TRIESTE, Italy — The Bora wind blows so fiercely through Trieste, a melancholic port town on the Adriatic Sea, that some sidewalks are lined with handrails. The wind maddens pedestrians, but it also fills the sails of skippers who come from all over to compete in Italy’s aquatic equivalent of the New York City Marathon.
Before this year’s race, the sleepy docks that once served as the main port of the Austro-Hungarian Empire buzzed with life. Olympic sailing crews, boating enthusiasts and excitement-thirsty locals packed Trieste’s piers, old world cafes and vast square facing the sea.
Everything was in place.
Except the wind.
“Not a breath of it,” Pietro Faraguna, 36, said before dawn on race day as he and members of his crew collected their boat in a neighboring town.
Last year, the 50th anniversary of the Barcolana, as the race is called, included 2,689 boats with 16,000 sailors, making it the largest regatta in the world by some counts. Mr. Faraguna and his friends finished in 15th-to-last place.
This year he was not sure whether to try for a better finish or compete for a newly introduced last-place trophy or “give up if it’s going nowhere.”
For now, Mr. Faraguna and his crew just needed to get into position at the starting line. In the calm morning air, they loaded up their secondhand boat, the Confinandante, with supplies of wine and beer, and motored toward the race’s starting line.
As one of the crew put bottles of friulano, prosecco and sauvignon in the fridge, the decades-old boat puttered past mussel farms and the Duino Castle, a 14-century fort overlooking the Gulf of Trieste.
Mr. Faraguna, an amiable father of two and constitutional law professor, reflected on his previous 12 Barcolanas. He talked about how the thermodynamic differences caused by the shape of the coast altered wind conditions and how the Bora — named for Boreas, the Greek god of the north wind — howled down from the Julian Alps to the sea.
“But this isn’t going to happen,” Mr. Faraguna said, observing that the dark, flat water looked as motionless as an oil spill.
On the other side of the boat, Giacomo Longo, 32, received a picture from a friend already chugging a white wine spritz near the starting line. Mr. Longo checked his nautical watch and reported a meager high of 4.35 knots of wind. The crew shrugged and decided to unfurl the white-and-blue-striped sail. Some stink bugs fell from it onto the deck.
A couple hours later, the Confinandante reached a harbor near the Barcolana’s starting line and just behind the Miramare Castle, built by Archduke Ferdinand Maximilian, who, tradition holds, was forced to dock at this spot in 1855 by strong gusts of the Bora.
Friends of Mr. Faraguna climbed aboard, carrying more refreshments and a guitar. One of the men’s wives, Giada Dal Mas, 36, told the crew that “since there is no wind, at least try and catch some sea bass for tonight.”
The Barcolana began in 1969, when a few friends at a local sailing club organized a race with 51 boats. Since then, the winds have come and gone as the skippers race from Miramare Castle toward Slovenia and back to the finish line near Trieste’s Unity of Italy square.
Some years, the Bora has been so vicious as to break masts. Others it has been so nonexistent that boats drifted back to Trieste backward.
Over the years, the race has grown into a major enterprise. Last year, the 50th anniversary brought about 70 million euros into Trieste. Its corporate sponsor, Generali, the insurance giant founded in Trieste during the port’s glory days, slaps its name everywhere, from the race bibs on the boats to the red inflatable buoy marking the finish line.
In the days before the race, the dock in front of Trieste’s main square turns into a nautical Times Square, with beer, sausage and Barcolana merchandise vendors dwarfed by the sails of megayachts advertising luxury cars (“Sail With Land Rover”), banks, fashion brands and prosecco.
But the spirit of the race, said the Barcolana’s president, Mitja Gialuz, a 44-year-old law professor and former sailing world champion, was better captured by the hundreds of smaller sloops, ketches and traditional wooden passera fishing boats that competed, or got completely sloshed, in the big boats’ wake.
He noted how last year’s official regatta poster featured the celebrated artist Marina Abramovic declaring, amid a national crackdown on migrants, “We’re all in the same boat.” Local officials in the anti-migrant League party were furious, but Mr. Gialuz said it was just the right, inclusive message for a faded cosmopolitan city looking to shed its provincialism and make a global comeback.
“Once we became the biggest race in the world,” he said in front of a boat-sized sardine sculpture made from recycled Trieste plastic, part of the race’s expanded environmental consciousness, “we assumed a bigger responsibility.”
Still, most of this year’s participants focused mostly on the task at hand — getting their sail boats to go anywhere.
On the eve of the race, a room of skippers listened to organizers wish them “fair winds” but also remind them that “since there are very, very light winds in the forecast,” judges will be especially watchful of boats that used their engines at the opening bell.
Just before 10:30 a.m., Mr. Faraguna’s boat inched forward to the starting line of white sails, which from a distance resembled a long mountain range of snow-capped peaks. Surrounded by boats named Lady Killer, Passion Fruit and Stairway to Heaven, Mr. Faraguna waited, ready to race.
The starting cannon fired. The smoke cleared. Nothing changed.
Eventually, some of the professional crews sailing state-of-the-art ships captured enough puffs of air to move forward. The race’s organizers decided two legs of the race was enough and canceled the last two.
The Way of Life, an early favorite, won with a time of one hour, 54 minutes and 10 seconds. Mr. Faraguna’s boat hardly moved at all.
For the next few hours, Mr. Faraguna and his friends drank white wine and Union Svetlo beer and sang old Trieste folk songs about how life was better under the old empire (“We weren’t lacking pasta and chickpeas.”) They went swimming.
Early in the afternoon, with no wind in sight, they called it quits and motored back to the pier, where they happily basked in the applause directed at Way of Life, which finished another victory lap behind them.
Mr. Faraguna went home to see his wife and take a nap. As he slept, some of the last boats sprinted, or inched, to the finish line.
“Five, four, three, two, one” the crew members of Itaparica shouted with relief as they finished in 948th place. It was just shy of 5 p.m., nearly seven hours after the start. A few minutes later, the Cassiopeia II crossed and one of its passengers screamed wildly into the no wind.
Dario Motz, an official from the Italian Sailing Federation, stood on the elevated deck of a vessel recording the finish times. He looked at the ships lingering in the distance and debated with his colleagues whether they had frozen purposefully in pursuit of the loser’s cup.
“It’s a fight for last,” he said.
At 6 p.m., as Mr. Faraguna woke to play with his young children, the Xeinos, a 50-foot yacht sailed by Serbian, Montenegrin and Italian dentists, took the last-place trophy with 1,098th place.
Mr. Gialuz, the Barcolana’s president, was there to climb aboard and celebrate. This was the spirit, he said, that would reinvigorate his town.
“For a long time, Trieste was like a dark and stuffy room,” he said. “The Barcolana opens up the windows. It lets the fresh wind in.”