By Clay Risen

Trieste may be the only city in Europe that appears more often in reflective essays than guide books or newspaper travel sections. Once the main port for the Habsburg Empire, today the city is most often overlooked by those making the Let’s Go Grand Tour. Even many Italians forget it’s there, tucked into a five-mile-wide hillside between Slovenia and the Adriatic.

But for those who have spent any time at all time in Trieste, there’s nothing else like it in the world. James Joyce moved there to teach Berlitz courses at age 22, and he stayed for 16 years; in the meantime he wrote most of Dubliners, all of A Portrait of the Artist as a Young Man and a good chunk of Ulysses. The British travel essayist Jan Morris, who recently published an elegy to the city entitled Trieste and the Meaning of Nowhere, writes that it "always seems to be on a fold in the map, hemmed-in, hole-in-corner" – and yet Morris, like so many others, keeps coming back.

With a population of just under 250,000, Trieste is one of a string of mid-sized, former Habsburg cities – along with Ljubljana, Zagreb, Graz and Pilsen – that have managed to retain their old-world charm in the face of constant political turmoil over the last 100 years. At the turn of the last century, Trieste was Austrian; later it was held by Italy, Germany, Yugoslavia and, in 1954, Italy again; before that it was held, alternately, by the Illyrians (its founders), the Romans, the Goths, Venice and Napoleonic France.

But while the city main church, the Cathedral of San Giusto, is built in a high Romanesque style, and while much of the southwestern section of the city is dominated by blank 1950s apartment blocks and heavy industrial eyesores, Trieste is still very much a Habsburg town. The city owes much of its architectural face to Austria’s Empress Maria Teresa; in fact, the center of downtown, hemmed in between the train station, the waterfront and the Colle de San Giusto hill, is called Borgo Teresiano, or "Teresa’s Quarter" (later annexations are named Borgos Giussepino and Franceschino, after Emperors Joseph II and Francis II).

Seeing in the city an opportunity to build her empire’s naval and merchant strength, the Habsburg empress expanded the port facilities and laid down a precise gridwork of imposing Viennese blocks and wide boulevards. Walk down Via XXX Ottobre and you might think you’re strolling somewhere just off Karlsplatz.

Alternately, you might find yourself recalling Vienna’s Café Central when seated in Café Tommaseo or Café San Marco, two of Trieste’s many gathering places in a city that takes its coffee extremely seriously (Illy, the premiere Italian coffee maker, is based there). Tommaseo, just off the water and around the corner from the vast Piazza dell Unita d’Italia, caters to a rather upscale, business crowd. San Marco (closed on Wednesdays) is full of students. Other cafes include Caffé Rex and Caffe degli Specchi. Triestino café culture is very much a nexus between those of Vienna and Rome – espresso is as popular there as it is anywhere else in the country, and drunk just as often. But like residents of other former Habsburg towns, Triestinos like to linger over their coffee, and they prefer comfortable chairs and well-decorated interiors to the stand-up, fast-food espresso ethos found in the Boot.

Unfortunately, perhaps the café with the greatest claim to fame is also one of those least traversed by the city’s latteratti, and for good reason. Caffe Pasticceria Pirona, located on Via Giosue Carducci at Piazza Carlo Goldoni, was a favorite of Joyce. But today it is overpriced and touristy; the baked goods are worth sampling, but there’s no atmosphere to speak of – and, seeing as how the place lacks seats, you wouldn’t spend much time there even if you wanted to. Trieste, does, however, offer more than few other pieces of Joyceana: There is a walking tour available from the tourist office, and every year at Bloom’s Day the city offers a series of lectures and readings related to Ulysses.

And while Joyce is certainly the most famous literary name associated with Trieste, many other authors and artists have crossed paths with the city. Italo Svevo, an acolyte of Joyce, was a native. Sir Richard Burton, the great traveler and Arabist, died here while serving as consul; Johann Winkelmann, the German neo-classical architect, was murdered in his room at the Locanda Grande hotel. Egon Schiele spent time in Trieste, and Rainer Maria Rilke wrote his masterpiece "Duino Elegies" while a guest of the Thurn and Taxis families at their Duino Castle, about 17 miles outside town.

Duino Castle is, unfortunately, inaccessible to the public, but closer in to the city is a royal residence even more stunning: Mirimar. Built in the 1860s for Prince Maximilian, brother of Emperor Franz Joseph, it is a lean white tower set at the edge of a cliff overlooking the Adriatic; behind it sits 54 acres of gardens and forest. Maximilian planned Miramar after he retired his command of the Austrian navy, but he never got to see it complete. In 1864 he left for Mexico to head up an ill-fated, French-led attempt to establish a new colonial regime there; they failed, and Maximilian was captured and executed. His wife Carlotta went insane with grief, and it is said that anyone who spends a night in Miramar will do the same.

While Trieste maintains its Austrian flair, today it is also a deeply diverse town. Croatians, Germans, Slovenes and Italians mix so readily that natives are virtually required to be bilingual. Until 1954 the city and its environs were Yugoslavian possessions, and Triestino food is inspired as much by the east as the west coast of the Adriatic. Bagutta Triestina, on Via Giosue Carducci near the intersection with Via Imbraiani, is a smallish, inviting restaurant with a number of house specialties drawn from regional cuisine. One bite of the truffle bruschetta will have you returning for every meal. Gnocchi is a popular standby in Trieste, but the city offers a wide variety of fare, from jota (sauerkraut and barley soup) to muset (boiled sausage with lentils and polenta).

Granted, this kind of fare isn’t for everyone, and neither is Trieste. It’s a blustery place, well-known for the bora winds that blow over the Karst highlands behind it and out to sea. There are no great museums or cathedrals, nor booming nightlife or labyrinthine canals (its one canal, the Canal Grande, is merely a 300-foot inlet, in reality neither a canal nor grand). But for those with the patience and insight, it offers up more subtle pleasures; as Morris writes, "Trieste on an autumn evening suggests the work of those English Victorian painters who specialized in seaports at the end of the day, with pale gaslight shining on wet pavements, and pub windows dimly illuminated." If you can find it on your map, it’s worth the trouble getting to, though once you’re there you may never want to leave.

Clay Risen is an assistant editor at The New Republic.  He lives in Washington, D.C.