Spend some time in Borgo Teresiano, the orderly central neighborhood named for Empress Maria Theresa of Austria, under whose reign Trieste became the Austro-Hungarian Empire’s prosperous main port. To spur its growth, the Habsburgs declared it a free port and embraced religious tolerance — a legacy that still shapes the area today. Admire the district’s elegant Viennese-style architecture, stroll along the Grand Canal, and step inside the Serbian Orthodox Church of Saint Spyridon and the Greek Orthodox Church of San Nicolò. Don’t miss the massive bronze coin stamped with Maria Theresa’s face on Piazza del Ponte Rosso. Then take a 10-minute taxi ride to Antica Trattoria Suban, a century-old institution serving regional specialties such as basil-filled crepes and hearty goulash.

Sip your way through historic cafés

Trieste is Italy’s unofficial capital of coffee — home to the Illy empire and a café culture with its own local lingo (order a “capo in b,” a mini cappuccino served in a glass). Many of its most beloved coffeehouses date to the 19th century, when Trieste was the Austro-Hungarian Empire’s main port and coffee was big business. The three to know: Caffè Tommaseo, the oldest and most elegant; Antico Caffè San Marco, a literary landmark with its own bookshop; and Caffè degli Specchi, nicknamed “the city’s living room” for its rows of outdoor tables on Piazza Unità d’Italia facing City Hall. Before you sail, pick up a bag of beans from La Triestina, a local roaster since 1918, to recreate Trieste mornings back home.

Walk the Trieste streets that inspired Joyce

James Joyce lived in Trieste for more than a decade and wrote Dubliners, A Portrait of the Artist as a Young Man, and parts of Ulysses here. Trace his footsteps starting at Ponte Rosso, where a life-size statue of the author overlooks the Grand Canal – one of his favorite strolling spots. As you wander through the city center, you’ll encounter several of Joyce’s regular haunts: Teatro Verdi, where he attended opera performances; San Nicolò dei Greci, the Greek Orthodox church he occasionally visited; and Antico Caffè San Marco, his preferred hangout. Cap your exploration with a visit to the Svevo Museum, dedicated to Joyce’s close friend and protégé Italo Svevo, for deeper insight into the pair’s literary partnership.