
2026 ITALY EXPERIENCE – FROM WAR TO WINE
May 01-07
Join us for a one-of-a-kind journey through southern Italy as we retrace the footsteps of Allied forces who fought their way up the rugged Italian peninsula during World War II. Over the course of seven days and six nights, you’ll stand where they stood, from the Mediterranean beaches where they landed, to the steep ridges and valleys where they fought some of the war’s most grueling battles.
We’ll walk the ground at Monte Cassino, one of the bloodiest and most pivotal battles of the Italian Campaign, and follow the hard road toward the liberation of Rome. Using firsthand accounts, photos, and maps, we’ll bring these powerful stories to life, connecting you directly to the heroes who made history here.
But this trip is also about experiencing the heart and soul of Italy. You’ll spend four days immersed in the campaign’s battlefield history, and three days enjoying Italy’s rich culture:
• Exclusive winery visits and tastings
• A visit to an active archaeological site
• World-class dining at locally loved restaurants
• Private experiences off the beaten path
Guests will stay in an authentic villa along the Mediterranean coast, with all ground transportation, breakfasts, dinners, and experiences included.
Come walk the trail of our WWII heroes, and experience the food, wine, and history of Italy like never before.
PRICE INCLUDES
• Led by U.S. Veterans, in support of Veterans
Experience WWII history alongside those who’ve served—100% of proceeds benefit U.S. Veterans.
• 6 nights at a Mediterranean villa
Stay in comfort with sea views, a private pool, bar, and classic Italian charm.
• 4 days of battlefield exploration
Walk the ground at Anzio, Monte Cassino, and the mountains that shaped the Italian Campaign.
• Exclusive access
Visit sites not open to the public, including the Monte Cassino Monastery, private vineyards, and commemorative events.
• Private winery tours & tastings
Go behind the scenes at southern Italy’s finest vineyards.
• Archaeological experience
Explore an active dig site and uncover Italy’s ancient past.
• All breakfasts & dinners included
Savor local cuisine at locally loved restaurants.
• Private transportation throughout
From arrival in Rome to every tour stop and back—travel in comfort.
• Rome pickup & drop-off
Airport, hotel, or another convenient location.
• Special commemorative gift
A keepsake to remember the journey and those who came before.




7 days & 6 nights
Single Traveler: $6,000
Couple: $9,500
DAILY ITINERARY
• Day 1: Arrival & Welcome
Private pickup in Rome and transfer to our Mediterranean villa. Enjoy an authentic Italian dinner and a relaxed trip overview with your veteran hosts.
• Day 2: The Italian Campaign Begins
Explore WWII landing sites along the coast and gain an overview of the Italian Campaign—where it began, how it evolved, and why it mattered.
• Day 3: The Winter Line & Mountain Warfare
Head into the mountains to learn about the brutal fighting along the Winter Line. Walk historic trails and gain insight into one of the most grueling phases of the campaign.
• Day 4: Monte Cassino
Visit the legendary Abbey of Monte Cassino and surrounding battlefield. Reflect on the 82nd anniversary of one of WWII’s fiercest and most pivotal battles.
• Day 5: Vineyards & Valor
Enjoy exclusive visits to local wineries with private tastings and behind-the-scenes access—blending history, heritage, and hospitality.
• Day 6: Culture & Connection
A curated day of Italian life—food, music, and hidden gems off the beaten path. Celebrate the culture that surrounded the soldiers’ struggle for liberation.
• Day 7: Farewell & Departure
Morning villa farewell followed by private return transportation to your preferred location in Rome.




ACOMODATION
All guests will stay in an iconic villa situated along the hills and mountains above the Mediterranean Sea.
The villa includes 7 guest suites, a bar, pool, private chef, and views for miles. This amazing symbol of Italian architecture and culture will make a fitting home base for our amazing Italian experience.

