Four years ago, on a Sunday morning in October, a woman sailing for the New York Yacht Club crossed a finish line in northeastern Italy ahead of more than sixteen hundred other boats. She was the first woman ever to win the race, and the first American.
Most people I know in Sarasota have never heard of it. And I'd bet the part they'd find most surprising isn't the sailing. It's who comes to watch.
One start line, every kind of boat
The race is the Barcolana, and it happens today. It is held every year in the Gulf of Trieste on the second Sunday of October, and this is its 58th edition, with the start set for 10:30 on a line between Barcola and Miramare Castle.
It began in 1969 as a season-ending race for the local sailing club, the Società Velica di Barcola e Grignano, with 51 boats. It grew and grew. In 2018 there were 2,689 boats and more than 16,000 sailors on the start line, and Guinness World Records named it the largest sailing race in the world.
What makes it different is the formula. Professional crews on enormous racing yachts start on the same line as families in small cruising boats, sailing the same course. Everybody races. Nobody needs an invitation.
In 2022 the boat that crossed first was Deep Blue, with Wendy Schmidt at the helm, and she took home the prize for the first woman skipper with a mixed crew as well.
The city on the Rive
Here is the part I love. The Barcolana is not only for sailors. The whole of Trieste turns out. People crowd the Rive, the long seafront below Piazza Unità d'Italia, and line the Karst hills above the city, which make the gulf a kind of natural stadium. For ten days there are stands, concerts and a village along the water.
So what does a city wear to watch the biggest race in the world? Not a costume. Trieste is a real port, and its women have no need to prove it with anchors and rope. What you tend to see on the Rive is ordinary city clothes, with the sea let in at one point only. A stripe. A navy jacket. A white bag.
It is also a city that knows wind. Trieste is famous for the bora, a cold wind off the Karst so strong that the town has at times stretched ropes along some sidewalks for people to hold. Nobody there dresses like a sail.
One nautical thing, not five
That is the Trieste rule, and it travels well to our own bay. Nautical dressing goes wrong the moment it becomes a theme: stripes, plus anchors, plus a captain's hat, plus red, white and blue all at once. It goes right when there is exactly one maritime idea and everything around it belongs on a city street.
The striped dress in these photos is the simplest version I know. It is a shirt dress in 100% lyocell, made in Italy, with a bow at the neck and a ruffle at the hem, and the stripes change direction at the drop waist so the dress moves. Add sunglasses, a structured white bag and a sandal, and stop there. It reads like a woman who lives near the water, not one dressed up as a sailor.
When the air turns, the Trieste answer is a jacket with a tailored cut rather than a windbreaker. A cropped black-and-white jacket with its matching shorts works as a set on a warm afternoon, and the jacket alone goes over the dress at night. We wrote more about splitting pairs like that in how to style a matching set.
So this Sunday, somewhere near the water, try it the Trieste way. One stripe, one good bag, and a city pair of shoes. Then watch the boats. The sets are in the sets.
She travels to Italy each season to hand-select the boutique's collection.
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