ROAD TO ROME
Sept. 19-27, 2026

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.
$7,750 per person
End of the Expedition and Departures
Inclusions
Exclusions
Please note that the tour begins in Catania, Sicily and ends in Rome.
Pricing
Our rates are based on double occupancy:
Deposit and Final Payment
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.
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.

The HUSKY Landings and Initial Fights


The British Landings and Ancient Siracusa


Primosole, Magical Taormina, & Flight to Naples


Operation AVALANCHE, Magna Graecia, & Amalfi


The Battles at the GUSTAV Line and Cassino


Operation SHINGLE at Anzio and Nettuno


The Liberation of Rome

