The Two Sicilies
Naples & Sicily
The Best of Southern Italy
October 27–November 7, 2023


Phoenicians, Greeks, Romans, Arabs, Normans, Spaniards, French, and Jews have all left their traces on “The Two Sicilies,” as Naples and Sicily were once known. Thanks to their position in the center of the Mediterranean, these two Sicilies were the meeting point of many civilizations. During the course of this unique trip, we will seek out those traces and study the rich and complex culture of this region and its Jewish communities.

Jews have had a presence in Naples since the days of Pompeii and Herculaneum, both dramatically destroyed by an eruption of Mt. Vesuvius in the first century CE. A stone’s throw away, across the Strait of Messina, stands Sicily — only a short distance from Africa. Like Naples, it too has a volcano, Mt. Etna, with a destructive past. Here, Jewish communities once flourished under a series of cosmopolitan and tolerant regimes that began with the Arab conquest of the island in the ninth century and continued through the period of Norman control, until they came under the same edict of expulsion that ended Jewish life in Spain in 1492.

For centuries, Sicily was truly the center of civilized life; it still contains impressive remains of antiquity in the form of Greek theaters and Roman temples and shows the influence of all the peoples who have ever lived there. Join scholar Moshe Ben Simon and local experts on this special trip to Sicily and experience startling sights, spectacular scenery, delicious foods, and friendly people.

Along the way, we will stay at the best hotels and learn about the tantalizing past of Jewish life of the “Two Sicilies.”



  • 11 nights of deluxe accommodations in Naples, Palermo, Agrigento, Siracusa, and Taormina

  • Visit the golden mosaics of the Monreale Cathedral, the Jewish manuscripts of the Regional Library, Villa del Casale with the world’s most exceptional Roman mosaics, the Greek ruins of Siracusa (including an ancient mikveh), the monolithic Greek theater at the archaeological park of the Neapolis, castle “La Zisa,” the Tapestry Museum, and the Steri Palace Museum.

  • Walking tours: Spacca Napoli, the Valley of the Temples, the island of Ortigia, Taormina; Guided tours: the Archaeological Park of Herculaneum and the Regional Archaeological Museum

  • Performance: The traditional Sicilian marionette theater (Opera dei Pupi, part of UNESCO’s Intangible Cultural Heritage of Humanity list)

  • A boat ride to the uninhabited Mozia Island, an ancient Phoenician trading post and window into Sicily’s Phoenician past


Friday, October 27 | Naples

Arrive Naples and check in to the deluxe Grand Hotel Vesuvio, one of Naples’ finest. Rest and relax.

Evening: Overview by our accompanying scholar. This will be followed by an orientation meeting and an opportunity to get to know one another. A festive Shabbat dinner at our hotel is included.

Saturday, October 28 | Naples

Morning: Free time to explore Naples on our own or attend services with the local Jewish community.

Afternoon: (optional) Walking tour of Spacca Napoli, the succession of streets that divide Naples’ historic district into two halves. The oldest part of town, dating back to Greek and Roman times and still considered the heart of the city today, contains some of Naples’ most interesting artistic and cultural highlights, including churches, picturesque small shops, and traditional crafts makers. Villa Pignatelli, the early-nineteenth-century home of Carl Mayer Rothschild, will be included in the tour.

Evening: Lecture by scholar followed by dinner on our own.

Sunday, October 29 | Naples | Palermo

Our day will begin with a guided visit to Herculaneum, a UNESCO World Heritage site – a wealthier town than Pompeii, possessing an extraordinary density of fine houses with far more lavish use of colored marble cladding. Following lunch, depart for the airport and late afternoon flight to Palermo. Check in to the Villa Igiea, a five-star deluxe hotel in Palermo.

Monday, October 30 | Palermo

Visit Monreale, the magnificent twelfth-century basilica, with its amazing interior recounting the Old Testament. After lunch visit the Regional Library to view Jewish manuscripts. Then tour the Norman castle “La Zisa.”

Evening: Lecture by scholar and dinner (included).

Tuesday, October 31 | Palermo

Tour Mozia, an ancient Phoenician island settlement, accessible by a 15-minute boat ride across a lagoon and past salt flats still harvested in the ancient method. The Mozia Archaeological Museum is a remarkable museum as well as the ruins of an equally remarkable civilization. Mozia provides visitors with a rare, unspoiled glimpse into Sicily’s Phoenician past.

Lunch in Marsala (included) and a visit to the Tapestry Museum, with eight precious sixteenth-century Flemish tapestries depicting scenes from the Roman-Jewish war (first century CE) that are attributed to the Spanish-Flemish painter Pedro Campaña.

Return to Palermo in time for dinner on our own.

Wednesday, November 1 | Palermo | Agrigento

Depart Palermo for Agrigento. Visit Steri Palace Museum and attend a performance of the Opera dei Pupi (Puppet Theater) followed by lunch on own en route. Check in to the deluxe Villa Athena Hotel, with time to rest and enjoy the spectacular scenery surrounding the Villa Athena. Dinner at our hotel (included).

Thursday, November 2 | Agrigento

Begin the day with a private, guided tour of the Regional Archaeological Museum “Pietro Griffo,” 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. It will be the perfect introduction to our visit to the Valley of the Temples this afternoon. After lunch (included) a walking tour of the Valley of the Temples, introduces one of the most important archaeological sites in the world as well as a UNESCO World Heritage site.

Lecture by scholar and dinner at the Villa Athena (included).

Friday, November 3 | Agrigento | Siracusa

Depart Agrigento for Siracusa. En route tour Villa del Casale, an estate that dates to the third century CE. The villa is renowned for what many consider the most exceptional Roman mosaics in the world. Have lunch in Piazza Armerina (included). Originally a Greek colony, Siracusa—founded in the eighth century BCE and described by Cicero as “the greatest Greek city and the most beautiful of all”—has one of the largest concentrations of Greek ruins outside Greece. Check in to the Grand Hotel Ortigia, and rest and relax before a festive Shabbat dinner at our hotel (included).

Saturday, November 4 | Siracusa

Free to rest and relax or take an optional morning walking tour of the island of Ortigia, where we will visit the ancient market and Roman ruins; and walk the narrow streets of the Giudecca (ancient Jewish quarter) and see what was once the site of a synagogue and ancient mikveh (Jewish ritual bath). Located 11 meters below ground level, this mikveh is among the oldest ever found in Europe. At the Bellomo Gallery some tombstones from the Jewish medieval cemetery are displayed.

Afternoon: Free…..

Evening: Lecture by scholar followed by dinner on our own.

Sunday, November 5 | Siracusa | Taormina

Depart Ortigia for Taormina, with a stop 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. Our morning tour will continue with a visit to the sacrificial Altar of Hieron II, “Ear of Dionysius” (an artificial limestone quarry so named by the painter Caravaggio), and its ancient Roman amphitheater before we continue to Taormina. Upon arrival in Taormina, check in to the five-star San Domenico Hotel, one of the finest in Taormina, with an expansive view of the sea. Lunch and dinner on our own.

Monday, November 6 | Taormina

A walking tour of Taormina includes its magnificent Greek theater. This afternoon is free to rest, relax, or explore Taormina on our own,

Evening: Gather for closing thoughts by Lecturer followed by a final dinner together (included).

Tuesday, November 7 Taormina | Catania

Depart Taormina for Catania airport and return flights to the U.S.

Please Note: Daily schedule may be modified subject to weather or unanticipated changes.

Traveling with you…

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”).


Grand Hotel Vesuvio, Naples
Attention to detail is the five-star Grand Hotel Vesuvio’s theme, while graciously combining old-world charm with modern comfort and the latest technology. Dining at the Caruso Roof Garden Restaurant is a unique experience, and there is a breathtaking view of the bay. The Grand Hotel Vesuvio is only a few steps from the Royal Palace and the Castel dell’Ovo.

Hotel Villa Igiea, Palermo
Located at the foot of Mount Pellegrino, overlooking the Gulf of Palermo, the Grand Hotel Villa Igiea is a five-star luxury hotel in Art Nouveau style. With an old-world, romantic atmosphere of the Belle Epoque, the Villa Igiea has welcomed guests for over a century. It is surrounded with colorful terraced gardens and the scent of jasmine and Mediterranean herbs.

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.

San Domenico Palace Hotel, Taormina
Carved into a rocky hillside in Taormina, Sicily, the five-star San Domenico Palace Hotel commands a stunning perch on the coast. There are multiple terraces, four restaurants, fragrant gardens, and a swimming-pool area, all featuring vistas of the glittering Ionian Sea. The hotel, housed in a former fourteenth-century monastery, retains its classic façade and soaring ceilings with spacious, elegant, light-filled rooms.


Program Cost:

Program cost: $6,950* includes:

  • 11 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: $1,950. These prices are valid for reservations made before December 1, 2022. Fees not included: gratuities: $165; On-tour group flight from Naples to Palermo: approximately $185. Museum of Jewish Heritage membership for nonmembers: $54.

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.

Participation Tour sizes are limited to 30 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, and be fully vaccinated against COVID-19. Please let us know if you have any physical conditions that may require special attention while on tour.

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, each participant specifically waives any and all claims of action against any participating organization and the Jewish Heritage Travel office and their respective staffs for damages, loss, injury, accident, or death incurred by any person in connection with this tour. Any participating organization and the Jewish Heritage Travel office 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 any participating organization or the Jewish Heritage Travel office 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. 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.