Southern Italy & Sicily
- May 19-30, 2023
- Starting from $4599
- For Jewish Singles

The hidden treasures of Southern Italy and Sicily are yours to explore for it’s here you’ll find breathtaking scenery, historic cities, centuries-old hilltop villages and iconic cuisine.
Join us as we journey along the crossroads of civilization in Sicily and on to the spectacular coastlines of Southern Italy. Discover Jewish Palermo and uncover Sicily’s Moorish and Norman influences that intertwine with Greek and Roman ruins standing guard over the landscape. Explore Agrigento’s ancient Valley of the Temples and take in the beautiful, historic hilltop town of Taormina. Visit a local winery to learn about the wine-making process, enjoy a wine tasting and dinner featuring regional specialties. Then, explore the ancient town of “Sassi di Matera,” known for its cave dwellings, and spend time in the mystical town of Alberobello with its unusual cone-shaped roofed homes known as “trulli.” Discover spectacular Mt. Etna Volcano National Park, and take in Sorrento and the Amalfi Coast with some of the most stunning panoramic views in the world. In evocative Pompeii, walk in the footsteps of ancient Romans who perished in the foothills of Mount Vesuvius. We end our tour in the Eternal City of Rome where we’ll tour the Vatican through the Jewish lens, and you’ll have time to explore the piazzas, trattorias, and beautiful architectural styles of Rome.
Travel with Jewish Singles and make new friends as you experience the highlights of Southern Italy and Sicily together!
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Our Tour Package includes:
- 11 Night Package in 4-star and 5-star Hotels
- 18 Meals – 11 Breakfasts, 7 Dinners
- English Speaking Tour Manager and Local Tour Guides
- Transportation and Daily Sightseeing as Outlined in the Itinerary
- Amazing Journeys Onsite Travel Coordinator
- All Taxes and Service Charges
- Gratuities for Tour Manager, Local Guides, Drivers, Porters, Servers at Included Meals
- Amazing Journeys Cocktail Party
- Baggage Handling Throughout (one bag per person)
- Amazing Journeys Gift for each Participant
- Amazing Service Throughout
Experiential Highlights include:
- Enjoy a welcome dinner featuring authentic Sicilian cuisine
- Walking tour of Palermo’s Byzantine, Arab, Norman and Spanish architecture
- Tour Teatro Massimo Opera House in Palermo
- Embrace Jewish History on a walking tour of Palermo’s Jewish past
- Experience the stunning Valley of the Temples (UNESCO) in Agrigento
- Discover Mt. Etna Volcano National Park (UNESCO)
- Spend the day in breathtaking Taormina in Sicily
- Traverse the region of Calabria in the “Boot of Italy”
- Wander through a local winery
- Experience wine tasting and regional cuisine as we enjoy dinner at a local winery
- Explore the Sassi de Matera (UNESCO) and ancient settlement of carved cave dwellings in Matera
- Discover an underground cistern OR whimsical Trulli homes
- Wind your way through the Amalfi Coast (UNESCO)
- Taste Limoncello at a local family’s factory
- Visit the Ruins of Pompeii (UNESCO)
- Take in the Vatican from a Jewish perspective
- And more!
What’s Not Included?
- Optional Tours and Entrance Fees not listed on the Itinerary
- International Flights
- Travel Protection
- Costs Related to Covid-19 Testing and Medical Expenses
- Arrival and Departure Transfers
- Meals not Mentioned on the Itinerary
- Beverages
- Arrival or Departure Airport Taxes
- Incidentals
Day 1 – Friday, May 19 – Palermo, Sicily – Tour Begins
Your Italian sojourn opens in Palermo, the capital of Sicily. Discover the city’s vibrant culture as you take in its picturesque harbors, cobblestone piazzas, and captivating energy. Tonight, join your fellow travelers for an Amazing Journeys Welcome & Orientation and Shabbat, followed by a welcome dinner featuring authentic Sicilian cuisine. (D)
Day 2 – Saturday, May 20 – Palermo
Get to know “Palermo in a Nutshell” and discover the city’s Byzantine, Arab, Norman, and Spanish architecture on a walking tour. Explore the Kalsa district – home to the anti-Mafia hero, Judge Giovanni Falcone, killed by the Mafia and its lush gardens such as Piazza Marina, the location where Joe Petrosino was killed by the Blackhand (Mafia). After, we will enjoy tasting local snacks at a 19th-century eatery. Tour the Teatro Massimo Opera House, the third largest in Europe and seen in The Godfather Part III. (B)
Day 3 – Sunday, May 21 – Palermo – Agrigento – Valley of the Temples
This morning we will explore the amazing Jewish history of Palermo. Strolling through the streets of the former Jewish Quarter you’ll learn about what was once the most beautiful Synagogue in all of Europe and what is the current status of Jewish culture in Palermo. Travel over rolling hills and peaceful farmland to the town of Agrigento. As the sun begins to set, explore the stunning Valley of the Temples (UNESCO), one of the world’s most esteemed archeological sites, and get an up-close view of the temples of Juno, Concordia, and Hercules. (B, D)
Day 4 – Monday, May 22 – Agrigento – Mt. Etna – Giardini Naxos
Journey east to Sicily’s Ionian Coast. En route, discover the impressive Mt. Etna (UNESCO) Volcano National Park where a local expert introduces you to the park’s spectacular landscapes sculpted by nature. Later this afternoon, continue on to Giardini Naxos – the “garden of Sicily” – for our 2-night stay. (B, D)
Day 5 – Tuesday, May 23 – Giardini Naxos – Taormina – Giardini Naxos
Set out for beautiful Taormina, home to ancient relics, rocky hills and charming gardens. With an expert local guide, you’ll see Corso Umberto, the verdant public gardens, and the city’s well-preserved Greek Theatre. Enjoy free time to relax or independently explore on your own. Return to Giardini Naxos for the evening. (B)
Day 6 – Wednesday, May 24 – Giardini Naxos – Matera
Take a short ferry ride to Villa San Giovanni, located on Italy’s mainland. Pass through the unspoiled region of Calabria to the Basilicata region. Wander through the twisting vines of a local winery before joining an expert for a tour of the cellar with a tasting. Linger over regional cuisine at dinner in the winery’s restaurant. (B, D)
Day 7 – Thursday, May 25 – Matera – Alberobello – Matera
Explore the Sassi di Matera (UNESCO), an ancient settlement of carved cave dwellings. A local guide shares the history and explains why film producers are seeking out this unique landscape. Visit a local shop and get a taste of regional specialties. This afternoon decide how you explore because it’s your choice! Discover more of Matera with a guided tour of an underground cistern followed by free time to browse the city’s stores and cave churches -OR- head to Alberobello (UNESCO) and marvel at the town’s whimsical trulli homes, known for their distinct, cone-shaped roofs. (B, D)
Day 8 – Friday, May 26 – Matera – Sorrento
After a stop in Vietri sul Mare, famous for its precious majolica pottery, arrive in Sorrento, where you’ll settle in for a 2-night stay. Later this afternoon, discover this charming seaside town during a walking tour and learn about the local tradition of wood marquetry. Join together this evening with our Amazing Journeys friends for our community Shabbat, followed by dinner. (B, D)
Day 9 – Saturday, May 27 – Sorrento – Amalfi Coast Drive – Sorrento
This morning, take in the sights and colors of the Mediterranean Sea as you wind your way along the breathtaking Amalfi Coast (UNESCO). Gaze out over the deep blue hues of the sea paired with the bright citrus fruits lining the hillsides. Pause to sample regional specialties at a family-owned limoncello factory, before returning to Sorrento for an afternoon at leisure. (B)
Day 10 – Sunday, May 28 – Sorrento Peninsula – Pompeii – Rome
Journey north to Rome. En route, experience the excavated ruins of Pompeii, a UNESCO World Heritage Site. A local guide gives you an in-depth look into this 2,000-year-old Roman town, nestled in the foothills of Mount Vesuvius. Step into another time as you explore its preserved buildings and imagine life in the 1st century. This afternoon, continue on to Rome, the capital of Italy and the seat of the Roman Empire. This evening you’ll have free time to roam Rome, enjoy some of the many piazzas and dine in a local trattoria. (B)
Day 11 – Monday, May 29– Rome
This morning we will delve into the history of Jewish Vatican. We’ll visit the Vatican, Vatican Museum and the Sistine Chapel as we explore the Jewish influence on the Catholic Church. Free time will be yours this afternoon to enjoy Rome on your own whether wandering the ancient streets, throwing three coins in the Trevi Fountain to ensure your next visit to the Eternal City or enjoying the best gelato ever! Tonight, join your fellow passengers for our Amazing Journeys Farewell, followed by dinner at a local restaurant. (B, D)
Day 12 – Tuesday, May 30 – Rome – Tour Ends
This morning we head back home with memories of our Amazing Journey. (B)
Our Hotels:
Day 1-2 NH Hotel, Palermo
Day 3 Baia di Ulisse, Agrigento
Day 4-5 Una Hotel Naxos Beach Sicilia, Giardini Naxos
Day 6-7 MH Matera, Matera
Day 8-9 Hotel Michelangelo, Sorrento
Day 10-11 Grand Hotel Flora, Rome
Please note:
– Alternate hotels may be used.
– The order of the tour may be changed.
– Some activities are weather dependent.
– Activity Level 3 out of 5 – This means you’re an on-the-go traveler. You don’t want to miss a thing, so walking and standing for 1-2 hours isn’t a big deal. You can navigate hills and uneven ground, climb into various modes of transportation and could possibly anticipate changes in elevation. You can expect some longer days balanced with free time to recharge or set out on your own.
Rates | Double | Single |
Sold Out | Sold Out |
A deposit of $650 is due with your reservation. Final payment is due on March 1, 2023.
Roommate matching is available.
Prices are subject to change based on availability.
Pre- and Post- Nights: We have a limited number of rooms for pre-tour overnights in Palermo. Rome rooms are not reserved but may be requested. Rates are listed per night and include breakfast and taxes. We are unable to provide roommate matching for pre- or post-night stays.
Palermo (May 17, 18)
Twin – $122 per person
Single – $244
Rome (May 30, 31 – based on availability – rates subject to change)
Twin – $249 per person
Single – $459
Please note – This is a group exclusive vacation package. We are unable to make any of our package components available to anyone who is not part of our Amazing Journeys group.
Items listed on this website are subject to change at any time. By providing payment you agree to the terms and conditions as outlined on this website. All rooms are non-smoking.
Cancellation Policy: From the time of deposit until November 14, 2022, there is a $100 penalty for cancellation. From November 15, 2022 – February 28, 2023, the cancellation penalty is $650. From March 1 – April 4, 2023 the cancellation penalty is 50% of the cost of the tour including additional nights pre- or post-tour. From April 5 – 17, 2023 the cancellation penalty is 75% of the cost of the tour including additional nights pre- or post-tour. From April 18, 2023 until the day of travel, the cancellation penalty is 100% of the cost of the tour including additional nights pre- or post-tour. Cancellations made on the day of departure and “no-shows” will receive no refund. There is no refund in the event of interruption or cancellation by the passenger after the start of the journey.
Travel Protection: Amazing Journeys recommends you purchase travel protection. Information will be sent with your tour confirmation.
Flights and Transfers: This tour begins in Palermo (PMO) and ends in Rome (FCO). Transfers between the airports and hotels are not included. Please don’t purchase your airline ticket until you have received a confirmation letter from Amazing Journeys.
Flight guidelines:
Tour begins May 19 – fly into Palermo, Italy (airport code PMO) no later than 3pm today. We will have an Amazing Journeys Orientation and Welcome – our first group event – this evening. You will leave the US on May 18th to arrive on May 19th.
Tour ends May 30 – fly from Rome, Italy (airport codes FCO or CIA) anytime today. FCO is the main international airport, but you may also find good flights from CIA.
Covid-19 Precautions: Until further notice, we require you to be fully vaccinated against Covid-19 at least two weeks before departure, and boosters are recommended to keep you healthy and safe while traveling but at this time, not required. We will be advising at a time closer to the time of travel if any documentation is necessary in order to enter Italy. Requirements are changing often and it is too early to gauge what the requirements will be at the time of travel.
Passports & Visas: A passport is necessary to travel on this itinerary. It must be valid for six months beyond the last day of the trip. If you are arriving from the US, Canada, Australia, UK, no visas are necessary at this time. Please note that visa requirements can change at any time and it is up to the traveler to be aware of visa requirements.
Fuel Surcharges: Should fuel charges be instituted for travel on this itinerary, the fees will be passed along to our travelers.
Exchange Rate: In the case of currency fluctuations of greater than 3%, we reserve the right to adjust our pricing accordingly in order that we may be able to operate the tour effectively.
Taxes & Gratuities: Taxes, surcharges, and government fees are subject to change. Gratuities have been included on this tour and include tips for the tour manager, local guides, drivers, luggage porters and included meals. Gratuities are not included for housekeeping staff in the hotels and tipping is at your discretion.
Activity Level: Activity Level 3 out of 5 – This means you’re an on-the-go traveler. You don’t want to miss a thing, so walking and standing for 1-2 hours isn’t a big deal. You can navigate hills and uneven ground, climb into various modes of transportation and could possibly anticipate changes in elevation. You can expect some longer days balanced with free time to recharge or set out on your own.
We must have a minimum of 19 participants in order to operate this tour.



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