It’s a December evening in Trieste. The city’s immense Piazza Unità, which runs from the edge of the Adriatic to the city’s town hall, is aglow, lined with decorated Christmas trees and illuminated façades. The name Unità, or unity, is well suited for the place of Trieste’s civic structures and reflects the city’s history as a crossroads of Germanic and Slavic borders. Once a great port of the Austrians, Trieste didn’t come under modern Italian rule until 1920, and its status remained tenuous throughout WWII until an agreement settling a longstanding border dispute with Yugoslavia was reached in 1975.

As challenging and uncertain as Trieste’s past might have been for its residents, it became a multicultural, multiethnic and multilingual city—a kaleidoscope of architecture, cuisine and color.

Trieste is, as a mayor of the city once put it, “the eastern edge of Latinity and the southern extremity of Germanness.” Unfamiliar territory even to many Italians, it’s tucked away near the border of Slovenia. It looks out at the Gulf of Trieste and the blue waters of the Adriatic, and the rugged limestone heights of the Julian Alps tower over it from the north. In this far corner of Italy, Trieste has long been overshadowed by the more regal and bejeweled city of Venice to the south. It was, in fact, because of two centuries of ongoing battles with the Venetian Republic, that the burghers of Trieste turned to Leopold III, the Duke of Austria, for protection and were incorporated into his empire in 1382. Under the rule of the Habsburgs, Trieste enjoyed an era of vibrant cultural growth and economic expansion. As the main port for the Austrian Empire, the city became a hub of commerce and a magnet for architects, musicians, artists, soldiers and merchants.

Part of Trieste’s charm is the layers of its past, evident in buildings like the ancient San Giusto cathedral. Built on the site of a Pagan temple, additions were made to the church over the years, starting as early as the sixth century. It now houses the remarkable apsidal mosaics depicting Our Lady of the Assumption and San Giusto that were laid by master Venetian craftsmen in the 12th and 13th centuries.

It’s a city that takes on multiple personalities as you walk from the quaint streets near the Serbian Orthodox church, reminiscent of Prague, to the grand streets of the Habsburgs, organized for their ornamented banks, office buildings and civic structures. The Teatro Giovani Verdi, Trieste’s 200-year-old grand opera house, is another hallmark of a bygone era. Its Neoclassical façade is reminiscent of La Scala in Milan, and its opulent interior harkens back to the gilded age of the Austro-Hungarian Empire. Tradition lives on here during the annual Festival of Light Opera, which draws international audiences and performers.

Architecture wasn’t the only import to Trieste. The Viennese café became a staple of the intellectual scene and fit right in with the gaslit mystique of the narrow cobblestone streets. James Joyce could often be found holding court with his literary set, including Italo Svevo, at any of a number of cafés like Caffè San Marco, Caffè Tommaseo and Caffè degli Specchi, that have been around since the 1800s. Another café, the Caffè Pasticceria Pirona, was Joyce’s favorite pasticceria, and he would spend hours there eating Austrian style pastries, or maybe thick slices of presnitz, and working on pages of Dubliners or Ulysses.

The mood of Trieste is set in its bustling Viennese cafés, and written on the elegant Neoclassical façades. If you take an evening stroll along the pedestrian promenade next to the Canal Grande, or dine on the hearty regional cuisine like jota or lasagna ai semi di papavero in one of Trieste’s many restaurants, you find an enchanting city with unique character and interesting flavors.

For those looking for day trips into surrounding Friuli-Venezia Giulia, Trieste is a great springboard. In the nearby town of Udine, the 18th century frescoes by Giovanni Tiepolo in the Episcopal Palace are stunning. The ancient town of Aquileia is the site of archeological remains that continue to be excavated and is thought to be the largest Roman city yet to be unearthed.

Hotel Filoxenia
A family-run hotel right by the water with 20 contemporary rooms, its restaurant offers authentic Greek cuisine. Via Mazzini 3, Trieste, 34121, tel. 0403.48164, double room 100 euros, filoxenia.it.

Hotel Residence L’Albero Nascosto
Part of a project to restore Trieste’s ancient historical center, rooms here are small apartments with kitchens and modern touches, including paintings by local artists. The hotel also has an on-site wine bar. Via Felice Venezian 18, Trieste, 34124, tel. 0403.00188, double room 105 to 155 euros, alberonascosto.it.

James Joyce Hotel
Located in the city’s historical center, the building dates back to 1770, and the hotel has 12 charming rooms. An on-site dining room serves breakfast daily. Via dei Cavazzeni 7, Trieste, 34121, tel. 0403.11023, double room 80 to 110 euros, hoteljamesjoyce.com.

December 2008