I arrived at the marina with two simple tasks. Neither of them to sail.

The plastic stoppers that keep that the car from running off the end of our traveler both disintegrated, and (possibly for years) I’ve been limiting the range of the traveler with knots in the control line. I finally got around to fabricating replacements out of small scraps of starboard left over from my compass installation and intended to install them, which I expected would be trivial. I also hoped to replace the clam cleats that are theoretically supposed to secure the traveler control lines with normal cam cleats, which I expected to be obnoxious because I can’t tell how they’re secured on the inside of the coaming—at least one spans a bulkhead and there’s something over the nut on the aft portion that I can’t identify by touch or see from any vantage, even when hiding in the lazarette. I brought my budget endoscope to try to figure it out, which is never a good omen.

As I was dragging my tools out into the cockpit, I saw Rest Less returning from the bay. The skipper was singlehanded, so I jumped off the boat and ran down to his slip to help him dock. He came in without much issue, I handed him some lines, and we exchanged brief pleasantries and weather reports.

In the short walk back to my slip—not more than 100ft—I had about a million thoughts. Why wasn’t I wasn’t out there singlehanding? When am I going to get weather like this? Light wind, even less in here at the marina, easy to dock…people sail singlehanded all the time, right? They can’t all be radically better sailors than me at this point. Children have sailed around the world. The little voice in my head was still going as I found myself putting the tools away and prepping the main.

Getting in and out of the dock was my biggest concern. I cast off all of the dock lines except for the spring line, which I very carefully positioned on the piling so that I’d be able to easily grab it when I got back. In the process, I’d warped the boat a third of the way out of the slip, so I was just about clear before even engaging the engine, and with no wind or current to speak of things went surprisingly well. By the time I was at the end of the creek, I had the main up, then I unfurled the jib, shut down the engine, and was just sailing.

This wasn’t entirely new. I’ve singlehanded before (I’ve just always previously had Jen on shore to help me dock once I returned), although this time, I did have some unexpected problems.


I’d set up the autopilot to allow myself more hands to handle the lines, but for some reason, ours has never really worked that well in the bay, where we’re frequently close hauled, tacking a lot, dealing with wakes and messier wind, etc. In this case, it also kept slipping off of the tiller nib, usually at the most inopportune times, and I kept getting caught in irons or inadvertently backwinding the jib, often to the point where I just had to tack to keep going.

I eventually gave up on the tiller pilot and sailed north, manually, on a leisurely broad reach to regain some composure. With the tiller in hand, I was able to sail normally, and ran down a beautiful Hinckley Bermuda 40 (I think) that was inexplicably sailing jib and jigger in very light wind. I got close enough to confirm the Hinckely logo on the cove stripe, with enough speed that I could have easily adapted my Wall of Shame stamp for the Catalina 27, but ultimately tacked away in gentlemanly fashion and headed upwind toward marker BB. Even when beating to windward, I had an easier time steering with my foot through tacks than using the autopilot.


When I decided to call it quits and take down the mainsail, I found that I’d gotten an override on the halyard winch. With the sail at full hoist there was no play in the working end of the line to get the override out. I tried to free some portion of it with a screwdriver, and when that didn’t work I tried wrapping the standing end once backward around the winch and using another winch to pull it free, but it wouldn’t budge…and I somehow managed to get an override on that winch too. I have no idea.

The wind had picked up a bit at that point, and I didn’t want to try docking alone for the first time with the sail flying, so I chalked it up as a $100 mistake and cut the line. It was not my finest hour. At least my knife worked. In my stricken state, I also couldn’t remember how to tie a sheet bend, and didn’t have the time or inclination to look it up while standing on the cabin top with no one at the helm, so I tied the two halyard halves together with a square knot and locked the bitter ends with a dozen or so half hitches, hoping that the halyard would stay intact long enough for me to re-run a new one without having to go to the top of the mast.

When I did get back to the dock, the crew of Elenora were there to assist, my spring line worked as I imagined it would, and things went generally smoothly.

Next time I try to do this, I should probably be a little more intentional about it. I hadn’t even planned to sail, and hadn’t brought the usual sailing accouterments. I did technically pull off sailing alone though, despite having to return the next day to replace the halyard (at which point I also completed approximately half of the original maintenance that I intended to address). A marginally successful day of sailing is still a lot more entertaining than most completely successful days spent on land though, and sometimes I think it’s good for my sanity to relent to the voices in my head.




"Prepare to fend off the bridge abutment."