Andrew Jerome

After waking up bright and early at 6:30 a.m., we packed up the last of our things and headed out to say goodbye to the friends we’d made on the cruise. Both Ken and Troy, and Kuamane and Nicholas were off to Venice, so we met them down at the Piazza for one last coffee and farewell. One of the reasons we love cruising is how quickly you can form connections in a setting like that — just a couple of weeks, and suddenly these people feel like old travel mates.

We grabbed a quick breakfast at the buffet — “quick” being generous. The whole ship seemed to have the same idea, and it felt more like a chaotic migration than a meal. Our disembarkation time wasn’t until 8:30 a.m., so we weren’t rushed, but I could’ve done without my bright idea to take the elevator instead of the stairs. Of course, it went all the way to the top before stopping at every deck on the way back down.

Once off the ship, we walked about 15–20 minutes through the city to reach our pre-booked apartment. The weather was warm but manageable, with a breeze coming in off the sea. Still, dragging wheeled suitcases over cobblestones and uneven pavements quickly became a workout. By the time we arrived, I was a sweaty mess — equal parts exhausted and annoyed. Thankfully, our host Alessia let us check in early, and things started looking up. The apartment was on the fifth floor, larger than our place in Milan, and had a kind of old-world grandeur. Alessia pointed out how many of the city’s buildings reflect Trieste’s Austro-Hungarian past — arched doorways once built tall enough to let horse-drawn carriages roll right in.

Once we settled in, we popped to a nearby supermarket to grab some essentials, then headed out on foot to explore. Our initial goal was to visit the Roman Theatre, but we were quickly sidetracked by the sheer volume of impressive architecture around us.

At Piazza Unità d’Italia, the scale and symmetry hit you straight away. With the Palazzo del Municipio anchoring one end and the Adriatic Sea framing the other, it’s Europe’s largest seaside square and feels every bit as grand as it sounds. The square is flanked by ornate buildings that speak of Austro-Hungarian pride, none more impressive than the Palazzo del Governo with its Liberty-style mosaics and stately arches, and the Palazzo del Lloyd Triestino — now the regional government building — where maritime sculptures nod to Trieste’s seafaring legacy. The grand Palazzo Generali, once the HQ of one of Italy’s oldest insurance firms, still presides confidently over the cafés that line the waterfront. The whole square feels regal yet relaxed, like a royal courtyard that accidentally became a hangout spot.

From there, we wandered past the Fountain of the Four Continents — a theatrical baroque piece from the 1700s featuring figures meant to represent Europe, Asia, Africa, and the Americas. The sculpted lion, crocodile, and horse perched alongside draped allegorical figures felt a bit like a marble theatre production mid-scene. Just around the corner, we found the Teatro Verdi, a neoclassical beauty that’s been standing since the early 1800s and still hosts operas under its dramatic façade.

We also passed the bronze sculpture of the Maria Theresa thaler — a giant coin bearing the profile of the Austrian empress who played a major role in developing Trieste as a free port. It’s oversized and a little cheeky, but it somehow fits the city’s sense of identity: rooted in empire, open to the world.

Next came the Serbian Orthodox Church of Saint Spyridon. With its five domes and richly detailed mosaics, it was impossible to miss. Built in the 1860s, its Byzantine Revival style is a real standout in a city better known for its neoclassical lines. A short stroll further brought us to the Church of Saint Anthony the Thaumaturge, with its impressive white portico and columns, almost Roman in appearance. It stands at the head of the Grand Canal like a sentry, watching over the pastel façades and café crowds that give the area its distinctly Venetian feel.

We finally made our way to the Roman Theatre, tucked into the edge of the modern city. Built in the 1st century AD under Emperor Trajan, it once held over 3,000 spectators. While it now sits quietly beneath apartment blocks and city traffic, it’s surprisingly well preserved — a reminder of just how far back Trieste’s history stretches. There’s something poetic about seeing ancient stone seats in the middle of a modern metropolis, still waiting for their next performance.

From there, we had one more goal for the afternoon: Miramare Castle. But before jumping on a bus out to the coast, we made a quick food stop. Just off the main drag, we spotted the quirky Maschera Fountain — a stylised theatre mask with water spilling from its tongue. It looks like something out of a surrealist play, but in a city where layers of culture overlap, it didn’t feel out of place.

I grabbed a kebab at Anatolia Kebab 12, mostly because we figured food options near the castle might be limited. Better to refuel now than end up staring longingly at closed snack bars in a royal garden.

We eventually found the correct bus stop — after a bit of back-and-forth across a fairly lively road — and managed to hop on just in time. What we didn’t manage to do was buy a ticket. I tried the app, Ted had a go at the onboard machine, and neither of us had any success. So we rode… accidentally free.

The ride out to Miramare Castle was scenic, skimming along the coast. And then the castle itself appeared — straight out of a fairytale. Built in the 1860s for Archduke Ferdinand Maximilian of Austria (who went on to become Emperor of Mexico, albeit briefly), the white limestone palace sits perched above the Gulf of Trieste with sweeping views and meticulously maintained gardens. We skipped the interiors, choosing instead to wander through the grounds. Sculpted hedges, fountains, grand staircases, and more than one dramatically posed horse statue — it was all every bit as impressive as the photos make it out to be.

Naturally, a gelato followed. You’re in Italy, it’s hot, there’s a castle behind you — it would’ve been rude not to.

On our way out, we bumped into the Southwest flight attendants from the ship — again. We’d already farewelled them that morning, then again just outside the terminal… and now here they were strolling near the castle. Deidre Chambers, what a coincidence!

Getting back into town involved another unsuccessful attempt at the ticket machine, which meant a second free-ish ride. We returned to the apartment for a well-earned breather before heading out again.

After relaxing back at the apartment, we decided it was time to find some dinner — without a plan, just a wander and see what called to us. Despite how much we’d already covered today, we somehow stumbled across more hidden gems — including seeing the impressive Palazzo della Borsa Vecchia (Old Stock Exchange) again, now housing the Chamber of Commerce. Its neoclassical columns and striking Neptune fountain out front made us stop for another round of photos. It’s like the city just keeps revealing layers the longer you walk it.

After a bit more wandering, we found ourselves at a place called Njoy — the words “burgers, burritos and tacos” on the menu made the decision easy. But the biggest surprise wasn’t the food — it was spotting The Americans again. What are the odds? Deidre Chambers would be proud.

They’re heading to Venice tomorrow, and we’re off to Ljubljana, so unless the universe is really playing games, that was probably our final run-in.

Since the evening still had some life in it, we wandered a little more, soaking up the glow of the city before stopping (yes, again) for gelato and picking up a few essentials at the supermarket.

Trieste turned out to be a real surprise. When I first started planning this trip, I’d thought about skipping it entirely in favour of somewhere more obvious like Venice. But I’m so glad we came here instead. It’s elegant without being overrun, full of history without being staged, and has a charm that feels both grand and relaxed.

Tomorrow: a day trip across the border to Slovenia — another new stamp on the travel list.Read more