The forgotten Italian city on its way back to greatness

Standing atop Mount Giusto, surrounded by the remnants of the Roman forum, overlooking the expansive harbor and the azure Adriatic Sea, it's easy to grasp why Trieste was once among the globe's premier ports. So, why has it now faded into obscurity?

For centuries, Trieste was illustrious, Europe's primary portal to the Mediterranean, and a notable destination. Yet, when I mention it back in Britain, I'm usually met with blank stares. "Trieste?" they ask. "Where is that?"

That perception seems poised to shift. The last time I visited, five years ago, Trieste appeared as a tranquil backwater. Large cruise ships diverted from Venice due to restrictions are now docking here instead. After decades in the shadows, this ancient, disputed city is back on the tourism map.

Large cruise ships diverted from Venice due to restrictions are now Trieste's descent into obscurity because it was on the losing side in both World Wars. Before the First World War, it was the sole seaport of the Austrian empire. When Austria lost, it became Italian, but Italy had little use for it.

At the close of the Second World War, it was occupied by Tito's communists, who wanted it as part of Yugoslavia. The Western Allies disagreed, so from 1945, it lingered in limbo, governed by the UK and the USA as they deliberated its fate.

Ultimately, in 1954, Trieste was returned to Italy, stripped of its Istrian hinterland, which became part of Yugoslavia. During the Cold War, it was a dead-end town, enclosed by the Iron Curtain. When I first passed through here 40 years ago, on my way to Yugoslavia, it seemed like a place whose time had passed.

Much has changed. Yugoslavia is no more, and Trieste is a junction, not a dead-end. Its new neighbor, Slovenia, is in NATO and the EU. Its streets are bustling with sightseers, and the chatter in its bars and cafes is diverse, reminiscent of its Edwardian golden days when Britons traveled here by train to board steamers bound for the Far East.

Many modern travelers arrive on cruise ships, merely stopping for a brief exploration before moving on to another port. Yet, if you linger a bit longer, you'll discover another facet of Trieste – an enigmatic border town at the intersection of Latin, Germanic, and Slavonic cultures, still haunted by the ghosts of its Habsburg glory days, still distinct.

On my previous visit, I stayed at the Savoia Excelsior Palace – a grand hotel built just before the First World War. It’s historic and luxurious, in a prime position on the waterfront, but it felt more like a business hotel to me. This time, I wanted to unwind and explore the surrounding countryside, so I stayed at the Tivoli Portopiccolo, a coastal resort in Sistiana, 12 miles west of Trieste.

Portopiccolo is a modern development, nestled in a secluded cove with a sleek beach club and a marina full of stylish motor yachts. It reminded me of that popular TV show about an upscale resort. It's extremely comfortable and relaxing, but you feel somewhat isolated from real life. However, Sistiana is just around the corner, a practical harbor full of fishing boats and dinghies, with a stretch of pebble beach flanked by seaside shacks selling affordable food and drink.

The best way to approach the city is by boat, and during the summer there’s a ferry from Sistiana that takes you right into the heart of town. Tickets are affordable, and the journey is delightful. The surrounding coast is a long wall of limestone cliffs, thick with dark forest. It’s a dramatic sight, and the finest view is from the water. Eventually, the cliffs recede, and you sail into a broad bay, flanked by wharves and warehouses. Welcome to Trieste.

Over a century since the Austrians were driven out and the city became part of Italy, Trieste still feels more Central European than Italian. The cuisine is hearty, the architecture robust, and its cafes resemble those of Vienna. The locals are proud of their mixed heritage, and while Italian is the common language, everyone I spoke to emphasized their multicultural roots.

There is even some separatist sentiment. “Free Territory of Trieste,” proclaims a large banner on the Piazza della Borsa, one of Trieste’s busiest thoroughfares. “USA & UK come back!” I only met one outright separatist, far too young to remember when his hometown was administered by Americans and Brits, but nostalgic for that era nonetheless.

This regional identity adds another layer of interest to this elegant, intriguing city. It’s a metropolis in miniature – lively and attractive, yet small enough to navigate on foot (the population is about 200,000, around the same as it was a century ago, when the Austrians left). From the narrow alleys of the old town to the broad boulevards of the city center, it’s a pleasant place to wander, full of street life and human interest.

Trieste has no standout sights, and no must-see attractions. Its appeal is subtler, more discreet. The travel writer Jan Morris captured its cryptic aura in her melancholy memoir, "Trieste and the Meaning of Nowhere." James Joyce, who spent a decade here, cherished its understated charm.

The site that encapsulates Trieste’s moody ambiance is Miramare, a fairy-tale castle on a rocky promontory, battered by the restless sea. It was built by Maximilian, younger brother of the Austrian Emperor, Franz Joseph, but he barely spent a year here before being whisked away to become Emperor of Mexico. His quixotic empire was overthrown, and the republican rebels had him executed. Today, his forsaken folly is a museum, a monument to Habsburg hubris. It's believed to be bad luck to spend the night here. Several subsequent inhabitants also met untimely ends.

I ended up back where I’d begun, on Mount Giusto, high above the city. Most tourists climb to see the castle and the cathedral, but I came to see the mausoleum of Johann Joachim Winckelmann (1717-1768), the father of modern archaeology. Winckelmann wasn't from Trieste – he’d come here to catch a boat to Rome – but while here, he befriended a young man named Francesco Arcangeli, who murdered him for unknown reasons. Winckelmann was buried in the cathedral across the road. Arcangeli was executed in the city square below.

This eerie tale encapsulates what I love about Trieste. Everywhere you go in this elusive city, you're treading on layers of history – some recorded, much of it hidden. As I walked back to the harbor, past the Roman amphitheater, I recalled something Jan Morris wrote: “Here, more than anywhere, I remember lost times, lost chances, lost friends.” As the evening ferry carried me away, and Trieste shrank into the sea, her words resonated deeply.

Where to stay

I was a guest of Tivoli Portopiccolo Sistiana. Doubles from €300 per night, including breakfast. The room rate includes the use of the chic beach club. The house style is international rather than Italian. The entire resort is car-free (there’s a large underground garage). There are several restaurants on-site, in the hotel, and in the surrounding development. The best food I ate by far was in the beach club restaurant. It’s a good spot if you want seclusion, or if you’re traveling with children.

What to do – out of town

There are some decent excursions near Sistiana, most notably the Rilke trail from Sistiana to the Castello di Duino, a medieval castle where the poet Rainer Maria Rilke wrote his Duino Elegies. The clifftop hiking trail that bears his name snakes along the coast for several miles, offering stunning views over the Gulf of Trieste.

If you’d rather sit around and enjoy some local food, head for Bajta Salež, a family-run farmhouse restaurant and delicatessen midway between Sistiana and Trieste. They make their own wine and cure their own ham on-site. The family has strong Slovenian roots. The place is popular with locals, not just tourists. Eat in the gardens when the weather’s fine.

What to do – in town

Trieste has several splendid museums, housed in spectacular buildings. As well as the palatial Castello di Miramare, surrounded by lush gardens, and the Winckelmann Museum, with its eerie archaeological relics, don’t miss the Museo Revoltella, the opulent mansion of a rich merchant which now houses Trieste’s modern art museum.

Where to eat and drink

As one of Europe’s leading ports, with close trading links with South America, Trieste has always been renowned for coffee. Like the Viennese Kaffeehaus, a Triestine caffè is a virtual living room, a world away from high street chains. Caffè San Marco is the most historic, Caffè degli Specchi is the most ornate, but my favorite is Caffè Torinese, a quaint, antiquated hideaway where you can linger over a decadent cream cake, enjoy an espresso at the bar, or buy coffee beans to take away.

For an unpretentious meal, head for Buffet da Pepi, a local landmark since 1897. The décor is traditional, the service straightforward, and the menu is carnivorous. Afterward, take a walk around the corner to Gelateria Zampolli, a traditional ice cream parlor, for a refreshing gelato.