Italy in WWII: Sicily to Rome
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Date(s) - 08/08/2019 - 17/08/2019
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Italy in WWII: Sicily to Rome

AUGUST 8-17, 2019

Take an unforgettable 10 day journey along beautiful coasts to visit incredible Italian battlefields of the Second World War. In addition to its renown as one of the cradles of Western civilization, Italy also holds profound monuments to World War II such as the ghost town of San Pietro and the battle sites of Gela, Monte Cassino and Anzio. On this once-in-a-lifetime journey, we will experience the legacy of the Roman Empire and follow the footprints of Allied and German soldiers as they waged battle for the future of Europe and the world. Beyond the indelible stories of war, we will be sure to taste the delicious cuisine, admire Italy’s incredible natural beauty and the finest examples of architecture in the country that is home to the world’s greatest number of UNESCO World Heritage Sites.

Trip highlights will include:

  • Operation HUSKY – Sicily landing beaches in the largest invasion day in world history
  • Allied WWII Landings Museum in Catania, the “capital” of Sicily at the base of Mount Etna
  • Operation AVALANCHE – Salerno (Paestum) landing beaches on the Italian mainland south of Naples
  • The Abbey of Monte Cassino – scene of the toughest fighting in the hard slog up the Italian “boot”
  • San Pietro Infine: an ethereal ghost town preserved from WWII
  • Operation SHINGLE – Anzio and Nettuno landing beaches at the southern gateway to Rome
  • Sicily-Rome American Cemetery – an amazingly beautiful homage to America’s fallen
  • Rome – from Caesar and the Republic through the Empire to Mussolini and on through today
  • Spectacular meals, drinks and natural beauty
Essential History Expeditions


While Europe is, of course, accessible to American travelers on their own, fully understanding a major WWII campaign, so large in scale and scope, requires months if not years of preparation. A professional, guided experience is essential in comprehending the complexities of the events and their timing, specific locations and personalities. Tours are available through many companies in Italy. What sets Essential History Expeditions and Dr. Brian DeToy apart is his unique experience with 14 years as a university professor including teaching history and strategic studies at West Point, 28 years as a US Army officer with combat experience, and 23 years of leading tours of battlefields and cities. Brian’s many tours, both large and small, include military leaders, West Point professors and cadets, and business leaders of international companies, history buffs and families. Brian’s combined experience as a scholar soldier brings the events to life.

If a guest has a family member who served in Italy in WWII, Brian will research the service member’s unit and weave that information into the tour, visiting all relevant locations and markers. Previous guests find this personalized approach to be emotionally gratifying and memorable.

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WWII Sicily Essential History Expeditions

Day 1, August 8th: Introduction to Italy in WWII

We greet our guests at Catania International Airport in Sicily and transfer them to our lodgings. Free time is available to settle in, spend time in the hotel or enjoy a walk around town. The expedition’s events begin in the evening with a welcome social hour, dinner and overview of the tour program.

Day 2, August 9th: Operation HUSKY and Gulf of Noto

We tour the landing sites of Operation HUSKY from Gela to Licata, followed by a visit to the memorial dedicated to the 82nd Airborne close to the Ponte Dirillo Bridge. In the afternoon we explore the British and Canadian landing sites on the Gulf of Noto.

Day 3, August 10th: Catania & Motta St. Anastasia

In the morning we visit the Historical Museum of the Landings in Catania, one of the best WWII museums in the world. Afterwards we take a walking tour in the Baroque city center. In the afternoon we visit the Commonwealth War Cemetery located in a grove just outside of Catania with a view of Mount Etna, the highest active volcano in Europe. From here we go to the valley of Motta St. Anastasia to visit the German War Mausoleum. Dinner on your own in Catania this evening.

Day 4, August 11th: Paestum & Operation AVALANCHE

We take a short flight across the azure waters of the Tyrrhenian Sea from Catania to Naples and then take the bus for the quick trip down the coast to Paestum. We tour the beaches of Operation AVALANCHE in the Paestum area related to the Salerno landings. We will also visit the spectacular Greek and Roman ruins here.

WWII Italy guided tours
Italy guided history tour

Day 5, August 12th: Pompeii & Cassino

In the morning we drive to Pompeii and explore the famously preserved ancient site under the watchful eye of Mount Vesuvius. We then travel on to Cassino. Hotel night in Cassino or nearby.

Day 6, August 13th: Monte Cassino & San Pietro Infine

We head to the reconstructed Benedictine Abbey of Monte Cassino, where we will discuss the offensive against the Gustav Line and tour numerous sites of this amazingly bitter battle. We then drive to San Pietro Infine, a village frozen in time as it was abandoned during the heavy fighting. It now serves as a monument to the suffering and devastation caused by war. Hotel night in Cassino or nearby.

Day 7, August 14th: Landing Beaches & Operation SHINGLE

We start the day visiting the landing beaches and battle sites near Anzio and Nettuno, the site of the amphibious landing of Operation SHINGLE in January 1944. We will also pay our respects at the Sicily-Rome American Cemetery and Memorial, where 7,862 American soldiers are interred in a spectacularly beautiful setting. We then head to Rome for the night.

Day 8, August 15th: Incomparable Rome

We tour the Eternal City with visits to sites of its thousands of years of history, including those related to World War II.

Since no visit to Rome can be complete without seeing the Colosseum and the Forum, we discover the most important ancient remains of the Italian capital on a guided tour. In the afternoon we offer free time and a chance to other famous sites like the Trevi Fountain, the Pantheon and the Spanish Steps. Dinner on your own this evening.

Day 9, August 16th: Ancient to Modern Rome

In the morning, we will visit St Peter’s Basilica, including Michelangelo’s sublime La Pietà, tour the Vatican, including Michelangelo’s incomparable Sistine Chapel. Nearby, we’ll visit the Museo Nazionale di Castel Sant’Angelo. Next, we’ll visit San Pietro in Vincoli, home of Michelangelo’s statue of Moses as well as the chains used to bound Saint Peter when he was imprisoned in Jerusalem. You will have the afternoon to explore on your own before our final group dinner.

Day 10, August 17th: Onward Journeys

In the morning, we transfer our guests to Rome’s Leonardo da Vinci International Airport for their return flights home or onward to London to join the next phase of this amazing World War Two expedition – “England, Normandy and the Liberation of Paris at 75”

WWII Italy history tour
Italy historical tours
guided history tours WWII Italy


  • Nine and a half days of in-depth guided tours, led by an expert historian
  • Accommodations for eight nights
  • All transportation after joining the group in Sicily through Rome, including internal flight
  • All meals included except as specified in the itinerary
  • All museum and activity entrance fees
  • Personalized tour support
  • Alcoholic drinks are EXCLUDED
Italy history tour


  • Let’s set up a conference call! We would love to chat with you to answer any questions you may have!
  • Just complete the contact form below and let’s set up a call.


  • Pricing: $4,350 per person, double occupancy; $700 single occupancy supplement.
  • Down payment: $1,000 per guest due upon registration.
  • All active duty and career retired military, current and career retired educators, and students will receive a 10 percent discount on the Normandy tour.
  • All repeat guests of Essential History Expeditions receive a 10 percent discount on all future expeditions.
  • Itinerary subject to slight change.
  • Please see Terms and Conditions for payment schedule and cancellation policy.
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