Spend your first day getting to know the city. Join a walking or bus tour through the historic center, home to Roman ruins, Hapsburgian palaces, and the grand Piazza Unità d'Italia—testaments to the city’s long history under a variety of different ruling empires and dynasties. Afterwards, tour the beautiful 19th-century Miramare Castle on the Gulf of Trieste, just north of the city: Purchase skip-the-line tickets, or take a guided tour through the castle’s lavish period interiors and the sweeping grounds and botanical gardens overlooking the Adriatic Sea. 

In the afternoon, take a deep dive into Trieste’s unique cuisine with a cooking class or a demonstration in a local home featuring dishes like Trieste-style goulash, followed by dinner. End your day with a leisurely coffee and pastry at a historic café like Caffè degli Specchi, in Piazza Unità d'Italia, or Caffè San Marco, on Via Battisti.

For centuries, Trieste was part of the country of Austria-Hungary, as was neighboring Slovenia. To fully understand the city’s culture, take a day trip across the border, where there are a number of destinations that make for easy excursions. Lake Bled, which sits in a dazzling alpine landscape, is one of the most popular. This glacial lake next to the 12th-century Bled Castle has a picturesque island with a spire-topped gothic church. Many tours combine a visit to Lake Bled with a stop in nearby Ljubljana, Slovenia’s capital city. 

Alternatively, join a tour of Predjama Castle and Postojna Cave, both located an hour from Trieste. The striking 13th-century castle was constructed on the side of a vertical cliff, inside a towering cavern, which is part of the same karst cave system as the nearby Postojna Cave. Among the largest karst caverns in the world, the Postojna Cave is so immense that it must be toured via an electric train. 

Trieste is the capital of Friuli-Venezia Giulia, which is known for lush, rolling countryside. Focus on these vineyard-covered hills on your final day with a wine tour in Collio, an excellent way to sample local Pinot Gris, Pinot Noir, Pinot Blanc, and Ribolla Gialla wines in cellars dating from the 12th and 13th centuries. Learn why the microclimate of this stretch between the Dolomites and the Adriatic Sea produces such unique wines, and stop for a traditional lunch. 

For those who would rather explore another city in this region, there’s Udine, which offers a beautiful medieval center peppered with a mix of architectural styles as well as squares lined with lively restaurants and cafés. Alternatively, head to the neighboring region of Veneto, and spend the day in Venice, admiring St. Mark’s Square, the Grand Canal, the Doge’s Palace, and other top attractions.