“Perfect is the enemy of good” is a loose translation of Voltaire’s “le mieux est l’ennui du bien.” It means maybe calm down a bit with the perfectionism, and it took me decades to learn. It’s hard not to constantly strive because society runs on the notion of “best.” Influencers churn out listicles of the “best” hikes, hotels and chicken carbonara. Pop-up ads peddle the “best” self-care routines, and a good margarita no longer makes the grade. It’s “best” or nothing.
So, whenever someone at a gathering learns I run charters and inevitably asks me about the “best” place to go, panic runs off leash in my brain. I have an aversion to the question itself. “Best” is, by definition, an exercise in hubris. Like the “Persian flaw,” where a mistake is intentionally woven into a rug to embrace humility, it’s better to be precisely imprecise. And as these intrusive and completely off-topic thoughts barrel through my head, I realize the questioner is staring at me, wondering if I’m deaf.
I have no idea what others think is “best” nor do I believe there is a singular answer. Croatia is great for history buffs while the Caribbean is perfect for beach and bar devotees. More importantly, the “best” sailing vacations are oftentimes the ones that didn’t go as planned. A recent charter in Sicily was far from perfect, although I can’t say I wove defects into the trip on purpose. We had no wind to sail, I was off my game on the mandatory Med moorings, and there was strife among the crew who came with their own baggage of anguished romances, harried work demands, and expectations of the “best” vacation ever. Everyone landed on that dock very feelings-forward so “best” was going to be a tall order.
One afternoon we dragged anchor, and another time I realized to my horror that we had dropped the hook with the mainsail still up. I’d have been grateful if Neptune himself had swallowed us up right then. But the previous evening, we sat on deck watching a volcano hurl fire and ash into the night sky like a pyrotechnic Disneyland. The afternoons were spent wandering ancient alleys chock-full of rustic restaurants, consuming designer cocktails in villages so quaint they could have been movie sets. Despite diabolical anchoring gremlins and uncooperative weather gods, we fused together an imperfect but unforgettable visit to an exceptional place.
I think back to other imperfect trips like the punishing Meltemi wind that had us pinned on a dock in Greece or the anchor that got wedged upside down in the roller in Croatia. I’ve sat out anchor watches in a blow in Tahiti and lost the GPS signal in Mexico leaving us to rely on dead reckoning. Florida served up a bloody crime scene cleanup after someone fell and hit their head, and I’ve had to beg to borrow a forklift battery from an island ferry to start our boat engine in the Grenadines. These weren’t perfect trips but not only were they good, they became memorable precisely because they weren’t flawless. They still play starring roles in the frequent retelling of past adventures because imperfections make the best stories.
At some point in my life, I realized that if I didn’t embrace the idea of good over perfect, future me was in for a rough time. I’m not saying you should settle for “good is good enough.” I just find that any time I can kick my feet up and take a breath to appreciate the good, I may be as close to perfection as I need to be.
Of course, by the time I gather these thoughts to answer the inevitable “best” charter question, my interrogator has usually moved on in pursuit of fresh canapés and greener conversation pastures. Oh well, it was good while it lasted.
This article was originally published in the August/September 2026 issue.
