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TRULLI OF PUGLIA AND MATERA OF BASILICATA
May 14-22, 2025

Starts in Brindisi and also visit Lecce, Oria, Cisternino, Ostuni, Matera, Martina Franca, Foggia, San Vito, Mesagne, Gillipolo and Taranto.

Nestled in the sun-kissed heel of Italy's boot, Puglia dazzles visitors with its picturesque landscapes, rich history, and culinary delights. Known as the "heel of the boot," Puglia boasts a diverse terrain that ranges from the azure Adriatic Sea to the rugged Apennine Mountains.  Its coastline stretches along the Adriatic and Ionian Seas, offering stunning beaches, limestone cliffs, and hidden coves.  Trulli, iconic cone-shaped houses, dot the countryside, adding a touch of whimsy to the rustic landscape.  The region's history is woven into its architecture, with ancient cities like Lecce, known as the "Florence of the South," showcasing Baroque masterpieces alongside Roman ruins and Norman castles.  Puglia's culinary scene is equally enticing, with fresh seafood, artisanal olive oil, and robust wines tantalizing the taste buds of visitors.

In the rugged terrain of the Basilicata region, Matera stands as a testament to human resilience and ingenuity.  Carved into the limestone cliffs of the Gravina River gorge, Matera's ancient Sassi districts are among the oldest continuously inhabited settlements in the world.  The city's labyrinthine streets wind through a mesmerizing maze of cave dwellings, churches, and palaces, earning Matera recognition as a UNESCO World Heritage Site.  Its haunting beauty has captured the imagination of filmmakers, with Matera serving as the backdrop for numerous cinematic productions, including Mel Gibson's "The Passion of the Christ."  Beyond its historical allure, Matera embraces a vibrant cultural scene, with festivals, art exhibitions, and culinary events celebrating the region's rich heritage.

You will be guided by an Italian insider, Phil of Philítaly.  He will leverage his Italian language, access to family and friends to show you the real Italian “day in the life”, and take you to places off the beaten path.

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9 DAYS / 8 NIGHTS
May 14-22, 2025

Price for Full Land Package All Inclusive $ TBD Per Person

 

Purchase your flight on your own to have more control over possible changes.  Choose a flight from the closest airport with non-stop flights to the Italian hub city where the group meets.  If you are not close to a city with non-stop service to the hub in Italy, we suggest you take a domestic flight to the US city that offers non-stop service to Italy hub or fly to a European city with layover to the hub city in Italy where the group meets. ​

Consider travel insurance for peace of mind to protect land, air and trip cancellation as well as medical service and evacuation insurance.  Click here to view options for comprehensive insurance, not just for flight cost, like most airlines sell. 

Day 0, Tuesday May 13, 2025

Travel overnights from US or early morning from a European City
Arrive in Brindisi.
Meet your private driver outside baggage claim.
Day 1, Wednesday May 14, 2025
Arrival and Exploration in Brindisi
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Morning

  • Free time for you to relax or explore in Brindisi 
     

Afternoon/Evening

  • Walking tour of Brindisi then dinner at the hotel

  • An evening stroll following dinner

  • Sleep in Brindisi

Day 2, Thursday May 15, 2025
Cultural Immersion in Brindisi and Lecce
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Morning

  • Visit the Cloister of San Benedetto and mother church as well as explore the Roman Columns
     

Afternoon/Evening

  • Travel by private motor coach and spend the afternoon in Lecce followed by dinner then travel back to Brindisi

  • Sleep in Brindisi

Day 3, Friday May 16, 2025
Discovering Oria, Alberobello, Cisternino, and Ostuni
Image by Raunaq Patel

Morning

  • Travel by private motor coach to Oria with stops along the way to visit an ancient castle and Albero Bello with the famous Trulli
     

Afternoon/Evening

  • Travel back to Brindisi with stops in Cisternino and Ostuni

  • Dinner in Cisternino

  • Sleep in Brindisi

Day 4, Saturday May 17, 2025
Journey to Matera and Basilicata Region
Image by Giuseppe Mondì

Morning

  • Travel by private motor coach to Matera in the Basilicata region with a stop along the way in Martina Franca where you will have lunch. 
     

Afternoon/Evening

  • Walking tour of the city of Matera

  • Sleep in Matera Albergo

Click here to learn more about Matera 

Day 5, Sunday May 18, 2025
Exploring Foggia, San Vito, and Mesagne
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Morning

  • Depart from Matera and travel by private motor coach back to Brindisi with a stop along the way in Foggia which is in the Puglia region
     

Afternoon/Evening

  • Lunch in Foggia with stops afterwards in San Vito and Mesagne. Light dinner in Brindisi

  • Sleep in Brindisi

Day 6, Monday May 19, 2025
Beach Relaxation and Cooking Class in Puglia
Beach

Morning

  • Spend the morning on the white sandy beach of Puglia
     

Afternoon/Evening

  • Spend a little more time on the beach followed by a local cooking class where you will learn how to make Orecchiette con salsiccia e cima di rapa 

  • Sleep in Brindisi

Day 7, Tuesday May 20, 2025
Day Trip to Gallipoli and Taranto
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Morning

  • Travel by private motor coach for a day trip to Gallipoli and Taranto where you will relax and take a walking tour after lunch which will be in Taranto
     

Afternoon/Evening

  • Back to Brindisi where you will enjoy a light dinner

  • Sleep in Brindisi

Day 8, Wednesday May 21, 2025
Cultural Highlights and Maritime Adventure in Brindisi
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Morning

  • Spend the morning at a farmhouse church and the Cloister of San Giovanni right in Brindisi
     

Afternoon/Evening

  • Explore the Maritime Monument and then take a boat ride along the coast

  • Sleep in Brindisi

Day 9, Thursday May 22, 2025
Farewell and Departure from Brindisi
Breakfast

Morning

  • Enjoy your last delicious breakfast before departing for your next destination whether it be home or another European city

Choose another Philìtaly Adventure to explore below

Image by Giulia Gasperini
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TRULLI OF PUGLIA AND MATERA OF BASILICATA
May 14-22, 2025

Starts in Brindisi and also

visit Lecce, Oria, Cisternino, Ostuni, Matera, Martina Franca, Foggia, San Vito, Mesagne, Gillipolo and Taranto.

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visit New York, Quebec City and Toronto.

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March 20-28, 2025

Starts in Rome and also

visit Vico Equense, Amalfi, Ravello, Paestum, Battipaglia, Pompei, Campobasso, Oratino and Agnone.

A group of curious travelers interested in places off the beaten path and not known to tourists, where the culture, food, wine and music are regionally preserved.

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EXPLORE CENTRAL SOUTH ITALY
May 1-9, 2025

Starts in Rome and also

visit Vico Equense, Amalfi, Ravello, Paestum, Battipaglia, Pompei, Campobasso, Oratino and Agnone.

A group of curious travelers interested in places off the beaten path and not known to tourists, where the culture, food, wine and music are regionally preserved.

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ITALY IN ARGENTINA
October 17-26, 2024
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also visit Tigre, San Isidro and Mendoza.

Open to the public for those who want to see how Italy influences the culture of Argentina, and vice versa.

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EXPLORE CENTRAL SOUTH ITALY
November 7-15, 2024

Starts in Rome and also

visit Vico Equense, Amalfi, Ravello, Paestum, Battipaglia, Pompei, Campobasso, Oratino and Agnone.

A group of curious travelers interested in places off the beaten path and not known to tourists, where the culture, food, wine and music are regionally preserved.

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THE SPLENDORS OF CENTRAL AND
NORTHERN ITALY
June 25-July 4, 2024
This is a suggested itinerary for one or more people traveling. It can be modified by the travelers and price modified accordingly.

Starts in Rome and also

visit Ravenna, Ferrara, Bologna, Florence, Assisi and Farfa.

Customized experience for a private group.

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Learn more about Playing for Pizza ▾

#1 NEW YORK TIMES BESTSELLER 


Playing for Pizza: A Novel by John Grisham Published in 2012

American National Football League third string quarterback for the Cleveland Browns, Rick Dockery becomes a national laughing-stock after what is considered the worst performance in NFL history. No other NFL team wants him after he is cut by the Browns.

 

Against all odds he lands a job as the starting quarterback for the Parma, Italy Mighty Panthers. The Parma Panthers are happy to have Rick, wanting an NFL player and not being selective about which former American NFL player they choose.

For Rick, not knowing anything about Parma and not speaking a word of Italian, a series of adventures ensue bringing with it a few surprises.

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EXPLORE CENTRAL SOUTH ITALY
September 13-21, 2024

Starts in Rome and also

visit Vico Equense, Amalfi, Ravello, Paestum, Battipaglia, Pompei, Campobasso, Oratino and Agnone.

A group of curious travelers interested in places off the beaten path and not known to tourists, where the culture, food, wine and music are regionally preserved.

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March 14-22, 2024

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visit Campobasso, Agnone, Naples, Amalfi Coast, Pompei, Vico Equense and Battipaglia.

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CLE SICILY (SOLD OUT)
March 22-27, 2024

Starts in Palermo and also

visit Alimena, Cefalù, Taormina and Agrigento.

A private Ohio-based group of friends exploring Sicily.

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April 4-April 12, 2024

Starts in Palermo and also

visit Monreale, Agrigento, Catania, Taormina, Siracusa, Ortigia, Trapani, Montalbano Elicona and Cefalù.

A group of 25 travelers (including you?) with Sicily on bucket list.

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CLUB AND CLASS REUNIONS
Dates selected by client

Starts in town of your choice

Customized experience for a private group.

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FAMILY HERITAGE REUNIONS
Dates selected by client

Starts in your ancestry town

Customized experience for a private group.

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O SOLO MIO - For solo or small group traveler(s)
Dates selected by client

Open to the public, an experience you define for yourself or a small group of travelers.

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ENERGY INDUSTRY EXECUTIVES
TBD 2026

Starts in Rome

Open to the public, a group of professionals working in the Energy sector.

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DESTINATION WEDDINGS IN ITALY
Dates selected by client