Chances are that if you’ve visited Venice during Carnival, sunbathed on Croatia’s beaches, or skied on Austria’s slopes, the nearby city of Trieste did not appear on your itinerary.

That sums up the troubles that this beautiful Italian port town has had since 1918. Before then, Trieste was a vital hub of the Austro-Hungarian Empire. It was a place where archdukes built castles; where Italians, Slavs, Germans, Jews, and Greeks came to strike it rich; and where some of the world’s greatest writers penned their masterpieces.

Karl Marx wrote on the city’s ascendancy in the New York Daily Tribune in 1857: “How therefore did it happen that Trieste and not Venice became the point of departure for the flourishing new Adriatic navigation? Venice was a city of memories; Trieste on the other hand like the United States had the advantage of not having any past.”

Today, however, Trieste ambles into the new millennium like an elderly Austrian aristocrat: Elegant, eccentric, and irrelevant. A series of geopolitical mishaps have deprived Trieste of its economic fortune, and consequently, of its population. The city’s approximately 210,000 inhabitants are among the oldest in the world: For every birth in Trieste, there are three deaths. The census count is smaller today than it was in 1914.

Trieste’s city leaders had hoped to reverse the trend last week. Trieste was one of the three finalists to host the 2008 International Exposition, an event that brings scads of visitors, publicity, and public and private investment. But the judges at the Paris-based Bureau International des Expositions narrowly chose Zaragoza in Spain instead.

Even though Trieste fell just short in Paris, it should still make the cut in your future European travel plans. The city’s nuanced cultural layers make it one of the most intriguing places on the continent. As writer Scipio Slataper once noted: “Everything in Trieste is double or triple.”

It all starts with geography. If you sit on a bench in Piazza Unita in the heart of town and look across the bay, you’ll see the Italian coastline to the west, the mountainous nation of Slovenia to the east, and the tip of sunny Croatia to the south. Although Trieste is in Italy – barely – the white, stately buildings in the central square look Austrian. That’s because they were built under Hapsburg rule centuries ago.

As its central European holdings began expanding rapidly in the 1700s, the Viennese royal family – which traced its origins to mountainous Switzerland – deemed it necessary to build a port for maritime trade. The closest option was Trieste, which at the time was an ancient but tiny fishing village.

To attract merchants, the Hapsburgs made Trieste a free port, waiving all trade levies, and allowed freedom of religion. The incentives beckoned ambitious merchants from throughout the Austrian empire and beyond. In a few decades, these merchants created a port that was among the busiest in Europe, and a city that represented their varied backgrounds. Because of the city’s long history of religious pluralism, Trieste is the only Italian skyline dominated by the tops of churches that aren’t Catholic – the spire of the Protestant church competes with the domes of the Greek and Serb Orthodox churches, which in turn compete with one of the largest synagogues in the country.

Trieste’s menus are equally diverse. Traditional Italian peasant fare like polenta appears alongside speck, a smoked Austrian version of prosciutto, as well as Venetian sardines, called “savor,” and civapcici, Slavic spicy meatballs.

And don’t forget the coffee. Thanks to its Austrian heritage, Trieste has perhaps the finest cafes, per capita, in all of Italy, and its coffee culture is among the most refined in the world. No wonder, then, that one of the world’s preeminent coffee producers, Illy, is based in the industrial part of town. Starbucks hasn’t dared to open its doors in Trieste.

Other foreigners, however, have left their mark. Archduke Maximilian, the younger brother of Austrian emperor Franz Joseph, built his striking, bone-white Miramar castle on the water on the outskirts of town in the 1860s. He left just after it was completed to become emperor of Mexico. He should have stayed home: The archduke was murdered by Mexican rebels three years after his departure.

James Joyce lived in Trieste on and off from 1904 to 1920, teaching English to wealthy Triestines. It was there that his children were born, that he wrote “A Portrait of the Artist as a Young Man,” and that he started “Ulysses.” German poet Rainer Maria Rilke was inspired by the area’s natural beauty. He wrote the “Duino Elegies” while vacationing on the white cliffs that abut the sea just outside of town.

Trieste’s fall from grace began after World War I, when victorious Italy annexed the city from Austria. While Trieste’s port held a special status in the Austrian empire, it lost its advantage in peninsular Italy, which already had Genoa, Naples, and Venice. Mussolini’s heavy-handed Italian nationalism subsequently created ethnic tension in the historically heterogeneous city. That tension bubbled into racial violence between the Italian and Slavic populations at the end of World War II. Even though the town ended up on the right side of the Iron Curtain during the Cold War, Trieste was never able to regain its former glory.

Despite this, Trieste’s beauty has persevered. The Austrian square, with its buildings that look like a row of wedding cakes, remains a stunning place to watch the sun set. The flowers at Maximilian’s castle still perfume the coast. And the city’s streets continue to stir wonder. “I would like to get back to Trieste,” Joyce wrote to his brother in 1907, “because I remember some nights walking along the streets in the summer and thinking over some of the phrases in my stories.”