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Overview
Phoenicians, Greeks, Romans, Arabs, Normans, Spaniards, French, and Jews have all left their traces on “The Two Sicilies,” as mainland Naples and the island of Sicily were once known. Thanks to their position in the center of the Mediterranean, these two Sicilies have served as the meeting point of many civilizations. During the course of this unique trip, we will seek out these multicultural strands and study the rich and complex culture of this region and its Jewish communities.
We begin our travels in Naples, where Jews lived since the ancient Roman days of Pompeii and Herculaneum, both dramatically destroyed by an eruption of Mt. Vesuvius in the first century CE. In addition to visiting the remarkably preserved Herculaneum site and walking the ancient streets of Naples, we have the opportunity to meet with members of the local Jewish community.
Southwest of Naples, across the Tyrrhenian Sea, sits the island of Sicily. The center of Western civilization for centuries, Jewish communities once flourished there under a series of cosmopolitan and tolerant regimes that began with the Arab conquest of the island in the ninth century.
We fly into its capital of Palermo, exploring over the next days spectacular artifacts and cultural sites — from Roman mosaics to rare Jewish manuscripts, from an ancient Phoenician island settlement to the old Jewish quarter of Trapani. We move on to Agrigento, where we see some of the best-preserved ancient Greek ruins outside of Greece. We stay in Siracusa and visit the oldest mikveh (Jewish ritual bath) ever found in Europe as well as a spectacular Greek theatre still in use today. Our tour concludes in Taormina, where historical records from 1415 mention a modest Jewish community.
Scholar Moshe Ben Simon accompanies you on this tour, bringing to life the tantalizing past of Jewish life of the “Two Sicilies.” Along the way, you will stay at the best hotels, learn from local experts, and experience remarkable sites and spectacular scenery.
Highlights
11 nights of deluxe accommodations in Naples, Palermo, Agrigento, Siracusa, and Taormina
Discovery of the rich, multicultural history in Southern Italy, including Greek, Roman, Phoenician, and Jewish cultures
Ancient Jewish artifacts, including the oldest mikveh (ritual bath) in Europe and rare Jewish manuscripts
Visits to spectacular Greek and Roman ruins, including Herculaneum, Valley of Temples, and Neapolis
Shabbat dinners together and optional services with local Jewish communities
Walking tours of the oldest neighborhoods of Naples and the Giudecca (ancient Jewish quarter) of Siracusa’s Ortigia island
Travel by boat to the uninhabited Mozia Island, an ancient Phoenician trading post and a window into Sicily’s Phoenician past
Itinerary
Friday, October 30 | Naples
Arrive in Naples and check in to the deluxe Grand Hotel Santa Lucia, one of Naples’ finest hotels. Rest and relax.
We gather in the evening for a tour overview by our accompanying scholar, followed by an orientation and opportunity to get to know one another. A festive Shabbat dinner at our hotel is included.
Meals: Dinner
Accommodations: Grand Hotel Santa Lucia
Saturday, October 31 | Naples
This morning includes free time to explore Naples on your own or attend services with the local Jewish community.
Discover “Spaccanapoli” in the afternoon on an optional walking tour. Literally “Naples splitter,” this succession of streets divides Naples’ historic district into two halves. We explore the old part of town, dating back to Greek and Roman times and still considered the heart of the city. It contains some of Naples’ most interesting artistic and cultural highlights, including churches, picturesque shops, and traditional artisans.
We are then treated to a lecture by our scholar, followed by dinner on your own.
Meals: Breakfast
Accommodations: Grand Hotel Santa Lucia
Sunday, November 1 | Naples | Palermo
Our day begins with a guided visit to what was once the Roman city of Herculaneum. Now a UNESCO World Heritage site, the remarkably preserved city existed at the same time as Pompeii and was known for its luxurious villas and affluent residents. The eruption of Vesuvius in 79 AD buried Herculaneum under approximately 16 meters of volcanic material, preserving buildings, frescoes, mosaics, and even organic materials like food and furniture.
After lunch, we depart for the airport and take a late afternoon flight to Palermo, where we check in to the Grand Hotel et des Palmes and have time to relax.
Palermo has a rich Jewish history, with a community present since the 6th century. The Jewish quarter, known as the Giudecca, was a vibrant part of the city’s cultural fabric until the expulsion in 1492. In recent years, there have been efforts to revive Jewish heritage in Palermo.
Dinner is on your own in Palermo.
Meals: Breakfast, lunch
Accommodations: Grand Hotel et des Palmes
Monday, November 2 | Palermo
We start the day at Monreale, a city with a magnificent twelfth-century basilica which has renowned mosaics that recount stories from the Old and New Testaments. After lunch on your own, we visit the Regional Library, where we have the opportunity to view rare Jewish manuscripts.
In the evening, our scholar will give a talk, followed by dinner together.
Meals: Breakfast, dinner
Accommodations: Grand Hotel et des Palmes
Tuesday, November 3 | Palermo
Today we tour Mozia, an ancient Phoenician island settlement in the 8th century BC. Accessible by a 15-minute boat ride across a lagoon, Mozia and its remarkable archaeological museum provide visitors with a rare, unspoiled glimpse into Sicily’s Phoenician past.
We then visit Trapani, an historical port city with stunning coastal scenery, where we have lunch and walk through what was once the Jewish quarter or Giudecca.
We return to Palermo in time for dinner on your own.
Meals: Breakfast, lunch
Accommodations: Grand Hotel et des Palmes
Wednesday, November 4 | Palermo | Agrigento
This morning, we visit the Steri Palace Museum, an iconic historical and architectural landmark containing seven centuries of history. We also attend a traditional Sicilian marionette show at the Opera dei Pupi (Puppet Theater), which is inscribed on UNESCO’s Representative List of the Intangible Cultural Heritage of Humanity.
We then depart Palermo for Agrigento, with lunch on your own en route. Upon arrival, we check in to the deluxe Villa Athena Hotel, located within the UNESCO World Heritage-listed Valley of the Temples. There is time to rest and enjoy the spectacular scenery before dinner at the hotel.
Meals: Breakfast, dinner
Accommodations: Villa Athena
Thursday, November 5 | Agrigento
We begin the day with a visit to the Valley of the Temples on a walking tour that introduces us to one of the most important archaeological sites in the world. Valley of the Temples was founded in the 6th century BCE as the Greek colony of Akragas, and became one of the most powerful and prosperous cities in the Mediterranean. Today the site showcases some of the best-preserved ancient Greek ruins outside of Greece.
After lunch, we take a private, guided tour of the Regional Archaeological Museum “Pietro Griffo,” in Agrigento, one of the most important and most visited archaeological museums in Sicily. This museum displays more than 5,600 artifacts arranged both in chronological and topographical order, illustrating the history of the Agrigentan territory from prehistoric times to the end of the Greek-Roman period and offering a deeper understanding of the ancient Greek and Roman civilizations that once thrived in Sicily.
In the evening, we enjoy a lecture by our scholar and dinner at the Villa Athena.
Meals: Breakfast, lunch, dinner
Accommodations: Villa Athena
Friday, November 6 | Agrigento | Siracusa
After breakfast, we depart Agrigento for Siracusa. En route, we tour the Villa del Casale, an estate that dates to the fourth century CE. The villa is renowned for what many consider the most exceptional Roman mosaics in the world. We stop for lunch together in the medieval town of Piazza Armerina.
In Siracusa, we check in to the Grand Hotel Ortigia to rest and relax before a festive Shabbat dinner at our hotel.
Originally a Greek colony, Siracusa was founded in the eighth century BCE and described by Cicero as “the greatest Greek city and the most beautiful of all.” It now has one of the largest concentrations of Greek ruins outside of Greece.
Meals: Breakfast, lunch, dinner
Accommodations: Grand Hotel Ortigia
Saturday, November 7 | Siracusa
Take the morning to rest and relax — or take an optional morning walking tour of the charming Siracusa island of Ortigia, considered the historical heart of the city. Ortigia’s Jewish heritage traces back over two millennia. In addition to the ancient market and Roman ruins, we walk the narrow, winding streets of the Giudecca (ancient Jewish quarter). At its peak, the Jewish population in Syracuse numbered between 1,000 and 3,000, making up a significant portion of the city’s inhabitants. Here, we visit an ancient mikveh (Jewish ritual bath) fed by natural spring water and only discovered in 1989. Located 59 feet below ground level and dating back to the 6th century, it is one of the oldest ever found in Europe. At the Bellomo Gallery, we view tombstones from the Jewish medieval cemetery that are on display.
The afternoon is free for you to rest and relax or explore.
We then gather for a lecture by our scholar, followed by dinner on your own.
Meals: Breakfast
Accommodations: Grand Hotel Ortigia
Sunday, November 8 | Siracusa | Taormina
Today we travel to Taormina, stopping first to tour Siracusa’s World Heritage archaeological site, including the archaeological park of the Neapolis. Here, we will visit the monolithic Greek theater; its cavea (curved, stone seating area), one of the largest ever built by the ancient Greeks, is still used today for classical performances. We also visit the landmarks of the Altar of Hieron II, used for large-scale ceremonies; the “Ear of Dionysius,” a large limestone cave famous for its acoustics; and an ancient Roman amphitheater. We’ll have lunch afterwards, en route to Taormina.
Upon arrival in Taormina, we check in to the five-star Grand Hotel San Pietro, one of the finest in Taormina, with breathtaking views of the sea. Enjoy dinner on your own.
Meals: Breakfast
Accommodations: Grand Hotel San Pietro
Monday, November 9 | Taormina
This morning, we take a walking tour of picturesque Taormina that includes the town’s former Jewish quarter, as well as its magnificent Greek theater, an incredibly well-preserved 3rd-century BCE amphitheater with stunning views of the sea and Mount Etna.
The afternoon is free to rest, relax, or further explore the charms of Taormina on your own.
This evening we gather for a final dinner together and farewells.
Meals: Breakfast, dinner
Accommodations: Grand Hotel San Pietro
Tuesday, November 10 Taormina | Catania
Individual departures for Catania Airport and your return flights to the U.S.
Meals: breakfast
Gallery
Traveling with you…
Each of our scholars are outstanding experts in their fields and play an active role in helping us design our journeys as well as accompanying us as we travel.
Moshe Ben Simon
Moshe Ben Simon was born and raised in Tel Aviv-Israel, in a Sephardic Jewish family. After his military service in the Israeli army, Moshe moved to Sicily where he studied Literature and Philosophy and earned a B.A. from the University of Messina with his final thesis, “Inquisition and ‘Jewish Herecy’ in Sicily in the Period Between Ferdinand the Catholic and Charles V.” For the past 25 years, he has worked and lived in Sicily as a tour guide, specializing in the Jewish history of the island. Moshe has guided and lectured for three previous tours for Jewish Heritage Travel — all to great acclaim. He is also the author of numerous articles related to Judaism and Jewish history of Sicily, including, among others, “La Presenza Ebraica in Sicilia : Fra Memoria ed Oblio” (“The Jewish Presence in Sicily: Between Memory and Oblivion”).
Lucy Rapoport
Lucy Rapoport, trip leader, has guided and accompanied many previous Jewish heritage tours, all to great acclaim. Born and schooled in England before moving to Italy as a young adult, Lucy is fluent in Italian, German, French, and Spanish and has been a tour manager for over twenty years. Specializing in Europe, she has accompanied previous Jewish groups to such places as Lithuania, Krakow, Prague, Berlin, Croatia, Spain, Romania, Serbia, France, northern and southern Italy, and Sicily. With Lucy’s attention to detail, knowledge of history, and considerable expertise in guiding groups, participants will be well served on this trip.
Accommodations
Grand Hotel Santa Lucia, Naples
The stylish Grand Hotel Santa Lucia brings to life the Neapolitan Belle Epoque. Featuring panoramic views of the entire bay of Naples and Mt. Vesuvius, this seafront hotel provides comfort and tranquility and a full array of modern amenities, including toiletries, bathrobe and slippers, as well as WiFi. In addition to a restaurant serving breakfast, guests are invited to enjoy the hotel’s classic bar and the on-site gym.
Grand Hotel et des Palmes, Palermo
In the vibrant heart of Palermo, the luxurious, five-star Grand Hotel et Des Palmes exudes timeless elegance and a commitment to unforgettable hospitality. Located in the former residence of Ingham-Whitaker family, the hotel features a majestic lobby, exquisite architectural detail, and refined furnishings. The charming rooms provide calm, comfort, and beauty, while its restaurants celebrate Sicilian culinary tradition with a touch of contemporary innovation.
Villa Athena, Agrigento
The Villa Athena, located in the heart of the Valley of the Temples, overlooks the Temple of Concordia, a fine example of architectural beauty dating back to the fifth century BCE. Formerly a princely residence of the eighteenth century, the building was carefully restored to preserve its architectural style; thus was born the five-star Villa Athena, surrounded by a beautiful park of Saracen olive trees and palms, making it a quiet and comfortable location.
Grand Hotel Ortigia, Siracusa
The five-star Grand Hotel Ortigia is situated in a recently renovated historic building on the island of Ortigia, in Siracusa, just a few steps from the old town center, Fonte Aretusa, and Marina di Siracusa. The hotel offers a restaurant with a panoramic sea-view terrace, as well as welcoming guest rooms. Enjoy a memorable stay in one of the most beautiful towns of Sicily.
Grand Hotel San Pietro, Taormina
Suspended between sky and sea, the Grand Hotel San Pietro offers an unparalleled panoramic view of the Ionian Sea, surrounded by a lush Mediterranean garden of citrus and ancient olive trees. A finely restored early 1900s villa, the hotel stands out for its timeless elegance and modern Sicilian-style design with colorful contemporary touches. The rooms, pool, restaurants, gym, and spa combine to provide an unforgettable Sicilian experience.
Details
Program Cost: $9,995* includes:
- 1 nights’ accommodations at deluxe hotels
- Full breakfast daily; five lunches; six dinners
- All group transportation via deluxe air-conditioned coach
- All lectures, guided tours, museums, and site entrance fees
*Per person, double occupancy; single supplement: $3,750. Fees not included: gratuities: $275.
Travel note: Plan to arrive in Napoli, Italy (NAP) on October 30, 2026 and depart from Catania Airport (CTA) on November 10, 2026.
Secure your place
Book Now: use the link below to reach our easy online booking form.
By phone: 845-256-0197 Monday–Friday, 10am–4pm EST.
Payment Reserve your space with a nonrefundable deposit of $1,000 per person. Final balance is due 120 days prior to departure.
Membership Participation on these tours is a benefit for active members of our museum partners. During the registration process, you will be asked about your membership status with your affiliated museum. If you are not a current member, you will have a chance to activate your membership.
Participation Tour sizes are limited to 28 participants unless otherwise noted. Trips entail considerable walking including over uneven terrain. Participants need to be in good health, be able to keep up with the group, be able to experience group and cultural differences with grace. Please let us know if you have any physical conditions that may require special attention while on tour. For more information please see our FAQ page.
Cancellations All cancellations must be received by Jewish Heritage Travel in writing. Cancellations received 120 days or more prior to departure: full refund less nonrefundable deposits, per person; 119–90 days prior to departure: 50% refund per person after nonrefundable deposits. 89–0 days before departure: no refund.
Trip Cancellation Insurance Jewish Heritage Travel strongly urges all participants to purchase travel insurance for coverage of losses necessitated by having to cancel due to illness or accident. For your convenience, we are providing a link to Allianz Global Assistance, which many past participants have used. Please use code ACCAM/Agency ID# F026815 or feel free to use your own insurance agent. When purchasing insurance, please consider the plans carefully to familiarize yourself with what is covered. In this context, do take note that most insurance companies generally will waive exclusion for preexisting conditions only if your application is received by them within 14 days from the date of your program registration. If you have a preexisting medical condition and are interested in taking trip insurance, you should do so either with Allianz or through your own insurance agent within 14 days of registration.
Changes All rights are reserved by Jewish Heritage Travel to make scholar substitutions and/or to modify the itinerary (including hotels) as needed. Every reasonable effort will be made to operate the program as planned; however, should unforeseen world events and conditions require the itinerary to be altered, Jewish Heritage Travel reserves the right to do so for the safety and best interest of the group. Any extra expenses incurred in this situation are the responsibility of the participant.
Disclaimer of Responsibility By registering for this program, participant specifically waives any and all claims of action against Jewish Heritage Travel and our museum partners listed below and their respective staffs for damages, loss, injury, accident, or death incurred by any person in connection with this tour. Jewish Heritage Travel and our museum partners listed below and their respective staffs assume no responsibility or liability in connection with the service of any train, vessel, carriage, aircraft, or other conveyance that may be used wholly or in part in the performance of their duty to the passengers. Neither will the Jewish Heritage Travel and our museum partners listed below or their staffs be responsible for any injury, death, loss, accident, delay, or irregularity through neglect or default of any company or person engaged in carrying out the purposes for which tickets, vouchers, or coupons are issued. Any personal activities arranged outside the Jewish Heritage Travel published tour itinerary are solely and wholly the responsibility of the individual traveller whether or not a representative of Jewish Heritage Travel has provided any guidance. No responsibility is accepted for losses or expenses due to sickness, viruses, weather, strikes, wars, and other causes. In the event it becomes necessary or advisable for any reason whatsoever to alter the itinerary or arrangements, including hotels or scholars, such alterations may be made without penalty. All rights reserved to require any participant to withdraw from the tour at his/her own expense when such an action is determined by the tour staff to be in the best interest of the participant’s health and safety and that of the group in general. Prices subject to change. Cost in effect at time of registration will be honored.
