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What’s new?
be inspired
why gil travel
Middle East
Western Europe
Eastern Europe
Latin America
Asia/ South Pacific/ Africa
North America
Oceana
From $6,120
OVERVIEW
Embark on an extraordinary journey through Puglia and Basilicata, two of Italy’s most captivating regions, where the hidden Jewish heritage of southern Italy awaits to be uncovered. With breathtaking sea views, charming medieval towns, and a rich culinary landscape, this tour offers a unique opportunity to connect with a lesser-known chapter of Jewish history. Explore stunning landscapes, indulge in delicious regional cuisine, and immerse yourself in centuries of Jewish resilience while savoring the vibrant flavors of Italy.
Departures
Duration
Highlights
Notes
Activity Level
Tailor Made
Itinerary
Price Per Person: $6,120 based on sharing a room. Single Supplement: $1,970
Kosher Standards: Glatt Kosher, Chalak Beit Yosef, Shomer Tmidi.
Price Includes:
Transportation: Air-conditioned tourist luxury bus with 48 seats
Guide: 7 days of leading and guiding by Moshe Ben Simon, with additional local guides when necessary
Price Does Not Include:
Flight:
ITA Airways AZ609/AZ1621
Departure:
June 4th from JFK at 20:55
Arrival:
June 5th at Brindisi Airport at 10:30
Upon arriving at Brindisi Airport at 11:00 AM, the group will gather to begin this exciting journey. The transfer to your private accommodation at the luxurious Masseria Leili winds through scenic countryside.
Once at the Masseria, a delightful welcome lunch featuring local flavors awaits, introducing you to Puglia’s rich culinary traditions.
After settling in, the afternoon is yours to explore Lecce. Stroll through its charming streets and admire the city’s stunning Baroque architecture.
As evening falls, the group gathers back at the Masseria for a delicious dinner, setting the tone for a remarkable adventure ahead.
The day begins with a buffet breakfast before setting out for a guided tour of medieval Lecce. The city’s Jewish quarter, with its historic significance, offers fascinating insights into a rich cultural past. As you explore notable landmarks like the Belloluogo tower and the Roman Amphitheatre, the history of this ancient city comes to life.
In the afternoon, we will visit Palazzo Taurino and the Jewish Museum, where you will learn about the Jewish community’s history in Lecce while sampling Kosher Salento wine and local kosher delicacies.
Later, enjoy some free time to soak in the city’s vibrant atmosphere before heading back to the hotel to prepare for Shabbat.
Kabbalat Shabbat is celebrated at the Masseria, where tradition meets the beauty of southern Italy.
Shabbat unfolds in the peaceful surroundings of the Masseria. After Shacharit and followed by Kiddush, the Shabbat buffet lunch showcases the chef’s culinary talents, offering a feast of delicacies.
The afternoon is a time to rest and reflect—whether by the pool or amidst the serene beauty of the estate grounds.
As the day comes to a close, Havdalah brings the group together before heading out for a leisurely evening in Lecce, where the city’s charming streets and local culture offer the perfect way to unwind.
The morning begins with a visit to the Castellana Prehistoric Caves, a fascinating natural wonder. As you hike through the caves, the awe-inspiring stalactites and stalagmites transport you to a world millions of years in the making.
Next, the coastal town of Monopoli awaits. Here, a light lunch and a stroll through its historic streets allow you to uncover hidden gems and enjoy the vibrant atmosphere.
The day continues with a visit to Polignano del Mare, where dramatic cliffs overlook the Adriatic Sea, offering stunning views before returning to the comfort of the Masseria for a wonderful dinner.
After breakfast, the day’s journey begins with a visit to the iconic Trulli houses in the village of Alberobello. These unique cone-shaped structures are a hallmark of the region, and a guided tour offers insights into their history.
A stop at Casa Rossa provides a moving connection to the Jewish refugees who found shelter there during World War II.
The next destination is an olive oil farm near Ostuni. You will learn about the traditional production of olive oil, visit ancient olive trees, and indulge in a tasting session with lovely canapes prepared by our chef.
Lunch is served on the farm, with the rich flavors of the region highlighted. The day concludes with a walking tour of Ostuni, where the city’s white-washed houses, ancient defensive walls, and Gothic cathedral stand as testaments to its history.
Returning to the Masseria in the evening, you can relax before enjoying another exquisite dinner paired with Italy’s finest kosher wines.
The historic city of Matera beckons, with its ancient Sassi cave-dwelling districts offering a window into centuries of life carved into the cliffs. As you wander through Matera’s narrow lanes, you explore cave churches and discover the old Jewish quarter, delving into the area’s deep history.
The stories of Matera’s past unfold during the day, leaving you with a sense of wonder as you return to the hotel. The scenic drive back to the Masseria provides the perfect opportunity to reflect on the day’s extraordinary experiences.
The adventure continues with a visit to Nardò, where medieval walls still guard parts of the town, and the Jewish section tells stories of resilience. In nearby Santa Maria al Bagno, we will visit the Jewish Museum, where murals tell the moving stories of Jewish refugees who found shelter here between 1944 and 1947.
From there we head to Gallipoli, a town perched on an island with stunning Baroque architecture and captivating sea views.
The final destination of the day is Otranto, where the city’s bastions and the Aragonese castle transport you back to the Middle Ages. The visit includes a tour of the famous cathedral, with its intricate mosaic floor depicting stories from the Old Testament.
The day concludes with some free time to explore Otranto at your own pace before heading back to the Masseria.
After an early breakfast, it’s time to say goodbye to the beauty of Puglia as you prepare for your departure.
The scenic ride to Brindisi Airport allows you one last glimpse of the landscape that has been your home for this unforgettable journey.
For those wishing to extend their adventure, a weekend in Rome or Venice with a Jewish heritage tour is available upon request.
Full payment due upon registration.
59 – 30 days before departure: Refundable minus 50% of total cost.
Less than 30 days before departure (after May 16): 100% non-refundable.
In cases of force majeure/COVID-19 cancellations, a full refund will be
provided minus $330 per person.
Travel Insurance
We strongly recommend purchasing comprehensive travel insurance to cover any
cancellation fees, medical expenses, lost luggage, or other potential losses.
Accommodation
Masseria LiLei is a luxurious countryside retreat located in Lecce, Italy. It’s a beautifully restored 15th-century fortified farmhouse that blends historic architecture with modern amenities.
*Star rating standards vary from country to country.
Start your adventure here
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