Ever notice how sea stories just get better with the passage of time? The more years that disappear in the wake and the more times a tale is told, the better, funnier, and more heroic each becomes. In my circle of sailors, we have a treasure trove of seasoned anecdotes with an ever-rising humor quotient. They serve as individual bright spots of sailing memories that are rehashed whenever we gather. Here, the names have been (mostly) changed to protect the (seriously) guilty.
As we motored to our next Greek island, Frank and I were sitting at the helm deep in conversation about AIS and general safety monitoring tools. We held forth our strong and somewhat snotty opinions about the importance of a good lookout when we hit a thin, uncharted, six-foot marker in the middle of nowhere. Luckily, it bobbed back up after it passed between the hulls of our chartered catamaran with no harm done. A few moments of silence followed. You could almost hear the crickets chirping.
On another trip, also in the Mediterranean and also with Frank, we executed a quick and efficient drop of the hook noting with some self-satisfaction how our anchorage neighbors looked over at us in what we deemed was admiration. It was only then that we realized we had left the mainsail hoisted during the maneuver. The damned Bimini obscured our sightlines upward, which is an excuse we’re sticking with.
One exceptionally fierce night, I sat out an anchor watch with winds building from midnight on. I had come up on deck in my white bathrobe to find chaos in the anchorage and although we were sitting still, boats around us were dragging anchor and coming close. Riding out the lumpy conditions, we fought chafe on our anchor line for hours. Then, with a boat bearing down on us, I could take it no more and ran to the foredeck, yelling into the shrieking wind to get the skipper’s attention. I was later described as a giant white bird with flapping wings jumping and hollering on the foredeck like a thing possessed. I can’t get anyone to shake that visual.
On a training vessel run, we had a particularly vexing lady, let’s call her Janet. We ran for seven days straight teaching seamanship, navigation, watch-standing and steering by the compass, and we never once during that week anchored or arrived in port. Every morning, Janet would materialize in the galley and ask if there was any milk. Maybe she thought we had sailed by a 7/11 in the dead of night but each morning, it was a surprise to her that we still had no milk. Janet refused to stand her watch stating that she would only steer if we were under sail. Since we had little wind, we mostly ran under power, and Janet never touched the wheel. In true sea lore form, she went from unpopular to immortalized in just a few iterations of the story.
Another time on a delivery coming up the coast from Baja, we were caught in a freak storm that produced 15-foot head seas and gusts to 50 knots. These were conditions that we had never seen before or since on this stretch of water. As we wrestled with headsail changes (no furler here), we bounced around the foredeck straining our harness tethers, but all was copacetic with the crew. Other than frozen fingers, we were fine. Over the VHF radio, we heard a call about a boat that was “in trouble” just offshore and as we scanned the horizon we realized they were referring to us. We were indignant even as we sailed into the shelter of a small harbor. There, we were met by a crowd on the jetty cheering our dramatic arrival and melting our ire. The story got less irritating and more heroic each time we shared it, which was often.
Other than fine wine and hard cheese, there are few things that get better with time—just ask my knees. Tall tales of the cockpit age with great drama and the occasional embellishment, and with time the freakouts, screwups, onerous crew, grim weather, freezing watches under the dodger, and truly dumb decisions mellow like a smoky scotch. These stories may not be why I go out there, but they do give me another reason to go back because I can never have enough silly sea stories.
This article was originally published in the April 2026 issue.
