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When Charles VI of Austria declared Trieste a free port in 1719 it was a small village with little history to speak of. The hill of San Giusto with its Roman theatre, its fine mishmash of a cathedral - the result of a fusion of two churches in the 13th century - and its bare Venetian fortress is all that the previous 2000 years have handed down to us. But in the 18th century, Trieste's position as Vienna's door to the rest of the world led to rapid expansion. Over the next two centuries the original Italo-Slovene population was swelled by a cosmopolitan mix of Germans, Croats, Greeks and Levantine Jews.
Trade did not have it all its own way, however. Trieste was a literary laboratory at the beginning of the present century: writers like Italo Svevo, Umberto Saba and the city's most famous Berlitz English teacher, James Joyce, found inspiration - paradoxically - in the city's commercially-oriented modernity.
Not enough history before 1918 was replaced by too much afterwards, as Trieste simultaneously became Italian and lost its livelihood with the carve-up of the Austro-Hungarian empire it had once serviced. Under Allied military government after 1945 - it was contested between Italy and Tito's Yugoslavia - the city became a UN protectorate in 1947, and was finally assigned to Italy in 1954, part of an isolated Italian thorn in the side of the Iron Curtain - a symbolic position which pleased the city's active ultra-nationalist political groups, but made its status as a port quite untenable.
Recent years have seen signs of an upturn in the city's fortunes with the freeing up of Eastern European trade and the development of light computer-based industry in Trieste's Carso hinterland. Some of its special status remains: local residents pay half as much for petrol as Italians in the rest of the country - a measure introduced to stop them popping across to cheaper Slovenia to fill up. And many triestini still consider themselves to be closer in cultural background and temperament to Vienna than to Rome.
Trieste is at its best in spring and autumn, away from the humid summer heat and the often severe winters, when the biting bora wind can blow so hard that makeshift rope handrails need to be strung along the steepest streets.
Getting around
The nearest airport is at Ronchi dei Legionari, about 30km west. A bus service into the town centre is timed to coincide with all incoming flights.
All the city's main sights are within easy walking distance; a good network of buses serves out-of-town destinations such as Miramare or the fishing village of Muggia. Taking the cable tramway up to Villa Opicina, with its view over the whole sweep of the bay, is an excursion in itself. A ferry service (daily except Tues) connects Trieste with points on the Istrian coast of Slovenia; there is also a twice-weekly car ferry to Greece.
Where to stay
For fin de siècle luxury, stay in the four-star Grand Hotel Duchi d'Aosta on the central Piazza Unità d'Italia - a huge, theatrical open space bordered on one side by the sea and on the other three by an ostentatious display of the city's moneyed, neo-classical architecture. A cheaper option on the corner of the square is the comfortable two-star Al Teatro - though beware the lack of air-conditioning in the summer months.
Summer is when the three-star Riviera Residence Maximilian comes into its own. Situated in Grignano, 8 km along the coast, just beyond the fairy-tale castle of Miramare, it has its own private beach, which you get to by taking a lift down from Reception. The rooms are bright and airy, and there is a charming terrace bar overlooking the sea.
But budget travellers can enjoy almost the same setting for a fraction of the price. On the Miramare access road is a youth hostel with a location a five-star hotel would die for: overlooking the beach, with its own lively terrace bar. Only the private lift down to the beach is missing.
Restaurants
Triestine cooking is essentially Italian with the occasional Austrian and Slovenian influence, which makes itself felt especially in the city's buffets - cheap eateries offering pork cuts, sausages and sauerkraut. Seafood also features strongly - to try it at its best, head out along the bay to Muggia, a pretty, Venetian-style fishing village right on the border with Slovenia.
Al Bagatto in Via F. Venezian 2 is one of Trieste's more dependable restaurants, with a neat line in pre-prandial cocktails and an excellent wine list. It's one block back from the sea, and the marine influence is felt in dishes such as their triumphant fritto misto - a cut above your usual seaside trattoria fry-up. Signed testimonial photos by the likes of Maradona line the walls. For lunch, La Piola in Via San Nicolò 1b is a good bet. By day this cool refuge, in the street where Joyce used to live, offers a selection of reasonably-priced pasta dishes and generous salads. In the evening the atmosphere, and the food, is more elegant and formal - though even then it's difficult to spend more than L40,000 a head.
Cafés and bars
If you suddenly come over all Austro-Hungarian, head for one of Trieste's historic cafés. The Caffè San Marco in Via Battisti 18 should give you a fix of langour, malaise and Art Nouveau decadence to last a lifetime. Wispy damsels gaze down from ceiling frescoes, red velvet drapes shut out the sun, and acres of mahogany and brass set the right penumbral tone. You might even catch an intense chess match in progress at one of the central tables. The coffee is good too.
Lighter and airier but equally atmospheric is the Caffè Tommaseo in Piazza Tommaseo, near the port. Established in 1830, this symphony in stucco, Murano glass and mirrors has always been one of the places to see and be seen. Rich merchants would conduct important business at the pavement tables while keeping an eye on their cargoes.
Leafy Via XX Settembre is so choc-a-bloc with bars and gelaterie that pavement tables in the central pedestrian island are colour-coded. Pipolo is a good bet for ice-cream.
Shopping
The borgo teresiano - the grid-pattern, neo-classical city centre named after Empress Maria Theresa - is where Trieste's generally uninspiring shopping opportunities are concentrated. Forget about shoes and clothes and concentrate on coffee and second-hand books - two commodities which the city specialises. Even if you haven't got the espresso machine with you, a bag of freshly-ground coffee is a great travelling companion; try the CremCaffè, an old-fashioned torrefazione (coffee roaster) on Piazza Goldoni, where you can also pick up a set of limited edition Illy coffee cups (the design changes every year).
The old town, between Piazza Unità d'Italia and the hill of San Giusto, is dotted with second-hand bookshops. One which is so famous as to feature on the city council tourist trail is the Libreria Antiquaria Umberto Saba in Via San Nicolò 30. Set up by the city's most famous poet in 1919, it still retains the musty, order-through-chaos atmosphere of a true bibliophile's den. James Joyce lived with wife Nora and two kids in a flat above, though he and Saba never met.
Museums
In Trieste itself, the Museo Revoltella stands head and shoulders above the rest. Literally, too: the museum's modern fifth and sixth floor extension is a great place to watch the sun set from the terrace bar. Inside, there is a good collection of 20th century Italian painting - Sironi, Carrà, De Chirico, Capogrossi - plus some interesting local painters, including a fine series of portraits of Triestine merchants and their families by Gorizian painter Giuseppe Tominz. Piped Mahler sets the right mood. The museum organises temporary exhibitions and a series of evening films and concerts in summer.
The Museo Morpurgo in Via Imbriani 5 is a curiosity: an authentic (though rather frayed-at-the-edges) example of a late 19th century nobleman's residence, complete with original furniture, paintings, and creaking parquet floors.
Six things to do
•Take the 36 bus 7km along the coast to Miramare, the wedding-cake castle commissioned by poor old Maximilian, younger brother of Emperor Franz Josef and briefly (thanks to Napoleon) Emperor of Mexico. The castle and grounds were completed only in 1870, three years after Maximilian was shot by a Mexican firing squad outside the theatre of Queretaro, where he had been tried in front of a paying audience. Admire the kitsch imperial rooms, stroll in the enchanting gardens, or come in the evening for a son et lumière spectacular.
•In summer, cool down in the world's largest visitable cave, in the Carso limestone plateau behind Trieste. The Grotta Gigante in the Borgo (village) of the same name is 107 metres deep and 280 metres long, and the temperature inside is a steady 11 degrees all year round. So high is the roof that the stalagmites look like fossilised palm trunks - an effect caused by the spread of the drops on impact. A good way to get there is to take the scenic cable tramway to Opicina, then the 45 bus.
•Another thing to do in the Carso is to find an Osmizza and quaff local wine with your Slovene host, while snacking on his farm produce - home-cured ham, cheeses, olives and home-made bread. Osmizza derives from the Slovene word for "eight" - referring to an Imperial edict which allowed peasants to offer their produce to paying guests for eight days a year. The regulations are more relaxed now, but opening is still seasonal - look for the leafy branch nailed to the gate, or buy a copy of the annual Guida alle Osmizze, on sale at newspaper stands.
•Take the train along to Sistiana and walk along the Rilke footpath, named after the German poet who stayed in Duino castle between 1911 and 1912 (it was here that he wrote the famous "Duino Elegies"). The limestone cliffs along the way are eroded into strange, ribbed formations and there are some marvellous views along the coast.
•Trieste is a centre for fans of operetta, due to its long association with Franz Lehár, the Hungarian composer of the Merry Widow. Every summer in July and August aficionados flock in for the Festival of Operetta, which is held in various venues, including Miramare.
•A more sombre experience is offered by the Risiera di San Sabba, on the outskirts of town in the Ratto della Pileria 1. This rice-hulling plant was converted into the only concentration camp on Italian soil in 1943. A permanent exhibition commemorates the estimated 20,000 people who died here.