Glenary’s bakery in the famous hill town of Darjeeling serves miniature flaky and ornate pastries arranged in rows that make you drool.

It was opened by an Italian called Vado—arriving from parts unknown—almost 100 years ago, during the time of the British Raj.

Located in one of the last stops before Tibet and the lofty forbidden lands of reclusive Buddhas, Glenary’s is the most unlikely exclave of Italian culture you could hope to find anywhere.

When I sat down to eat at Pasticceria La Bomboniera, a delightful artisan pastry café just back from Trieste’s waterfront, I might have discovered the kitchen where Vado served his apprenticeship.

No wonder these two bakeries gave me déjà vu.

The best cafés are usually just off major thoroughfares, and like Trieste itself, I’m glad I checked it out.

On the train from Venice to Trieste

I took the train from Venice Mestre to Trieste, as it’s the easiest way to get there.

Shortly after pulling out, the Julian Alps rose in the distance and ushered in some brief but heavy autumnal storms that made the train leak a little.

By the time I reached Gorizia, the Italian town bisected by the Slovenian border, the sun was shining again.

A little further along the line, I passed near the town of Prosecco, where the famous sparkling wine was first produced. Being a committed wine drinker, I dearly wanted to get off here and explore, but my train passed straight through.

Perched on a rocky promontory beneath Prosecco, Miramare Castle also flashed by. It’s a neo‑romantic cake decoration built by Franz Joseph’s younger brother, and again I had to settle for a mental note.

I wasn’t sure what looked more out of place here: the Habsburg-era palace or the monolithic cruise ships being fitted out along industrial quays bristling with Harland & Wolff cranes.

End of the line

To visit Trieste, you have to set out with the intention of doing so, as it’s an unlikely city to find oneself simply passing through.

The spit of coast it occupies is a narrow tract of land almost entirely circled by Slovenia and its lofty Karst Plateau that falls dramatically into the Adriatic Sea.

Unless you intend to leave Italy, there’s precious little Italian territory left to continue into.

Its improbability as a tourist destination is precisely what makes it so attractive to visitors with an aversion to crowds, and is the very reason I’m here.

And a rewarding destination it’s proving to be, too. The quality of the coffee is taken seriously, and I’ve been spoilt for choice with krapfen and strudel stands.

But I’ve found my spot, and although I’d like to linger at La Bomboniera a little longer, I sense that I’m unduly taking up a table, so I decide to move on.

Climbing up to the Karst

Due to my onward travel plans, I’ve booked an Airbnb in a small town high in the hills above Trieste called Opicina.

I don’t fancy the steep walk in the sticky late-summer heat, so I head over to the bus station to find a connection.

But while I’m great at thinking up original travel ideas, I have a poor head for travel details, and the confusing bus numbering spoils my good mood.

After sitting on a driverless bus for a few minutes, unsure whether it’s actually headed where I want to go, I give up and decide that the walk is the better option after all.

Poor choice.

The gradient quickly becomes ridiculous, the tarmac doubles the heat, and before long, I’m drenched with perspiration.

Usually, I’m like a fit elephant determined in its bloody-minded goals, but today I give in and call my host to come and drive me the rest of the way. I’m very glad I did, as it saved me a gruelling hike.

My host is a wiry young woman called Bianca with a poodle also called Bianca who drives a beat-up Renault Clio (the host, not the dog).

I dig her energy and her conversation too, but she’s soon gone, and I’m back to doing the boring stuff travellers have to do, like figuring out the Wi-Fi, the percolator, and the shower.

On the Yugoslav border in Opicina

A shower, mind, that ends up being one of the best I’ve had. When I’m done, I realise how far I appear to have travelled on that short drive.

The Airbnb is only a mile back on the plateau, but Trieste hasn’t followed me up here with its architectural grandeur.

My apartment is ample and few details have been spared, but it’s in a pre-fab three-storey tenement that’s the shape of an X. Surrounding me are identical X-shaped tenements, close-packed to maximise civic density.

I don’t mind the change at all—this is why I travel abroad. Yet the logic behind competing 20th‑century economic outlooks rarely shares the same hillside.

As it happens, my Airbnb sits right on the former border with Yugoslavia. Head to Opicina's tiny railway station and catch a train to Ljubljana, and you'll quite literally cross it.

Urban development here clearly followed a more utilitarian, border‑zone logic, accentuated by later Italian state pragmatism rather than any desire to pander to Trieste’s imperial past.

Within a surprisingly short distance, Trieste’s ornate Habsburg-era buildings have given way to dowdy, socialist functionality.

To celebrate my evening on this political fault line, I prepare an opulent cheese board, complete with some Slovene wine and a few indulgent savouries lugged across Friuli‑Venezia Giulia from the Italian supermarket chain Conad.

It’s very fun indeed to sit outside under the dim lamplight, picking at my table of delights while looking out across the balding gardens, watching boring domestic life continue in its stolid regularity.

As I sip my white wine, I wonder what it is about Trieste I felt earlier that I can’t quite put my finger on.

Trieste travel experience with a hint of espionage

It feels… clandestine. I haven’t been to Geneva, but I imagine it has Trieste’s uncanny sense of people minding their own business a little too well (make that another big tick for the crowd-averse visitor).

Despite only passing through, I trust my instincts about a place, and there are a few easily discoverable facts about Trieste’s history that might explain why it gives me spy vibes.

It’s a border city that keeps changing countries.

Since the collapse of the Habsburg Empire in 1918, Trieste has belonged to Austria‑Hungary, then Italy, then the Allied‑run Free Territory of Trieste (between 1947 and 1954), and finally Italy again.

In the devastating churn of 20th‑century geopolitics, Trieste has, in one decade or another, found itself aligned with Allied powers, Axis powers, and a communist Yugoslavia that belonged to neither NATO nor the Soviet Union.

It’s also a port city, and ships have brought more than cargo.

They brought sailors, merchants, intellectuals, novelists (James Joyce wrote the early chapters of Ulysses here), poets, and the occasional spy, feeding ideas into a city that has had to remain intellectually porous.

Finally, it’s a multilingual city. Italian, Slovene, Friulian, and German are all in circulation, meaning people can choose what they express to their neighbours and what they leave unsaid.

But as I’ve mentioned, I’m hardly a resident. My feeling might be because Trieste’s Art Nouveau skyline looks like somewhere the Broccoli family might choose to open a James Bond film.

Habsburgs and harbours

Having seen what I came to Opicina for, I catch a bus the following morning back down the hill into Trieste.

I try to pay with my contactless debit card, but it’s not accepted. A note for travellers in this region—you have to preload a travel card to pay your bus fare.

For my sincerity, I get a free ride and, with a day to kill, wander around Trieste’s traditional attractions.

The Piazza Unità d’Italia is as grand a place as you could hope to bring your beloved or recuperate under the sea breeze.

And the Habsburg façades around it rise grandly, but never feel imposing.

Before leaving, I walk to the end of the Molo Audace, Trieste’s famous pier.

A ship called the San Carlo sank in Trieste’s harbour in 1740. Instead of removing the wreck, the city authorities used it as the foundation for the pier.

To further commemorate local maritime identity, a bronze compass rose has been set into the stones at the tip of the mole, aligned with the cardinal directions.

Turning around, I take in the city’s entire skyline; the cranes fitting out cruise ships to the west, and frosted imperial city halls and museums along the waterfront.

A friend who sails in the Merchant Navy once warned me against visiting port cities due to the high turnover of heavy‑drinking temporary visitors and the establishments erected to cater to their tastes.

But Trieste doesn’t fit that archetype at all.

It’s elegant and gentle. Industrial, yes, but not in a way that defines it.

And I catch my train back to Venice with two boxed pizzas and a carton of Conad wine, too cheap to have earned the right to wash down last night’s cheese board.