Known as the Gateway to Zion for its role as a point of emigration to Palestine, this sophisticated, cultured city teems with literary significance and World War II-era history, and its Israelite Temple is one of Europe’s largest synagogues.

Trieste is an Italian city that defies expectation. Called Vienna by the Sea, it is as much Austrian as it is Italian, from its fin-de-siècle cafés to its neoclassical and Baroque architecture, from its Central European cuisine to its neighborhoods arranged in a grid and named for Austrian emperors. Trieste—in the northeastern tip of Italy, near Austria and bordering on Slovenia—was the first Italian city to stage a Richard Wagner opera and to introduce Sigmund Freud’s ideas.

A port city with a seemingly endless Adriatic shoreline that attracts sunbathers galore, Trieste rises from the sea on majestic hills. But many of its attractions, including block-long palazzos and a renovated medieval quarter with narrow lanes just an arm-span wide, are on level ground near the sea.

The nicest things about Trieste are its relatively small size (population about 237,000) and its relaxed atmosphere. It is a perfect base for exploring northern Italy, including Venice (less than 100 miles west), and mountainous Slovenia.

History
The first written mention of a Jewish presence in Trieste is in the 14th century. After this tiny village came under Austrian protection in 1382, German Jews settled there, engaging in moneylending, banking and trade. In 1697, Trieste’s 60 Jews were forced to live in a ghetto.

To create a mercantile empire, the Hapsburg rulers declared Trieste a free port in 1719. Jews, including some from Corfu, came to trade there. The 1782 Edict of Tolerance issued by Emperor Joseph II provided freedom of worship and lifted other restrictions, and in 1785 the ghetto gates came down. By 1788, 670 Jews lived in Trieste, and the number grew steadily to nearly 6,000 in 1938. The city had four synagogues, two of them Sefardic, in addition to the great synagogue—the Israelite Temple—built in 1912.

Around the turn of the century in Trieste, then a cosmopolitan port city where many languages were spoken, Jews were involved in a cultural revolution of sorts. Edoardo Weiss introduced psychoanalysis to Italy, and his Jewish-born literary friends, Italo Svevo and Umberto Saba, helped spread the word. James Joyce, who lived in Trieste from 1904 to 1915, became a close friend of Svevo and based the character of Leopold Bloom in Ulysses largely on him. Jewish artists, too, became prominent.

Jews were also involved in high finance and the establishment of the major insurance companies in Trieste, especially Assicurazioni Generali.

But growing anti-Semitism in the Austro-Hungarian Empire moved some Jews to join the nationalist Italian Irredentist movement, which aimed to unite all ethnically Italian people and to reclaim from the empire Trieste, Gorizia and Gradisca. In 1919, the Treaty of Versailles satisfied most of these claims, but Trieste lost its economic importance.

Both before and after World War II, Jews had made the port a gateway for immigration to Palestine—so much so that Trieste was dubbed the Gateway to Zion. But with the rise of Nazism and the concomitant increase in the number of Central European Jews seeking to escape through Trieste, local Jews’ allegiance to Italy came under suspicion.

By the early 20th century, many Jews had converted to Catholicism, several because they married Catholics. Under Fascism, a significant number of Jews tried to remove their names from the Jewish registry, some, again, through conversion. In 1938, Italy enacted racial laws barring Jews from schools and employment. In 1942, Jews were forced to perform slave labor. Many used the emigration networks they had established to reach Palestine.

From October 1943, when only 2,300 Jews remained in the city, Nazi attacks began. A large number of Jews were taken to Risiera di San Sabba, the only concentration camp in Italy, on the outskirts of Trieste. Some were killed there; 710 were deported to other concentration camps. Only 20 Jews returned.

Community
Though Trieste now has fewer than 600 Jews, the community employs a full-time rabbi and holds regular Orthodox services at the Israelite Temple, one of Europe’s largest synagogues. Some 20 people, including a handful of visitors, attended a Friday-night service there in June, led by the rabbi and three young men with booming voices.

Many Jews fill high-ranking positions in Assicurazioni Generali. Others are lawyers, doctors, university professors, teachers and shop owners.

The community (www.triestebraica.promotrieste.it) operates a day school, an old-age home and a full complement of organizational activities. Although the synagogue hosts Israel-oriented activities, some community activists are openly critical of Israel.

Sights
Start at the rectangular Piazza dell’ Unita d’Italia, with its tourist information office (011-39-40-347-8312; www.turismofvg.it); its Café degli Specchi, where Joyce, Svevo and Saba sat; and its palazzos housing local government. Facing the sea is the eclectic-style Town Hall, topped by a Central European clock tower. The Assicurazioni Generali building on the left belongs to the company founded by Giuseppe Lazzaro Morpurgo, a Jew, but the company headquarters are elsewhere.

In 1938, Benito Mussolini moved the Fountain of the Four Continents from in front of Town Hall and had a platform erected so he could announce the introduction of the racial laws. In 2000, the fountain—representing the continents known in the mid-18th century, when sculptor Francesco Mazzoleni created the piece—was returned to its original position.

At the northeastern corner of the piazza, cross Capo di Piazza and pass through Passaggio del Portizza to Via delle Beccherie. This is the site of the latter and larger of Trieste’s two ghettos, established in 1696, where Jewish-owned antique shops can still be found. This street runs into Via Tor Bandena, where two synagogues once stood.

Turn left on Via del Teatro Romano. The poet Umberto Saba, originally Umberto Polli, was born in a building that stood on this corner. Turn right on Corso Italia and turn right again on Piazza Silvio Benco. Just up Via del Monte was the old Jewish cemetery, established in 1446. It is mentioned in Saba’s poem “Tre Vie” (“Three Streets”), verses from which appear on a plaque on a yellow stucco building next to the Via del Monte street sign. The cemetery site became a memorial to World War I dead.

The stone edifice at 5 Via del Monte, once the Jewish Agency building through which passed thousands of emigrants for Israel, houses the Carlo and Vera Wagner Museum of the Jewish Community (011-40-633-819). Exhibits include a large Torah crown and a pair of Torah finials ornamented with musical instruments, including a violin and a lute. These 17th-century items are from Ancona, in central Italy.

One room is devoted to the Holocaust: On display are jewelry and other items—each tagged with its value in Reichsmarks—confiscated by the Nazis.

Next to the museum is Trieste’s Jewish day school (39-40-638-008).

Return to Corso Italia, cross it and turn right onto Via Dante Alighieri. At the corner with Via San Nicolo, at No. 30B, stands a bronze sculpture of Saba striding across the street. The antiquarian bookshop Saba owned, at 30 Via San Nicolo, has first editions of his poems.

Return to Corso Italia, turn left and walk two blocks to Via San Lazzaro. At No. 8 is a plaque marking the location of the home and clinic of Weiss, Freud’s disciple.

Now walk east on Via Mazzini to the corner of Via Imbriani. The house at No. 5 was the Renaissance-style palazzo built in 1870 by two Morpurgo sisters, Emma and Fanny. The second floor has become the Morpurgo Family Museum (39-40-636-969). Most of the original furnishings and paintings are intact. A ketuba hangs in the parents’ bedroom, but a depiction of the Last Supper is displayed in the bedroom of a daughter who married a Catholic.

The first floor houses a small art museum, Civico Museo di Storia Patria. Among the exhibits are small nature drawings in pastels by Jewish artist Gilda Nadia Goldschmied (1894-1971).

Next, walk north on Via Imbriani and cross Via Carducci to reach Viale XX Settembre. No. 16 is the birthplace of Svevo, born Ettore Schmitz. Take Via Xydias to Via Battisti and turn right to Café San Marco at No. 18 (39-40-363-538). Established in 1914, this Viennese-style café, with dark wood paneling and ceilings carved with a coffee-leaf motif, was a favorite meeting place for intellectuals, literati and Irredentists, many of them Jews. To this day it hosts literary events, and Jews often meet here before or after synagogue services.

Now walk one block on Via Donizetti to reach the Israelite Temple (19 Via San Francesco; 39-40-371-466), a magnificent domed edifice built of reinforced concrete. Architects Ruggero and Arduino Berlam followed a 4th-century C.E. design found in Syria. The faux-stone exterior has clean rectangular slabs with little ornamentation (except for a large rosette window), but the interior is richly detailed.

The ziggurat-shaped Ark is inspired by Babylonian motifs, and the golden mosaic over the Ark is meant to recall Solomon’s Temple. The faux-marble walls are topped by a colorful floral mosaic. The marble railing surrounding the Ark is decorated with ears of corn, the symbol of the Trieste community. Most services are held in the synagogue’s small chapel.

Now walk southwest on Via San Francesco, cross Via Carducci and continue on Via Torrebianca, stopping on Via XXX Ottobre to visit La Bomboniera at No. 3A (39-40-632-752), an old-fashioned pastry shop once owned by Jews. The shop sells Austrian cakes typical of Trieste and, though it is no longer kosher, it still produces marzipan treats for Purim: montino, a cone-shaped sweet combining chocolate, maraschino and rum flavors; and salamino, chocolate-glazed marzipan that is sliced like a salami.

Turn right on Via Paganini (which becomes Via Rossini) and walk toward the sea. On the left is a sculpture of James Joyce on the Red Bridge over the Grand Canal. The block-long beige palazzo on the right was a wedding gift of the Hirschel family, owners of the opera house, to their son in the mid-19th century. On this building, at the corner of Via Filzi, is a plaque honoring Empress Maria Theresa in several languages, including Hebrew.

When you reach the sea, turn right on Corso Cavour, which becomes Viale Miramare, to reach the train station. Two bronze memorial plaques commemorating those deported from Trieste by the Nazis can be found on Via Flavio Gioia, a side street between the train station and the bus station.

Another walk starting at the southeastern corner of Piazza dell’ Unita leads to the older ghetto. Follow Via San Sebastiano south, turn left on Via dei Capitelli and left on Via Trauner—a narrow alley—to the end. The gray, yellow and white buildings in this cul de sac constituted the first ghetto.

From Via dei Capitelli walk southwest to Via del Madonna del Mare and turn left. No. 13 is a public library that houses the Italo Svevo Museum (39-40-359-3611; www.museosveviano.it) and the James Joyce Museum (39-40-359-3606;www.retecivica.trieste.il/joyce).

Return to Via San Sebastiano and turn left (here it is called Via di Cavana) and right on Via San Giorgio. At Piazza Hortis, stop to see the bronze sculpture of Svevo in front of his beloved public library. Then continue on Via San Giorgio to reach the Revoltella Museum–Gallery of Modern Art (27 Via Diaz; 39-40-675-4350), housed in what was once the palazzo of Baron Revoltella. The works of five Jews are displayed prominently: Arturo Nathan (1891-1944), Gino Parin—born Federico Pollack (1876-1944), Vittorio (Haim) Bolaffio (1883-1931), Arturo Rietti (1863-1943) and Isidoro Gruenhut (1862-1898).

The Jewish cemetery, dating back to 1843, is in the southern part of the city (4 Via della Pace). In death, as in life, Trieste’s wealthiest families, including the Morpurgos, are housed in lavish structures. On the site is a Holocaust memorial, twin pillars of stone inscribed with area victims’ names. Interred in the cemetery are Elio Schmitz (the brother of Svevo) and Umberto Beniamino Steindler, the ship captain who, during the 1930s, brought 150,000 Jews to safety in Haifa.

About one mile southwest of the cemetery is the Museo della Risiera di San Sabba (5 Via Palatucci; 39-40-826-202;risierasansabba@comune.trieste.it). In 1943, the Nazis transformed the one-time rice-husking facility into a transit/prison camp and extermination site as well as a storehouse for confiscated goods. Partisans, Jews and other opponents of the Nazis were tortured and executed here, and their bodies were burned in a crematorium. The museum contains explanations in English about why the Nazis invaded this part of northern Italy. An excellent video provides an overview of the period.

After bearing witness to local Nazi-era genocide, visiting Trieste’s two delightful castles—Duino and Miramare—will offer a welcome respite.

Marie Bonaparte, a member of the Duino family and an amateur photographer, was a disciple and friend of Freud as well as a supporter of Weiss. Displayed in Duino Castle (39-40-208-120), about 12 miles west of Trieste on the road to Monfalcone, are her portraits of Freud, said to be his best.

Bonaparte’s friend, the Prague-born poet and novelist Rainer Maria Rilke, stayed here. Visitors can enjoy the Rilke Path, a tree-shaded, mile-long cliff-top walk overlooking the sea, beginning behind the tourist information booth.

Castello di Miramare (39-40-224-143; www.castello-miramare.it) is also on the road to Monfalcone. Archduke Maximilian decided to build it here, in Grigniano, the bay where his boat took shelter in a storm in 1855. The stone castle still has its original furnishings. In the dressing room hangs a painting of Jerusalem by Maximillian’s wife, Charlotte. And in the second-floor dining room hangs the painting Jewess of Cairo by Jean-François Portaels.

Trieste’s best bargain is its tram, which creaks its way up the steep ascent from Piazza Oberdan, near the synagogue, then passes beautiful homes and vineyards as it whizzes to the mountaintop village of Opicina, where the Jewish community runs a summer camp and hosts Israeli children with disabilities. The views are spectacular, especially from the walk at Bertolini Woods, starting from the obelisk.

Another inexpensive and fun trip is the boat ride to Muggia, a former fishing village just south of Trieste that has an old town with narrow streets but also a museum of modern art. Boats leave from the Pescheria pier near the aquarium.

Side Trips
Gorizia, a divided city half in Slovenia and half in Italy, lies 22 miles northwest of Trieste in a verdant wine region. Domenis (www.domenis.com) is a local producer of kosher grappa and other kosher spirits.

Jews had an important role in this area, first as moneylenders and merchants and then, toward the end of the 18th century, as founders of a silk industry. Today, Gorizia barely has 10 Jews. In 1969, they formally joined the Trieste community and, in 1978, donated their synagogue to the city in exchange for its restoration. Today, it is the venue of Hebrew classes and meetings of the Friends of Israel Association (39-481-532-115); the synagogue also operates a small museum.

Originally, Jews lived on Via Rastello in a quarter called La Cocevia. When they were forced to live in a ghetto, they were moved to Via Ascoli. The synagogue, built in 1699 and expannded in 1756, is at No. 19. The street is named for Isaac Ascoli, a 19th-century Jewish linguist and philologist. A plaque marks his house.

Near the entrance of the yellow stucco synagogue is a plaque commemorating 45 Jews of Gorizia whom the Nazis deported to a concentration camp in a single night. Nearby is a memorial sculpture in the shape of a six-branched menora.

In the light-filled sanctuary, an elaborate floral iron grille surrounds the Ark, which is flanked by four dark pillars. Most interesting are the raised bima on the wall opposite the Ark and the dark wooden pews running the length of the sanctuary and facing the center, as in Romaniote synagogues.

The museum on the ground floor of the building has a permanent exhibition displaying various aspects of local Jewish history. It includes items related to the 88th Infantry division of the United States Army, the Blue Devils, which was stationed in the area between 1945 and 1947. Chaplain Captain Nathan A. Barack and other Jewish Blue Devils helped reestablish Gorizia’s Jewish community.

Outside, the iron gates ornamented with serpents, wreaths and garlands open on to an adjacent park; they were once the gates of the ghetto. (Contact Claudio Bulfoni for tours: 39-48-133-226; cell, 39-34-7019-0967.)

Aquileia, about 15 miles southwest of Gorizia, was the fourth largest city in the Roman Empire. Jews lived in Aquileia from Roman times and are said to have introduced Christianity there. The Patriarchal Basilica, declared a World Heritage Site by UNESCO, has a huge mosaic floor that includes scenes from the story of Jonah.

Books
In Svevo’s 1923 masterpiece Zeno’s Conscience: A Novel (Vintage, translated by William Weaver), set in Hapsburgian Trieste, the comic protagonist—an inveterate liar—keeps a journal on the suggestion of his psychoanalyst. He begins by recounting his many hilarious attempts to quit smoking.

Joseph Cary visited Trieste in search of the ghosts of Svevo, Saba and Joyce. A Ghost in Trieste (University of Chicago Press) is a memoir rich with the history, language, art and landscapes of the city and with excerpts from the three writers.

In 1943, thousands of European Jews crossed the Alps to seek refuge in Italy, not knowing that the Nazis would invade soon after. A Thread of Grace (Ballantine) by brilliant storyteller Mary Doria Russell is a historical novel set in Northern Italy that recounts how priests, nuns, villagers, partisans and local Jews hid the refugees until the end of the war.

Personalities
Legendary New York mayor Fiorello La Guardia had deep Jewish family roots in Trieste.His mother, Irene Luzzatto-Coen, was a descendant of the famous Luzzatto family of scholars, kabbalists and poets.

Rachel Morpurgo (1790-1891) was a Trieste-born Hebrew poet who sought to revive Hebrew poetry in Italy.

Recommendations
Alitalia flies visitors to Friuli Venezia Giulia airport near Trieste. Gabriella Kropf, of Key Jewish Tours (www.keyjewishtour.com), specializes in Jewish itineraries in Trieste and all of Italy. Annalisa Cadel (annalisa.cadel@libero.it) is a knowledgeable guide well versed in all things Jewish in Trieste.

Urban Hotel offers ultrachic accommodations in one of Trieste’s oldest quarters, a 15-minute walk from the synagogue (4 Androna Chiusa; www.urbanhotel.it). Le Corderie Hotel, a short bus ride from the city center, provides exceptional service and comfort (43 Via di Calvola; www.lecorderiehotel.it).

Trieste has no kosher restaurants, but kosher meals for the Sabbath can be arranged at the Jewish old age home (contact Key Jewish Tours). Kosher food products, including locally produced smoked turkey meat, are sold at the synagogue.

Kosher pastries are sold at La Perla (7c Via Santa Catarina), a nonkosher café, and kosher ice cream is available at two branches of La Siciliana (2 Capo di Piazza, off Piazza dell’ Unita, and 4C Viale XX Settembre).

The romance of great literature, the charming cafés, the beautiful vistas, the sparkling waters and, above all, the friendliness of the people, will make you fall in love with Trieste.