Known as the “little Vienna by the sea” for its grand buildings, impressive square, rich cafe culture and glorious waterfront lined with neoclassical architecture, Trieste is a place like no other in Italy. An important port of the Habsburg Empire, the capital of Friuli Venezia Giulia sits at the end of the Adriatic surrounded almost entirely by Slovenia. It has spent more time being Austrian than Italian, and its Triestini dialect is a mix of Italian, Austrian-German, Greek and Croatian.

Trieste’s fascinating history and diverse ethnicity and religion can be seen everywhere – from the ruins of the Roman amphitheater to the medieval stone fortress and cathedral above the old town, from the magnificent neoclassical synagogue to the towering white Greek and gold mosaic Serbian churches.

The city loves its literary connections, the most famous being James Joyce, who stayed here from 1904 to 1920 and is remembered with both a statue and museum. The Joyce and Svevo Museums in the city’s public library celebrate the Irish writer’s work and that of another literary great, Italo Svevo. It was in Trieste that Joyce honed his craft – or as fellow Irish novelist Colm Toibin wrote where, “Joyce grew up” – penning his early work and drafting Ulysses, the novel that was to change the course of modern literature.

Trieste is where most of Italy’s unroasted coffee beans arrive and the city loves lingering over a capo in B (a mini cappuccino served in a bicchiere, or glass) on Piazza dell’Unità d’Italia, the country’s largest sea-facing piazza. The Triestini are also fond of their local Friuli Venezia Giulia wines, and are partial to a cocktail or two with the once-seedy alleys of Cavana’s red-light district buzzing with bars and restaurants at aperitivo hour and into the night.Here, we have gathered the best wineries, cuisines, hotels, and things to do that stretch from the cliffs of Carmel to the coast of Santa Barbara. Get your stemware ready.

24 HOURS IN TRIESTE

Felix Jermann, of the historic Friuli Venezia Giulia winery, grew up in the region and began exploring Trieste day and night in his teens. He shares his little black book.

What’s the first thing you do when you arrive in Trieste?

Have a swim in the sea in the Barcola area, it has the best waters of the region in my opinion.

Do you have a favorite spot for lunch?

Dama Bianca, an old-school, classic fish restaurant 15 minutes from the city in Duino, where you can enjoy the seaside views. Here it seems time has stopped. I may have a cocktail too. There is a lovely cocktail bar right next to it, where the restaurant owner Dario mixes up a great drink. This is also a good spot for a swim.

For someone new to the city, which area would you recommend to walk around for a unique Trieste experience?

The city center is definitely the prettiest, with its main square going right up to the sea front – the only one in Italy built in such a way. You can enjoy some of the best sunsets from here too.

Is there a particular museum or a gallery you like to visit?

If the weather is nice, I have a walk in Miramare, and see the castle and its gardens. It’s so charming.

Where would you recommend for an early evening aperitivo?

The Pier for a casual sunset aperitif. For something fancier, Harry’s Piccolo Bistro. Ask them for an espresso martini as Felix Jermann takes it – they will know. Or any bar that you see people outside is a safe bet in Trieste for an aperitif.

And for dinner?

For something classic and authentic, Chimera di Bacco; or Orfanelli for a more rustic and traditional experience.

For a traveler with a passion for wine, which would you say are the most interesting wineries, apart from Jermann, in Friuli Venezia Giulia?

In Trieste, you have to visit Zidarich and Kante, two distinct expressions of the Carso Terroir. Over the Collio and Brda hills, I would check out Toros or Russiz Superiore on the Italian side of Collio. Then on the Slovenian side, you should definitely visit Movia, Edi Simčič and Marjan Simčič.

Do you have a favorite place to eat in Friuli Venezia Giulia?

My favorite would be at my grandmother’s restaurant, the Trattoria alla Luna, for authentic, traditional yet contemporary Mitteleuropean cuisine. For something more fancy, which serves traditional Friulian cuisine, La Subida’s Ristorante al Cacciatore.

Jermann

One of Italy’s touchstone producers makes wines of precision and polish.

Livio Felluga

The pursuit of quality can be seen in the elegant wines.

Miani

Winemaker Enzo Pontoni makes iconic wines in small productions.

Gravner

Characterized by a low-interventionist approach in the vineyards and cellar.

Edi Keber

Expressing a deep belief in the unique character of the Collio terroir.

Harry’s Piccolo

A Michelin-starred restaurant on Trieste’s Piazza dell’Unità.

Siora Rosa

A beloved Trieste institution serving Germanic and Hungarian classics.

Vitello d’Oro

Udine’s oldest restaurant specializes in seafood cuisine.

Mondschein

A gorgeous Sappada restaurant that balances tradition and innovation.

Tavernetta all’Androna

This elegant venue in Grado enjoys a tiny piazza to itself.

Grand Hotel Duchi D’Aosta

Trieste’s grand dame is opulent if traditional.

Palazzo Lantieri

A historic address in Gorizia (Goethe and Casanova stayed here).

Falisia Resort & Spa

A coastal retreat with views of Portopiccolo’s marina and bay.

Albergo Alla Spiaggia

A modernist building in Grado set between city and beach.

Picech

The Collio winery and agriturismo offers a Vespa to explore the farm.