Jewish Cultural Tour of Sicily: History & Legacy

A 10 day trip to Italy 
4.92 out of 5 stars
12 reviews

The finer details of Jewish tradition have left a tangible mark on Sicily, adorning ancient buildings and shaping local culture. A hidden mikveh (bath used for ritual immersion) continues to bubble with fresh spring water. Stars of David decorate municipal buildings in towns that have not had a Jewish community for centuries. Synagogue foundations and demarcations of Jewish Quarters are found throughout the region. Jewish culture and traditions are as spirited and as tenacious as the people who hold these values dear. Your Jewish cultural tour of Sicily highlights the influence of Sicily’s Jewish population in the art, architecture, and cuisine on a luxury excursion of a unique and untold history.  

Customize This Trip For Me
Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Palermo, Monreale, Agrigento, Valley of the Temples, Noto, Syracuse, Taormina, Catania, Sciacca, Segesta, Erice, Villa Romana del Casale, Mount Etna, Messina

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Legacies of Palermo

Palermo is a city that encompasses history, combining its past and present in the   ancient architecture and energetic markets. The Mediterranean Sea brushes against the edges of the city at the 9th-century port. The people are friendly and eager to speak with visitors from around the world. Your private transfer meets you at Falcone-Borsellino Airport upon your arrival. Elements of Jewish life on the island can be traced back almost two millennia ago. Palermo’s community thrived in the 15th century. Your private transfer escorts you to your hotel in the heart of the city.

The mixture of architectural styles paints an elaborate portrait of Palermo’s past and the Island’s history, having been claimed by invaders from Carthage and Spain. The city is a melting pot of history, as shown in the Norman architecture of the Palazzo dei Normanni, and the Arab influence in the cuisine at the Ballarò Street Market. Quattro Canti, a circular space erected in the 17th century, has a Baroque elegance. Three-story facades have niches decorated with lavish neoclassical sculptures framed with Greek columns. The statues symbolize the four seasons. Female patron saints adorn the uppermost floor and grace the square with good fortune and protection.

What’s Included: transfer, accommodation

Day 2: The Root of Jewish Culture in Palermo

In the morning, the jovial calls of the market echo along the cobblestone streets. Vendors display vibrant fruit, from strawberries to pomegranates. The sun shines over the Norman Palace, setting the historic stones alight with a golden glow. Your guide meets you in the hotel lobby after breakfast. You are eager to set out into the city and explore what remains of the Jewish culture and peoples that once called Palermo home. Consider reading some of our travelers' Sicily travel reviews to gain additional ideas to add to your Sicily vacation. The Palermo Cathedral combines the Norman Façade with elements of Arab influence, along with an interior of Byzantine gilded mosaics. The eclectic architectural elements provide insight into the combination of societies that have contributed to the current culture of the city.

Your guide leads you to La Giudecca, the Jewish quarter of Palermo. Unlike Jewish neighborhoods around Europe, La Giudecca was an open quarter where Jewish families settled to be closer to the synagogue and the community. The Great Synagogue once stood at the center of the Jewish quarter. The structure was turned into the monastery of St. Nicolo Tolentino in the 17th century, but contains elements of the temple ruins. The streets around the neighborhood are labeled in Italian, Hebrew, and Arabic. In 2011, a rabbi held the first bar mitzvah in Palermo in approximately 500 years.

What’s Included: breakfast, tour, accommodation

Day 3: Images of the Ancient and Medieval Times

In the morning, the aroma of rich espresso drifts from the cafes along the main streets of the city. Bright orange rinds shimmer in the marketplace. The scent of fried arancini, a succulent fried rice ball coated in breadcrumbs, overtakes the scent of the produce. After breakfast, your guide leads you away from the traditions of Palermo and to the ancient wonders of Segesta. A Greek temple stands atop a hill overlooking the rolling green countryside sweeping out to the sea. The Doric temple was erected in the 5th century BC and contains 36 columns. The Mediterranean landscape undulates between lush trees and pebbled hillsides.

You can see the shimmering indigo of the sea in the distance. You continue to Erice, a medieval town located on the Eryx mountaintop at 2,463 feet above sea level. Cobblestone streets line the triangular summit. The Arabs built Pepoli Castle. The Normans erected Venus Castle in the 12th century. Both cast imposing towers that look over the foothills, offering unforgettable views of the island scenery, including the crashing waves of the Mediterranean Sea. Venus Castle was named because it was constructed over the ancient Temple of Venus.

What’s Included: breakfast, lunch, tour, transfer, accommodation

Day 4: Wine Culture

The sea breeze rustles the palm fronds. Sunlight bathes the esplanade of the southern seaside city of Sciacca. The thermal springs of the city were coveted by various civilizations, including the Greeks who settled in the area in the 7th century BC. The modern city layers the hillside with a charming fishing harbor complementing the shoreline. The town’s castle and old city walls line the upper layers of the hill. After breakfast, your guide meets you at the hotel and takes you to a vineyard and winery located outside of Sciacca.

The rolling hills along the Mediterranean turn to a lush valley blanketed with vines. The vineyard encompasses nearly 300 acres. Your private guide leads you along the rows of vines explaining how the variations of the soil affect the grapes. The earthen aroma drifts over the expanse. Wine has always played a unique role in Jewish customs, used for blessing and in celebration of the cycle of life. It is meant to inspire, comfort, raise spiritual awareness, and even lend dignity to an occasion.

Learning the process of winemaking on a traditional family winery brings a deeper connection to the drink and its importance in Jewish and Sicilian heritage. You enter the library, surrounded by hundreds of books. The scholarly ambiance adds a formal layer to your tasting. Your guide explains the variety of samples you are about to taste. The Burdese has splendid notes of spices, red fruit, and cocoa. The full body is elegant and harmonious.   

What’s Included: breakfast, tour, accommodation

Day 5: View from the Past

The quarters of the medieval design of Sciacca continue to segment the city. The avenue Corso Vittorio Emanuele runs through the city center, intersecting the layers of the various neighborhoods. In the morning, the view from Piazza Scandalito is exceptional. The dramatic façade of Palazzo Steripinto borders the square. A stairway leads to the harbor below. Colorful fishing boats wade in the water. Fishermen carry their catch to the market. The fresh scent of the sea blends with the aroma of citrus. After breakfast, your guide takes you away from Sciacca for the day and leads you to the ancient edges of the modern city of Agrigento. The Valley of the Temples is an archeological park peppered with ancient Greek ruins.

Wild olive and orange orchards flourish along the rolling hills. The park encompasses more than 3,212 acres. The city expanded heavily in the 5th century and traces of the encircling defensive walls can still be seen. The most impressive feature is the Temple of Concordia, one of the best-preserved ancient Greek temples in Italy. The Doric structure was erected in the 5th century and has remained well preserved due to its transformation into a Christian basilica in the 18th century, when the main structure was reinforced. The ancient civilization thrives in the imagination, showing one way a culture can persist through time.  

What’s Included: breakfast, tour, accommodation

Day 6: Allure of Medieval Stone

The Cathedral of Sciacca was erected in the 12th century. Three of the original apses erected by the Normans survive today. The marble statues on the Baroque façade glint in the sunlight. After breakfast, you say goodbye to Sciacca and make your way to Agira. An Iron Age tribe settled the ancient city and it eventually grew to a Greek colony boasting a population of over 10,000 people. Norman churches and elements of the Arab-Byzantine fortress decorate a cityscape now known as the fashion village, due to its unique boutique stores and connection to the factory outlets of Southern Italy.

Your guide leads you through the bustling streets of the city, leading you to Chiesa di San Salvatore. The interior houses a miter decorated with precious stones from the Middle Ages. Your guide points out the Aron Hakodesh, the Holy Ark, located inside the church. The ark was left behind when the Jewish citizens of the island were expelled in the 16th century. Hebrew inscriptions decorate the façade of the ark. The artifact lends insight into the Jewish community of medieval Sicily. The historic stone structure is captivating.

What’s Included: breakfast, lunch, tour, transfer, accommodation

Day 7: View to a Different World

Syracuse is a city surrounded by ancient history and stunning mythology, encapsulating a timeless allure. The city streets continue to bustle. Syracuse was once the largest city in antiquity with a population greater than even Athens at the height of the city-state’s power. The scent of the nearby citrus orchards drifts through the streets in the breeze. Locals sit at café tables in elegant piazzas surrounded by Baroque palaces. Cobblestone streets lead down to the sparkling Mediterranean coastline. Your guide leads you on a fabulous historical tour of the city, taking in the ancient and medieval wonders, along with a unique look into the Jewish heritage hidden underneath the city streets.

The island of Ortygia is an ancient district of Syracuse filled with limestone palaces and elaborate churches. The mikveh of the old Jewish neighborhood of La Giudecca dates back to the 15th century and is considered the oldest mikveh to have survived in Europe. The ritual baths were carved into the underground limestone chamber more than 65 feet below ground. An ancient spring provided endless clean and flowing water to the five immersion pools. The limestone and the pool’s depth keep the chamber at a cool, refreshing climate.  

What’s Included: breakfast, tour, accommodation

Day 8: In the Shadow of Etna’s Peak

In the morning, the bright city of Noto shines in the sunlight. The buildings contain a red and golden glow. Corso Vittorio Emanuele has elegant manicured walkways lined with opulent baroque palaces and graceful churches. After breakfast, you leave the charms of Noto behind and venture to the city of Catania on the shores of the Ionian Sea. Mount Etna rises over the cityscape, creating a dramatic backdrop. The city was rebuilt in the 17th century after a series of natural disasters left the ancient foundations devastated. Today, the city boasts an enchanting Baroque style with large squares and wide avenues fit for royalty.

Your guide points to the unique gray coloring of certain buildings. The hue stems from the material used in the construction, having been molded and structured from lava. The fish market thrives near Piazza Duomo, filled with vendors promoting the fresh seafood caught earlier that morning. The Cathedral of Saint Agatha has an impressive marble façade with columns embellishing the structure, each one taken from the Roman amphitheater. In the subterranean levels of the church, your guide points out the Roman baths. When you step onto Via Etnea, you have a clear view of the looming mountain peak in the sky.

What’s Included: breakfast, tour, transfer, accommodation

Day 9: Life and Times in Messina

Messina is a modern city wrapped in an exterior of its past. The natural harbor looks out into the Strait of Messina where people can gaze upon mainland Italy. The people are friendly and energetic. Music fills the streets and color radiates from the buildings. The city once held the highest court of appeal for all Jews in Sicily, and maintained one of the largest Jewish communities in Sicily during the Middle Ages. Your guide leads you along Via Cardines, which was once Via della Giudecca, traveling through the heart of the Jewish Quarter.

At the Palazzo Penso, you look up to find Stars of David shaped into the iron grates of the balcony. Small details of the vibrant Jewish community continue to decorate Messina. Outside of the city, three archways half filled with rocks are the remaining ruins of the Savoca Synagogue, which set the foundation for the Church of Saint Michael at the top of the hill. The quiet remains of the historic synagogue have withstood the test of time; people from around the world continue to acknowledge its place in Sicilian history.   

What’s Included: breakfast, tour, accommodation

Day 10: Reshaping the Ruins 

Taormina is a city on the cliffs overlooking the stunning Mediterranean Sea. The water shifts from turquoise to indigo before curling against the rocky base of the precipice. Cobblestone streets meander along the hillside. Locals enjoy a rich cup of espresso in the shaded piazzas. On the edge of town is the Greco-Roman Theater, providing a view of Mount Etna in the distance. Before your private transfer meets you at your hotel and escorts you to Catania-Fontanarossa Airport, you explore Taormina once more. The elements of the wealth of Jewish history in the city are present but understated.

A street sign informs people that they have entered the Jewish neighborhood. Stars of David adorn the Municipal Building in the former Jewish quarter. In the 17th and 18th centuries, the Sicilian government invited the Jewish population that was once expelled by Spanish rule to return to the island. The sun casts a light over the various buildings adorned with Stars of David, further adding another layer of perseverance to the standing Jewish-Italian culture.

What’s Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.