BLENDING INTO THE smoky stone edifice of Caffè Stella Polare, a tiny plaque, barely 3 inches across, announces that this is a caffè filosofico, a salon of sorts for philosophical debate. Next to it, another sign marks the popular lunch spot as a stop on the literary “Italo Svevo Itinerary,” for devotees of that titan of Italian modernism. Sharing the wall, a portrait of James Joyce is accompanied by a quote from the writer: “I came here habitually.”

Italy is justly famous for its visual splendor: gilded angels, riotously bright frescoes, sunrise-colored facades. But in Trieste, a port city of latticed alleyways and hushed boulevards just a 20-minute drive from the Slovene border, words feature more prominently than art.

In Trieste, Svevo wrote “Zeno’s Conscience,” his best-known novel, which was published in 1923. His statue stands at the edge of the Medieval old town, in a piazza that is filled most weekends with antique dealers. Joyce, who lived in Trieste for close to a decade and wrote most of “Dubliners” and all of “Portrait of the Artist as a Young Man” there, also gets a statue, on a narrow bridge crossing the city’s Grand Canal. Sir Richard Francis Burton and Jan Morris are among other noted writers who have felt the city’s pull.

Trieste has been called the ultimate nowhere-place: officially part of several successive countries and empires through the ages, yet spiritually bound to none of them. Many of the 200,000 Triestine, I came to learn, do not see themselves as truly Italian. They belong to Trieste, and Trieste alone. In fact, a small but committed independence movement is seeking the recognition of Trieste as a free city-state.

A Habsburg city under the Austro-Hungarian Empire from 1509 to 1919, Trieste was for a time a city-state and has only formally been part of Italy since its annexation in 1954. It is culturally indebted to the Balkans, to the Venetians, to the Austrians, the Greeks and the Jews, all of whom thrived here. Trieste is so close to Slovenia that my hotel’s tourist map advertised restaurants not just in Italy, but also “just across the border.”

Walking through the compact center of the city, the wind blowing in so wildly off the Adriatic that two old women on the piazza had to brace their canes between the cobblestones, I surveyed a place in which epochs melted into one another like colors on a spectrum: from mosaic-ornamented Renaissance churches to fin-de-siècle art nouveau archways to the midcentury brutalism of bleak suburban apartment blocks.

On the broad Piazza dell’Unità, three sides of the square were lined with grand, wedding-cake-style facades built by Empress Maria-Theresa during the Habsburg empire. The fourth side was empty, with a view straight to the sea.

A barista at Caffè Tommaseo, which is among the city’s oldest. Photo: Christina Anzenberger-Fink & Toni Anzenberger/Redux

From my table beneath the heavy burgundy awnings of the 19th-century Caffè degli Specchi, I enjoyed both the sunset and the tuna carpaccio—fresh from the Adriatic—followed by a Viennese coffee that nearly buckled under the weight of its cream. I finished with the ubiquitous hugo: a cocktail of Tyrolean elderflower, Italian prosecco, mint and lime whose name may or may not reference the Triestine pronunciation of Yugoslavia.

One afternoon, on the hill of San Giusto, where the stately imperial buildings give way to medieval cobblestoned sprawl and ivy-covered houses, I came upon a group of young Serbian Orthodox priests. They were standing beneath a dilapidated Roman stone arch named for Richard the Lionheart, who, according to another legend, was imprisoned here on his way home from the Crusades. I followed them into the compact San Giusto Cathedral, whose gilded mosaics are a clue to the city’s Byzantine influences.

Once inside, they each lit a candle and prayed before beginning to sing. Their voices, at the same time distinct and hauntingly one, echoed off the marble, the Baroque frescoes, the mosaics, each redoubling the sound.

Most of the Vienna-style cafes I visited were cathedral-quiet when I visited: hushed and formal in a way that seemed so alien in the country of the countertop espresso and the typically raucous bar. Men and women, most of them elderly, sat contemplatively over coffees they rarely touched. This was not the Italy of sprezzatura, of gleeful chaos. Everything was muted, languid, precise.

CAFFÈ SOCIETY | Founded in 1914, Caffè San Marco is a Jugendstil classic. Photo: FABRIZIO GIRALDI/Redux

At Caffè San Marco—now in its 101st year—this atmosphere was at once cloying and intoxicating. I sat under Jugendstil molding of copper leaves and faded frescoes of harlequins, pretending that I was not spying on my neighbors. In a back corner, two women were holding a formal philosophical-literary salon, inviting speakers—both Italian and English—to give discourses on the problem of collective versus individual guilt. They spoke slowly, impeccably, in both languages. It was, I thought, the first time I’d ever witnessed a social gathering in Italy where nobody was interrupting anybody else.

The great cliché about Trieste is that it is melancholy: its quiet colors, its cultural indeterminacy, its literary legacies all lending themselves to a certain (to use Joyce’s famous pun) tristesse. But in my week there, I found less sadness than a bittersweet nostalgia for a half-imagined, half-remembered past.

In the village of Duino—a thirty-minute drive north of the city center—I visited the 14th-century castle, still occupied by the local principessa and her family, though the majority of the estate is a museum.

On a cliff top high above the crashing Adriatic, I wandered through room after room of splendor so lovingly preserved it was easy to imagine I might at any moment run into the German Romantic poet Rainer Maria Rilke, who wrote his famous “Duino Elegies” there.

Duino Castle, just outside Trieste, is the seat of the Thurn and Taxis family and where poet Rainer Maria Rilke wrote his ‘Duino Elegies.’ Photo: Alamy

Walking along the footpath outside the castle and circling down to the waterfront, where a quiet bar-restaurant is built against the vertiginous, sloping stone, I reflected on Trieste’s nowhereness, the incongruity of spaghetti and Sacher torte.

As the child of an American mother and an Italian father, raised between New York, Rome and Paris, and with a blithe disregard for borders, I felt that Trieste, a place out of country and out of time, was the first city where I might truly belong. Its silent, cobblestone back streets provided the ultimate escape from the ceaseless chatter of city life—from reality itself.

On my final night in Trieste, I joined an acquaintance for a lyric tenor’s concert at the Teatro Verdi, a whirl of Austrian-style facades and gilded interior chandeliers.

The audience—mostly dowagers in velvets and silks—was muted.

But after the finale, the tenor reappeared for an encore.

“Per le spiagge, per le rive di Trieste,” he began, singing the opening lines of “The Bells of Saint Giusto,” a patriotic World War I paean to Italy’s victory against—and Trieste’s independence from—Austria-Hungary.

Oh Italia, oh Italia del mio cuore

Tu ci vieni a liberar!

Everybody sang along.

The Lowdown // Chasing the Ghosts of Empires and Authors in Trieste

Jason Lee

How to Get There: Several airlines offer connecting service from New York City to Trieste’s Dei Leigionairi Airport. Trieste is within a two-hour bus or train trip from Venice and Ljubljana, with frequent service from both cities.

Where to Stay: The art deco Liberty Residences, just off Piazza dell’Unità, best evokes the city’s air of fading grandeur (from about $90 a night with full kitchen, Via Armando Diaz, 14; residenceliberty.it/eng). For a full-on Habsburgian experience, the Grand Hotel Duchy d’Aosta, smack on the piazza itself, more than lives up to its aristocratic name (from $211, Piazza dell’Unità d’Italia, 2/1; grandhotelduchidaosta.com).

Where to Eat and Drink: Trieste is justly famous for its cafes. For lovers of pastries and strudels, historic Caffè San Marco has found the ideal balance between tourist attraction and locals’ cafe (Via Battisti 18, 39-040-064-1724). Caffè degli Specchi, on the main square, is more expensive but an ideal vantage point from which to watch locals on their passeggiata, or traditional afternoon stroll (caffespecchi.it). For heartier fare, traditional Triestine buffets like Da Pepi serve Austrian-style meats and cheeses for as little as $5 at lunchtime (Via Cassa di Risparmio 3; buffetdapepi.it), while trattorias like Da Massimo in the Roiano neighborhood serve up fresh harbor-caught fish; try the spaghetti barcolona, a regional specialty (Via degli Apiari, 4, 39-040-452-8821).