Italy in WWII: from Sicily to Rome | History Tours | Private & Group Educational Tours

Map Unavailable

Date/Time
Date(s) - 19/09/2026 - 27/09/2026
12:00 am

Categories No Categories

The Greatest Generation in Italy: From Sicily to Rome, 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 3^rd 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 4^th 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.

ACTIVITIES & HIGHLIGHTS

Day 1

SATURDAY, SEPTEMBER 19th: 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 or similar

Day 2

SUNDAY, SEPTEMBER 20th: 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 7^th Army, with the Ranger Battalions and the 3^rd 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 1^st Infantry Division’s inland battlesite at Casteluccio di Gela.
We will visit sites of the American advance inland, including Jim Gavin and the 505^th PIR holding the key Ponte Dirillo Bridge and Biazza Ridge. Some of the stiffest fighting for the 82^nd Airborne in the entire war! The 45^th 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: Ortea Palace by Autograph Collection or similar

Day 3

MONDAY, SEPTEMBER 21st: 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 34^th 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.
Social hour, followed by dinner on your own in the Old Town with its myriad restaurants.
Hotel: Ortea Palace or similar

Day 4

TUESDAY, SEPTEMBER 22nd: SIRACUSA to CATANIA WITH THE 8th ARMY

Breakfast and checkout with luggage.
Drive north along the British 8^th Army route to the strategic Catania Plain, the focus of the British advance.
Visit 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 Paestum.
Check-in to lodgings.
Dinner at the hotel.
Hotel: Mec Paestum

Day 5

WEDNESDAY, SEPTEMBER 23: AVALANCHE LANDINGS AND INITIAL FIGHTS

Breakfast
Explore the September 9, 1943, landing beaches of Mark Clark’s US 5^th Army, especially the 36^th 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.
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 82^nd Airborne and 36^th IDs.
Drive to famed Amalfi and check-in to Luna Convento
Social hour followed by dinner on your own in one of the many wonderful restaurants in Amalfi.
Hotel: Luna Convento or similar

Day 6

THURSDAY, SEPTEMBER 24th: THE RANGERS AT CHIUNZI PASS AND ON TO THE BATTLES AT CASSINO AND THE BREAKING OF THE GUSTAV LINE

Breakfast
In the morning, we examine the Ranger Force operations to secure the vital Chiunzi Pass to the north. A significant battle here enabled the allies to advance on Naples.
At San Pietro Infine, we will observe the brutal fight against a formidable enemy and equally formidable terrain. The 36^th 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.
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.
Hotel: Austura Palace or similar

Day 7

FRIDAY, SEPTEMBER 25th: OPERATION SHINGLE & BREAKING THE LINE

Breakfast
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 30^th, Darby’s Ranger force faced overwhelming odds and was itself destroyed in a fierce battle that few survived. The remains of the 1^st, 3^rd and 4^th Battalions were dismantled and the survivors sent back stateside to train new Rangers.
Group lunch in Cisterna.
In the afternoon, visit the battle of the Caves from February 1944, the most desperate action of the beachhead. The TV series, The Liberator, captures scenes here.
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.
Social hour, with Reflections, followed by dinner on your own in Nettuno.
Hotel: Austura Palace or similar

Day 8

SATURDAY, SEPTEMBER 26TH: THE CAPTURE & LIBERATION OF ROME

Breakfast and load luggage and check-out of hotel.
Continuing on to Rome, we will follow the May 1944 breakout from the beachhead by MG Lucian Truscott’s VI Corps.
In the morning, we will visit 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.
We will also 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.
In the afternoon, we will visit the vibrant Jewish Quarter and its synagogue and Shoah museum.
Group lunch in the Jewish Quarter.
Drive to central Rome lodgings.
Final group dinner to wrap-up the expedition.
Hotel: Pantheon Iconic Rome Hotel, Autograph Collection or similar

Day 9

SUNDAY, SEPTEMBER 27TH: END OF THE EXPEDITION AND DEPARTURES

Breakfast, followed by departures and onward journeys.

THIS EXPEDITION INCLUDES

Nine days and eight nights of in-depth guided tours.
Full-time professional historian.
All single occupancy lodging in best hotel available in each location: 1 night in Catania, 2 nights in Siracusa, 1 night in Mec Paestum, 1 night in Amalfi, 2 nights in Nettuno and 1 night in Rome.
Breakfast at all hotels
All museum and other entrance fees per itinerary.
Daily transportation on luxury bus or van with driver.
Personalized tour support.
Most meals (all breakfasts).
Commercial flight from Catania to Naples.
All airport transfers to/from airports/hotels.
Pricing: per person, single occupancy: $7,750. $800 single supplement.
EHE requires a deposit of $1,000 per person to confirm the trip. Final payment is due 90 days in advance of the trip.
Lodging is as follows; subject to change:
LOCATION AND LODGING (subject to change)
- Catania: Romano Palace Luxury
- Siracusa: Ortea Palace
- Paestum: Mec Paestum
- Amalfi: Amalfi Luna Convento
- Nettuno: Austura Palace
- Rome: Pantheon Iconic Rome Hotel, Autograph Collection

NOT INCLUDED

Flights to/from Europe
Alcohol

INTRIGUED BUT STILL HAVE QUESTIONS ABOUT TOURING ITALY?

Let’s schedule a conference call! We’d love to chat with you and answer any questions you may have.
Complete the contact form below and let’s set up a call.

19/09/2026 - 27/09/2026 12:00 am Italy in WWII: from Sicily to Rome