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ROAD TO ROME

THE LIBERATION OF SICILY & ITALY IN WWII, 1943-44

Sept. 19-27, 2026

Ortigia coastline in Siracusa, Sicily, with historic buildings along the sparkling Mediterranean Sea. Visited on our Road to Rome tour, a site of ancient Greek battles and the 1943 Allied landings during Operation Husky in WWII.

Overview

ROAD TO ROME: THE LIBERATION OF SICILY & ITALY IN WWII, 1943-44

September 19-27, 2026

 

This fully guided and immersive trip will explore the people and places of the Italian Campaign from July 1943-June 1944, that began Europe’s liberation from Nazi rule. We will walk the beaches and cliffs and follow the operations from the Sicilian landing zones to the desperate fighting along the Gustav Line and Monte Cassino and on to the Anzio-Nettuno landings and the liberation of the Italian capital, the famed Eternal City.

 

The events of 1943-44 continue to inspire long after the guns have fallen silent. This Italy staff-ride will bring guests to the beaches, cliffs and fields; and villages, towns and cities where the Greatest Generation made their most indelible mark. From Rangers at Licata and Gela, to the American infantrymen assaulting the beaches at Paestum; from American paratroopers holding the key Biazza Ridge, and in the dizzying heights and intense fighting at Altavilla to the brutal slugfest fighting along the Rapido at San Pietro, and Cassino to the 3rd Infantry Division and the Ranger Force at Anzio-Nettuno and the final Ranger battle at Cisterna. Then, we will arrive in Rome to discuss the liberation of that city on June 4th and 5th, 1944, as well as visit so many other iconic sites!

 

The WWII expedition unfolds over nine days and eight nights with stories of all the Allied participants as well as those of the German defenders. In addition, we will see numerous examples of ancient Greek and Roman civilization – the heart of the Western World’s legacy.

your expedition leaders

$7,750 per person

StartSeptember 19, 2026
EndSeptember 27, 2026
Expedition Complete

$7,750 per person

Expedition Complete

Itinerary

  • Catania Arrival and Expedition Overview
    • Arrive at Catania, the capital of Sicily. Early arrivals may wish to explore the very fine Operation HUSKY museum in the town.
    • Check-in to Romano Palace Luxury Hotel near Catania International Airport.
    • We will have a welcome social and dinner and provide an overview of the expedition along with group introductions.
    • Hotel: Romano Palace Luxury Hotel.
  • End of the Expedition and Departures

    • Breakfast, followed by departures and onward journeys.

Inclusions

  • Nine days and eight nights of in-depth guided tours.
  • Full-time professional historian.
  • Breakfast at all hotels.
  • All museum and other entrance fees per itinerary.
  • Daily transportation on luxury bus.
  • Personalized tour support.
  • All breakfasts and lunches and dinners as identified on the itinerary.
  • Commercial flight from Catania to Naples.

Exclusions

  • Flights to/from Europe.
  • Airport transfers.
  • Alcohol, unless specifically included in the itinerary.



Please note that the tour begins in Catania, Sicily and ends in Rome.

Pricing

Our rates are based on double occupancy:

  • Double Occupancy: $7,750 per person ($15,500 total).
  • Single Occupancy: $8,550 per person (includes $800 supplemental fee).



Deposit and Final Payment

  • There is a $1,000 per person deposit required to confirm booking.
  • Final payment is due 90 days prior to start of expedition.
  • Pricing subject to change at final payment based on actual flight costs.
  • See Terms & Conditions here.
Product photo

Dr. Brian DeToy

EHE President & Co-Founder

Product photo

Jonathan Fursman

Expedition Director

Dr. Brian DeToy

Expert historian and expedition guide, Brian is a retired U.S. Army Infantry Officer who graduated from the University of Notre Dame with a BA in History and holds a PhD from Florida State University in European History.



While on active duty, he served as Director of the Defense & Strategic Studies program at the United States Military Academy, West Point, Assistant Professor in the Academy’s History Department, Chief of Research and Publications in the Combat Studies Institute at Fort Leavenworth, Kansas, and Professor of Military Science at the University of Kansas. He also served as the theater Command Historian for the Multi-National Corps-Iraq out of Baghdad.



Brian draws on his deep knowledge of military history and experience in the field to give EHE guests the most in-depth, personal look at not only the lessons of historical battles around the world but the cultures of the people who fought them.

Product photo

Dr. Brian DeToy

EHE President & Co-Founder

Product photo

Jonathan Fursman

Expedition Director

Jonathan Fursman

Jonathan is a retired U.S. Army Infantry officer who commissioned out of Cornell Army ROTC with a BA in Government. Jon also holds a Master of Public Policy from The George Washington University.



On active duty, Jon deployed as a combat leader to Iraq and Afghanistan multiple times, including as a rifle company commander in Baghdad in 2007. He was also an Assistant Professor of Defense & Strategic Studies at the United States Military Academy, West Point, NY for three years where he became an expert at leading staff rides. He later worked in Strategic Plans & Policy at U.S. Africa Command, commanded a Stryker infantry battalion, and served in the Republic of Korea for four years.



Today, he blends his professional military and teaching experience with his education in military strategy and public policy to deliver unique, thoughtful expeditions for EHE guests around the world.

Catania skyline with the majestic, snow-covered Mount Etna in the background, Sicily. First stop on our Road to Rome WWII expedition.

The HUSKY Landings and Initial Fights

  • Breakfast, load luggage and check-out of hotel.
  • Depart lodgings and drive southwest from Catania into the American landing zone.
  • Visit the landing beaches of George Patton’s US 7th Army, with the Ranger Battalions and the 3rd Infantry Division at Licata and Gela. The Sicily invasion was the war’s largest in numbers of men landed on D-Day.
  • Walk the Gela streets and waterfront where Colonel Darby and his Rangers hunted German tanks.
  • Lunch on your own in Gela.
  • In the afternoon visit the 1st Infantry Division’s inland battlesite at Casteluccio di Gela.
  • We will visit sites of the American advance inland, including Jim Gavin and the 505th PIR holding the key Ponte Dirillo Bridge and Biazza Ridge. Some of the stiffest fighting for the 82nd Airborne in the entire war! The 45th Infantry Division also saw hard action nearby at Piano Lupo.
  • Drive through the mountains to Siracusa in the British and Canadian zone. Siracusa is famed for its millennia of history. A crossroads of empires.
  • Walking tour of the Old Town on the island of Ortigia.
  • Group Dinner in Old Town.
  • Hotel: Five-star Ortea Palace by Autograph Collection.
American troops and landing craft on the beaches of Gela, Sicily, during the Allied invasion in Operation Husky, July 1943. Iconic image from the opening days of the Sicily campaign featured on our Road to Rome tour.
Sunlit Piazza Duomo in Siracusa with the grand Baroque Cathedral of Syracuse on the left. One of Sicily’s most beautiful squares, visited on our Road to Rome: The Liberation of Sicily & Italy in WWII tour.

The British Landings and Ancient Siracusa

  • Breakfast.
  • Visit British Commando and glider battle sites at Ponte Grande Bridge and on the Maddalena Peninsula as the British and Canadians attempt to gain a foothold.
  • Visit the Commonwealth War Graves Commission Cemetery at Siracusa.
  • In the afternoon, after lunch on your own, we will visit the ancient Greek sites and discuss the battles between Athens and Sparta and others here. “The Archaeological Park of Neapolis, in addition to the Greek Theatre of Syracuse, includes the Altar of Hieron II, a commemorative monument dedicated to Zeus Eleutherios, the Roman Amphitheatre from the 34th Century AD, the most important public work of the time, the Ear of Dionisio from which the route of the large urban quarries starts.”
  • Then, it’s off to the val de Noto to visit a winery where olive oil is also produced. Sicilian cuisine requires these two critical ingredients, and we will discover the millennia-old process. Val di Noto, a UNESCO World Heritage site in southeastern Sicily, is a prestigious wine region known for its native grape varieties, particularly Nero d'Avola (red) and Moscato di Noto (white). The region's ideal conditions—limestone soils, a Mediterranean climate, and a history of post-earthquake rebuilding in the Baroque style—create a unique wine tourism experience. You can explore many wineries there, such as Feudo Maccari, Cantina Fausta Mansio, and Tenuta Bastonaca, offering tastings of wines made from these iconic local grapes.
  • Social hour followed by dinner on your own in the Old Town with its myriad restaurants.
  • Hotel: Ortea Palace.
Close-up of ancient Greek stone carvings at the Theater of Neapolis in Siracusa, highlighting Sicily’s rich classical heritage.
Nero d’Avola grapes on the vine in the Val di Noto wine region of Sicily. Featured during our winery stop exploring one of Sicily’s most important native grape varieties.

Primosole, Magical Taormina, & Flight to Naples

  • Breakfast and checkout with luggage.
  • Drive to central Taormina. We drive north along the British 8th Army route to the strategic Catania Plain, the focus of the British advance. We will discuss the incredible dayslong battlesite at Primosole Bridge, perhaps the toughest British action in the war.
  • Afternoon visit to Taormina, the gorgeous cliffside town, renowned for its actors and performers from ancient Greek theater to Hollywood fame. Lunch on your own in town.
  • Drive to Catania airport for late afternoon flight to Naples.
  • Arrive Naples, meet bus and drive south to the AVALANCHE landing beaches and the town of Pompeii.
  • Check-in to lodgings.
  • Dinner at the hotel.
  • Hotel: MGallery Habita 79.
General Montgomery and Lieutenant General Patton studying a map of Sicily during the Allied campaign in 1943.
Ancient Greek Theatre of Taormina, Sicily, with its dramatic ruins overlooking the sparkling Ionian Sea and the town below. A highlight stop on our Road to Rome tour combining ancient history with the beauty of Sicily.

Operation AVALANCHE, Magna Graecia, & Amalfi

  • Breakfast.
  • Explore the September 9, 1943, landing beaches of Mark Clark’s US 5th Army, especially the 36th Division at Paestum in Operation AVALANCHE.
  • A visit to the ancient Greek ruins of Paestum is followed by lunch at the museum. This Magna Graecia site is one of the oldest, largest and best-preserved in the ancient world. Older than the Parthenon atop Athens’ Acropolis!
  • In the afternoon, visit other small-unit battles sites include the Tobacco Factory complex, and the tough fight in the clouds at Altavilla with elements of the 82nd Airborne and 36th IDs.
  • Drive to Amalfi, perched above the azure Mediterranean on the gorgeous Amalfi Coast. You will have time to explore the amazing town of Amalfi on your own.
  • Drive to Chiunzi Pass, site of an incredible Ranger defense at the rugged Chiunzi Pass in September 1943.
  • Social hour followed by dinner on your own in one of the many wonderful restaurants in Pompeii.
  • Hotel: MGallery Habita 79.
American soldiers of the 143rd Infantry Regiment coming ashore at Salerno, Italy, as part of Operation Avalanche in 1943.
Ancient Greek temples at Paestum, one of the best-preserved Magna Graecia archaeological sites in Italy. These exceptionally well-preserved Doric temples date back over 2,500 years.

The Battles at the GUSTAV Line and Cassino

  • Breakfast.
  • At San Pietro Infine, we will observe the brutal fight against a formidable enemy and equally formidable terrain. The 36th Division sustained many losses but took the town (though totally destroyed and this day a national park). Famed war correspondent Ernie Pyle wrote his most eloquent dispatch about this fight – “The Death of Captain Waskow.” John Huston made an acclaimed war documentary during the battle.
  • Our next stop is the Rapido River crossings at Sant Angelo in Theodice. The battle here, to break the stalemate at Cassino, resulted in one of the bloodiest setbacks of the war in Italy. We will have a box lunch along the riverside.
  • In the rebuilt city of Cassino, we will discuss the four attacks by Americans, New Zealanders, Indians and finally Poles to capture the high-ground behind.
  • We will visit the amazing Abbey of Monte Cassino, one of the most important sites in all Christendom and one that dominates the road to Rome. Its destruction by allied bombing remains one of the most controversial decisions of the entire war.
  • We will visit the nearby Polish Cemetery where we can observe the final fight up the forbidding terrain resulting in its capture.
  • Drive to Nettuno.
  • Check-in to lodgings on the Anzio-Nettuno landings beach.
  • Social hour followed by dinner on your own.
  • Hotel: Astura Palace.
Ruins of a stone building in the devastated town of San Pietro Infine along the Reinhard Line, captured at heavy cost by the 36th Infantry Division in 1943 and famously documented by war correspondent Ernie Pyle.
Panoramic view of the Liri Valley from inside the historic Abbey of Monte Cassino, a key strategic site in the Allied advance toward Rome in 1944.

Operation SHINGLE at Anzio and Nettuno

  • Breakfast, load luggage and check out of the hotel.
  • In the pre-dawn darkness of January 22, the Ranger Force landed at Anzio and quickly seized the vital port, spearheading the invasion in Operation SHINGLE, an attempt to turn the Germans out of their Gustav Line positions. The main American force landed at nearby Nettuno and we will visit the beach.
  • Our next stop is one of the most pivotal actions for the Rangers in WWII. At Cisterna, on January 30th, Darby’s Ranger force faced overwhelming odds and was itself destroyed in a fierce battle that few survived. The remains of the 1st, 3rd and 4th Battalions were dismantled and the survivors sent back stateside to train new Rangers.
  • Group lunch in Cisterna.
  • Visit the nearby Sicily-Rome American Cemetery where over 7,000 Americans lie in a spectacularly beautiful resting place maintained by the American Battlefields Monuments Commission.
  • Check-into our beautiful lodgings in Rome, located directly on the Piazza Navona.
  • Social hour with Reflections followed by dinner on your own in Rome.
  • Hotel: Five-star Eitch Borromini.
Soldier from the 3rd Infantry Division standing amid the ruins of Cisterna, Italy, in May 1944 after the town was finally secured. Cisterna was the scene of the costly Ranger assault earlier in the Anzio campaign.

The Liberation of Rome

  • Breakfast.
  • Walk through central Rome to Via Rasella, site of April 1944 Resistance attack. Discuss the operation and subsequent events.
  • Our next stop will be the moving Ardeatine Cave Massacre site and memorial. Italian civilians were brutally murdered here in April 1944 by German SS in retaliation for a partisan ambush in Rome.
  • At St Paul’s Gate, we will visit sites of Rome’s June 1944 liberation by the US-Canadian 1st Special Service Force, as well as battles against the Germans by Italians in September 1943. The nearby English or Protestant cemetery includes the graves of Keats, Shelley and others.
  • In the afternoon, you will have time to explore Rome with lunch on your own.
  • Later in the afternoon, we will visit the vibrant Jewish Quarter with a final group dinner and farewells.
  • Hotel: Eitch Borromini.
The moving Brothers in Arms memorial at the Sicily-Rome American Cemetery, commemorating fallen U.S. soldiers of the Italian Campaign.
The iconic Colosseum in Rome, one of the greatest architectural wonders of the ancient world and a highlight visit on our Road to Rome tour.