Just past the new year, about boat show time, I make a list of the boat stuff that needs replacement.

One of the items I check is my boat shoes. It’s the condition of the sole that draws my attention, especially after a worn sole sent me head over heels off a wet swim platform, dumping a case of Sam Adams, my favorite sunglasses and myself into the cold Everett harbor a couple of years ago.

Back in 1970, my sailing mentor cautioned me about the type of boat shoe I should wear. Joe stressed that not all the rubber soles were good on a deck, then he paused and said, “Most of the brands made can’t hold a candle to the Italian boat shoes I once had.” His eyes now half closed, his voice softened as he relived a sweet memory. “They had a rope sole—you know, real hemp rope—and they were soft and pliable on your feet and worked so well on the deck. I had a pair of them when I was sailing in the races at the academy in ’26. Of course, they rotted away years ago, but man, they were nice.”

Four years went by and my boat shoes were in need of replacement. However, in Puerto Rico, where I was living, there wasn’t a great selection of boat shoes from which to choose. The locals had small feet and I don’t; it came down to just one ugly pair available in San Juan. Surprisingly, the next Friday my wife came home from work to say she had won a free pass for two on Air France and we could now have that honeymoon in Paris and Rome we’d always wanted.

I was stunned. Rome, you say? You mean Italian-boat-shoe-Rome, where there was an outstanding dollar to lira exchange rate to boot (no pun intended)? The news was heaven-sent—or so I thought.

Three weeks later, the 727 touched down in Rome and I couldn’t wait to get the required sightseeing out of the way and start shopping. On the morning of the fifth day, we started looking in the windows of the shoe shops. I was elated when we discovered a small chandlery that catered to the well-dressed nautical crowd. Centered in the window display was a pair of Italian rope-soled boat shoes. The interplay of cream canvas with soft leather piping indicated that their look and quality was unmatched, but so too was their price. However, like a snake transfixed by the flute of a charmer, I stepped inside.

The salesman, in his delightful English, bore in for the sale. “My brother heesa live in Ceeecero en Chicago, you know Ceeecero?” Quick to find my size, he assured me these were finest Mediterranean boating shoes made, and what’s more, “They looka so nice, yes?” I had to admit he was correct. He explained the special care of the soles and the break-in method that must be followed. “Yousa should no wear more than two hours a day,” he cautioned, “notta too much on the strada. Yes?” Excited, I decided to wear the new shoes back to the hotel, just two blocks away. However, upon exiting the store, my wife noticed a little dress shop just down the street—and then another, and another.

Four hours later, darkness found us miles from the hotel and my dogs were barking with each painful step. Overbalanced with packages in both arms and my feet screaming at every step on the cobbles, I hobbled and weaved like an old man. Frantically we searched about for a taxi, but it was the dinner hour and none were to be found. Then, while leaning against the rim of a large fountain, we spied a horse and buggy plodding ever so slowly into view.

It was a large gray horse pulling a weary open trap, one of the many that give long evening rides around the streets and lighted monuments of Rome. Inching toward us and back-lighted by the headlights of the cars, it was to me a vision akin to that seen by the survivors of the Titanic when the first rescue ship drew close. Waving our arms soon attracted the driver’s attention and he pulled up to a stop. Intently, from behind large bushy eyebrows and a very full mustache, he cautiously studied us, a cigarette hung loosely from his lower lip.

The driver could speak no English and I no Italian; my wife spoke Spanish as a first language and had taken some high school Italian—or was it Latin?—years before. A few short sentences of fractured Italian on our part, reflected by confused glances of the trap driver, then a pantomime followed by more fractured Italian, followed by more head-scratching by the driver. Subsequently, after some expressive waving of arms and more miscommunication, we finally understood that the driver was also on his way home for supper and didn’t want to take us back to the hotel. However, my wife does not accept no easily.

She continued to cajole the poor man while I—he without a bit of linguistic ability—walked close to the horse to pat its shoulders. Negotiations became hotter with each give and take, and the decibel level rose by a factor of 10. Attempting to stay out of the crossfire, I walked toward the horse’s rump to get a closer look at the buggy’s harness. Out of habit, I patted the old horse on its derriere and then, as if a secret signal had sounded, the horse’s tail shot straight up and it relieved itself on me. Boy, did it relieve itself.

Almost cemented in place, I looked down to see my new Italian rope-soled shoes buried beneath a large pile of steaming green horse pucky. The trap driver exploded in a hail of Italian—I think directed at his horse—then broke out in laughter that sounded more like a braying jackass. Struggling to free myself from the green mess, I slipped on the cobblestones and fell to the ground, scattering the packages and ripping my slacks. Much to my frustration, my dear wife joined the old man in gales of laughter while I struggled to my feet and, walking like a duck to the fountain, attempted to wash the worst of the mess from me and my brand new shoes.

After a couple of rinsings, it appeared my slacks would clean up enough to get me back to the hotel, but the canvas tops of the shoes were ruined and the soles had soaked up the horse’s present like a sponge. As I changed back into my old shoes and gathered up the packages, the horse and buggy drove off, the driver still shaking in laughter.

We were unable to find a cab and considering the distance to the hotel, I unceremoniously tossed the once handsome boat shoes into the still steaming green mess by the curb and began the long, painful trudge back to the hotel and clean clothes.

That was then. Now I buy my boat shoes on sale, or at the boat show. Nothing fancy, just as long as they are comfortable and have a good, sticky sole. When it comes to horses and buggies—like those you see in Victoria around the Parliament buildings—I cross over to the other side of the street and keep my hands to myself.

Mike Oswald is a boater and retired airline pilot who lives in Tulalip, Wash. and now buys his boat shoes in the U.S.