentially easier than trying to tuck one in as the wind surpasses expectations. With just one or two of us, we don’t have the weight to hold the boat down and there aren’t many hands to do it quickly. So, in addition to having a system in place for swapping headsails, reefing the mainsail needs to be a clean operation.
I believe in simplicity here too. On Ben-Varrey we use slab reefing with all controls at the mast base. To reef, I ease the mainsheet and vang. Then I lower the halyard to below the desired reef point while the topping lift takes the load of the boom. The reefing line is tensioned and cleated, followed by securing the reefing pennant through the new tack point. Halyard tension goes back on, and then the sheet (and vang) can be trimmed. Our main has a hollow leach and no battens, which allows reefing at any point of sail possible. When heading well off the wind, sheeting in the boom part way makes reefing (and shaking one out) easier and reduces wear on the sail. All of this can be accomplished alone, with the autopilot acting as a second crew.

I’ve seen in-mast furling jam too many times to consider using it. Alternatively, in-boom furling has come a long way in the last decade, and while there are a few well-built systems, the added complexity doesn’t appeal to me as a shorthanded sailor. I don’t mind a little extra work each time if it means I avoid something that could put the boat at risk and can’t easily be repaired at sea.
Shorthanded sailing requires thinking ahead—at least one step, and better three or four. Without a full crew on deck, everything happens at a different cadence, one that is eased to a rate that matches the rhythm of the ocean. “Slow is smooth and smooth is fast” is a mantra once shared with me by a USCG rescue pilot. It applies just as much to our shorthanded work as it does theirs. Controlled and intentional sequences keep everyone safely aboard and avoid twisted sheets, broken hardware, and torn sails. Even if I’ve performed a maneuver thousands of times, I’ll visualize the moves before I take any action.
Technology is not the requirement for safe shorthanded sailing. It is the right mindset, the layout of lines and hardware, location of handholds, and systems in place to properly contain and move sails when they are not set. The best way to set up a boat for shorthanded sailing is to go sailing. It’s not even necessary to perform maneuvers like spinnaker sets immediately, just go through the motions. The problems will become evident rather quickly, and then it’s just a matter of making changes and practicing.
Puerto Rico was now well behind us as we approached the shallow waters south of Providenciales, the most populated island of the Turks and Caicos. The wind had returned to the steady trades. With coral heads and sand bars to dodge, we hove-to in the deeper water, waiting for sun to rise and reach a height that would let us visually navigate the bank. Our patience was rewarded by an early morning visit from a curious customs boat that suspected we were up to other business. They opened the side door of their aluminum high-powered vessel to communicate, only to be greeted by a wall of flying water from an excited ocean. With this, and no-follow up by radio, they retreated to shore and we were left in peace again to rest and plan for the last dozen miles of our passage.
SAIL Technical Editor Adam Cove is a marine consultant, naval architect, and former CEO of Edson Marine. He repowered his 1969 Luders 33, Ben-Varrey, with electric propulsion and sails the U.S. East Coast and offshore to points south and east. Follow his travels at covesailing.com.

March 2024