In the Footsteps of Italian History Tour: From Antiquity to Contemporary

A 8 day trip to Italy 
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The Second World War forever changed Europe, from Britain in the north to Sicily in the south, leaving trails in the form of stories now illuminated in Italy, leading you from Rome to the Amalfi Coast. Your custom tailored tour brings history to life, from the Italian beaches on which the allies landed to the former German Embassy in Rome that the SS turned into a jail, imprisoning members of the Italian Resistance. From occupation to liberation, you will explore and discover the unique stories of Italy preserved on the shores, in the hills, and exhibited in local museums. 

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General Information

Detailed Itinerary

Places Visited 

Rome, Anzio, Montecassino, Naples, Positano, Amalfi, Ravello, Vietri sul Mare, Conca dei Marini 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Rome – A World of the Classics

Rome is a city that has watched the world change for more than 2,000 years, evolving with new times, new kingdoms, and new ways of thinking. With each large-scale change in the world, the city of Rome remains constant, giving it the nickname the “Eternal City.” Your flight lands in Fiumicino International Airport. Your private transfer meets you at baggage claim and escorts you into the historic city center to your hotel located in a renovated 19th-century palace. The marble bath and large terrace provide perfect introductions into the beauty of Rome’s elegant past with a hint of the types of lavish embellishments the Roman aristocracy enjoyed.

After settling into the comforts of your room and the view from your balcony overlooking the Seven Hills of Rome, you meet your private guide in the hotel lobby for an introductory tour. The iconic images of Rome come to life, beginning with the Trevi Fountain. The 18th-century adornment stands on the back of Palazzo Poli with a height of 86 feet tall and more than 160 feet wide. The sound of trickling water emanates from the widespread waterfall falling into the waiting, iridescent pool. Oceanus stands at the center of the fountain surveying the water atop his shell chariot. People stand with their backs to the fountain and throw coins over their left shoulder. They listen for the splash of the coin hitting the water, which, according to legend, means the person will return to Rome.

What’s Included: transfer, tour, accommodation

Day 2: Rome – Partisans and Troops

In the morning, the aroma of fresh espresso emanates from the cafes, blending with the scent of baking brioches drifting out of the bakeries. The flower vendors in Campo de’Fiori offer bundles of hydrangeas, carnations, roses, and sunflowers to mix a touch of nature in the expansive cobblestone streets and stone structures of the ancient urban city. After breakfast, your guide meets you at the hotel, ready to lead you through a day dedicated to Italian partisans who fought in preparation for the coming Allied troops.

The Museum of the Liberation of Rome is located on Via Tasso, close to the celebrated basilica of St. John Lateran. The museum is dedicated to Rome’s history under German occupation during World War II, along with the city’s subsequent liberation. The museum opened in the 1950s inside what was originally the German Embassy beginning in the 1930s. The grounds maintain their significance, not only as the former SS headquarters in Rome, but also as a place in which the Nazi high command imprisoned, interrogated, and even tortured members of the Italian resistance.

The gallery has preserved graffiti scrawled by inmates on the cell walls, offering insight into the mindset of those trapped inside the building. The gallery has a quiet, stoic ambiance decorated with photos, documents, and improvised weapons. The SS converted the former kitchen of the embassy into a cell to contain more prisoners during the height of the war. Cell four has a moratorium to 14 prisoners taken by the SS after the Germans retreated from Rome, only to be executed later at La Storta.

What’s Included: breakfast, tour, accommodation

Day 3: Anzio – Landings and Liberations

In the morning, painters make their way to the Baroque square of Piazza Novara, excited to capture the palaces and fountains in the right light of day. The cafes set out tables and chairs in view of the intimate details of the Fountain of the Four Rivers. Cafes fill with locals eager to drink their espresso before heading to work. After breakfast, you meet your private transfer and guide in the lobby and travel south to Anzio, a former Roman fishing port. Boats wade in the marina with fishermen returning from the open sea with full of prawn, squid, and branzino.

The coastal town has a significant attachment to military achievements dating as far back as Coriolanus’s rebellion against Rome. Emperor Nero was born in the town and the ruins of his former villa remain visible on the low cliffs overlooking the water. The briny and semi-sweet aroma of the sea sweeps across the promenade with the refreshing breeze. The Allied troops landed on the beaches of Anzio in January of 1944. Although much of the town was rebuilt after World War II, the streets and buildings maintain their atmosphere of a sleepy, antique fishing town decorated with colorful facades. Grottos border the sandy beach on in which the battered allies sought refuge after landing on the shoreline.

You reach the Enter into the Anzio Beachhead Museum, which was opened in the early 1990s on the fiftieth anniversary of the landings. The galleries overtake Villa Adele in the heart of town. The main gallery exhibits photographs, uniforms, and artifacts, including personal photos donated by American and British soldiers who participated in the initial battle to take Italy. After exploring the beauty and history of Anzio, you venture to the marina and board a boat for a sightseeing cruise along X-ray Beach, on which American troops landed. The beach is closed to the public, as it is now an Italian military shooting range. You can look into the crystal clear Mediterranean to see the outline of a landing craft sunk during the battle in 1944. 

What’s Included: breakfast, tour, transfer, accommodation

Day 4: Montecassino – In the Air of Paratroopers

In the morning, the scent of fresh brioche blends with the sea breeze. Hydrofoils and ferries make their first crossing for the day to nearby islands. The villas surrounding the seaside glow against the pebbled shores and boulders set against the crystalline indigo Mediterranean. After breakfast, your private transfer meets you at the hotel and escorts you to Montecassino, an abbey situated atop a hill overlooking the evergreen trees on the valley floor and the Lazio mountain summits in the distance. Elements of the first settlement on the hilltop date back to the 5th century BC, with the abbey’s foundations first lain in the 11th century.

Your guide points out the Gustav Line, a German military fortification designed to defend Western Italy around the town of Cassino. The abbey was a coveted position due to its placement along the Gustav Line and its aerial view over the landscape, giving the German military plenty of time to notice potential attackers. The battles of Montecassino were fought with the intention of the allies breaking through the German fortifications to reach Rome. The abbey, located on the hilltop, increased the woes of the allied forces due to its strategic positioning.

The scars of the abbey from the February bombing in 1944 remain, but the majority of the impressive structure continues to stand to overlook the surrounding valley. The German paratrooper division hid amongst the rubble and continued to fight the allied forces. The history is palpable in the halls of the abbey, with the stone telling an ancient and contemporary history with a vibrant present. The cloister offers a magnificent perspective of the lavish courtyard with arches framing the view to the mountains on the horizon.

What’s Included: breakfast, tour, transfer, accommodation

Day 5: Positano – History in the Halls

The striking figure of the Rocca Janula Fortress stands on the hillside overlooking the edges of the town of Cassino. The white stone glints with the sunlight, contrasting the lush greenery growing along the fortress foundation. Your private transfer meets you at the hotel and escorts you south towards Naples, stopping at the Palace of Caserta for an introduction to the opulence of the Kingdom of Naples, along with the German appropriation of the kingdom’s grandeur during its occupation in World War II. The palace had housed the Italian Air Force Academy from 1923 to 1943 before the Germans signed the terms of unconditional surrender inside the halls of the palace in 1945. The grounds encompass more than 2.5 million square feet over five stories.

The throne room has a gilded outline with a vibrant fresco stretching across the center of the ceiling. A golden state above the throne adds to the opulent décor and former prestige of the Bourbon kings. The elegant interior and intricate artwork highlight the mastery of the baroque period, which is adorned with a wide central dome embellished with frescoes, stuccoes, and reliefs. The thrill of standing in the galleries fit for royalty pales in the excitement you have for standing in the room in which the Germans adhered to an unconditional surrender to Allied forces. The grandeur of the palace grounds leads you to the nearly 300 acres of gardens, crafted to inspire visitors with a series of rushing waterfalls and trickling fountains.

What’s Included: breakfast, tour, transfer, accommodation

Day 6: Positano – Italy’s Former Capital

In the morning, you wake up in a gorgeous 18th-century palace renovated as a luxurious hotel overlooking the steep slopes of the maritime mountains dropping into the Tyrrhenian Sea. At breakfast, you indulge in a frothy cappuccino and enjoy the view of the narrow cobblestone streets of Positano. Pastel homes brighten the verdant hillside decorated with vines, olive orchards, and citrus groves. The aroma of lemons and oranges brings a zesty hint to the seaside air. Your private guide meets you in the hotel lobby, ready to lead you along the scenic roadway of the Amalfi Coast. The turquoise water shines beneath the vast stretch of sunlight.

Towns ascend the hillsides and border the shoreline with pebbled beaches and small marinas. The dome of the cathedral in the town of Vietri sul Mare glints with glossy mosaic tiles. The same mosaics adorn the facades of boutique shops and restaurants around town, decorating the lanes and stairways. Ceramic workshops open their doors to visitors to showcase the long history of the artwork in town with roots dating back to the 15th century. The scent of grilled branzino garnished with fresh squeezed lemon emanates from hidden restaurants tucked into the alleyways. When you reach Salerno, the largest city on the gulf, you have arrived at the end of what is considered the Amalfi Coast.

The city has Etruscan origins, along with a history of a Roman settlement beginning in the 2nd century BC. The city acted as an important landing for Allied troops during the Second World War, suffering heavy damage before the troops claimed victory. Salerno also acted as the capital of Italy for a short time, housing King Victor Emmanuel III before the liberation of Rome. The seaside promenade offers the possibility for a long stroll beside the water amidst the swirling aromas of the Mediterranean, grilling seafood, and sweet gelato.

What’s Included: breakfast, tour, accommodation

Day 7: Positano – Leisure on the Coastline

Positano returns to quiet life in the morning with the fishermen returning to shore. Their boats wade in the marina near the small seaside walkway. Boutique shops fill their display windows with elaborate scenes of posing mannequins or colorful fruit-themed dishes and tableware. In the cobblestone alley of Via Pasitea stands a store with a traditional cobbler happy to make sandals while you wander around the cobblestone streets of Positano. After breakfast, the day is yours to enjoy the wonders of the Amalfi Coast, from exploring the villages of the hills or shoreline in more depth to venturing to Naples to visit the Archeological Museum.

For those enthusiastic about history, you can make your way around the Bay of Naples to the entrance of the Pompeii. Your guide meets you before entering the grounds of the ancient site preserved in ash and pumice from the eruption of Mount Vesuvius in 79 AD. The aroma of rich soil remains prevalent around the former Roman port city. The main road leads you first to the Roman Forum, the center of civil and religious life. Columns continue to line the streets and frame the nearly 10-foot tall platform that once supported the Temple of Jupiter.

The granary and former fish market once bordered the Forum as well. On the main streets of the excavated neighborhoods, you pass a home with a stove near the doorway. A fresco continues to decorate the wall. The countertop represents a fast-food establishment where passersby could buy and consume a hot meal quickly. The Amphitheater was erected in 80 BC and could hold up to 12,000 spectators. It remains the oldest surviving Roman amphitheater in the world.  The summit of Mount Vesuvius remains in view of the city, looming with a perfect conical peak in the background of the city it once encased.

What’s Included: breakfast, accommodation

Day 8: Positano – Leaving History Behind

In the morning, you can walk through the botanic garden tucked inside the hills and hidden above the sundrenched lanes of Positano. Hydrangeas blossom beneath dangling bougainvillea, contrasting the dramatic façade of the antique palace. At breakfast, you indulge in the bittersweet flavor of a freshly brewed cappuccino topped with a frothy layer of foam. You have grown accustomed to the simple pleasures of Italian culture, from basking in the taste of morning coffee to delighting in the flakey outer layer of a freshly baked brioche. The sweet scent of the flowers overtakes the citrus aromas of orange and lemon. Your private transfer meets you in the hotel lobby and escorts you to Naples International Airport for your flight home.

What’s Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.