Cruising Through Italy in a Ferrari Itinerary

hood of red sports car driving through countryside.
A 8 day trip to Italy & Vatican City 
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Ferrari conjures images of luxury and speed and combines modern fashion with a sense of history. Your customizable Italy itinerary will take you from Rome to Milan on a self-driving tour and allow you to experience the true beauty of Italian design from the art inside the Accademia Gallery to the cobbled lanes of medieval Siena. Discover Renaissance architecture in Pienza and the gilded coffered ceilings of the Map Room at the Vatican Museum. Treasure the remarkable countryside, bask in the prestige of a personal shopper in Milan, and indulge in the unique opportunity of driving a Ferrari through Italy. 

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General Information

Detailed Itinerary

Places Visited 

Rome, Florence, Milan, Bologna, Maranello, Siena, Chianti, San Casciano Bagni, Pienza 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Rome – Arrive in Rome and Explore the Piazzas of the Eternal City

The city of Rome embodies passion and history as lavish statues and fountains adorn the historical city center, and opulent villas overlook the pristine gardens. Narrow cobbled lanes lead to beautiful piazzas and allow locals and visitors alike to happen upon remnants of Ancient Rome. Your flight will land at Fiumicino Airport, and your private transfer will meet you upon arrival and escort you to your gorgeous villa located in the heart of the city. The traditional elegance of the past decorates the interior to bring traditional grace with modern luxury.

Your guide will greet you in the hotel lobby eager to lead you on an introductory tour of the Eternal City. The scent of fresh pasta dough emanates from restaurants hidden in the tapering alleys. As you stroll down the street, you will notice cobbles and dress makers working within the antique buildings. You will soon reach the Pantheon, the city’s most complete ancient structure, which was built in its current iteration in the 2nd century AD. The porch contains 16 granite columns adorned with Corinthian capitals.

Gold originally draped over the bronze doors, and once inside, you cannot help but notice the large hole in the dome. The feature remains the largest unreinforced concrete dome in the world, reaching a diameter of 142 feet, the same measurement as the distance between the floor and the top of the dome. The niches along the walls once held statues of Roman gods, and today contain the tombs of kings and famous Italians, including the Renaissance artist Raphael.

What’s Included: accommodation, airport transfer, tour

Day 2: Rome – Delight in a Private Tour of Vatican City and Rome’s Ancient Charm

The sunlight washes over the brickwork of the Castel Sant’Angelo, causing the ancient structure to glisten with gold over the banks of the Tiber River. The hidden alleys in the Trastevere district fill with the aromas of caramelized sugar, rich chocolate, and decadent espresso as drifting through the doors of the charming cafes. After an early breakfast, you will make your way to Vatican City, pausing to enjoy the marvelous pillars that border the street that leads to St. Peter’s Square. The boulevard manages to frame St. Peter’s Basilica, with the gilded top of the nearly 450-foot dome crowning the opulent edifice.

Workers broke ground on the Basilica in the early 16th century, finishing the structure more than 120 years later. The interior contains Michelangelo’s Pieta, along with the equestrian sculpture The Vision of Constantine, which was crafted in the 17th century by Bernini. Your guide will greet you at the obelisk located at the heart of the square before leading you into the heart of papal treasures on display in the museum. The polished halls of the galleries will flicker with natural light that pours in through the large windows.

The galleries offer insight into the lavish lifestyles of former popes, along with their personal aesthetic in art and comforts. You will reach the Gallery of Maps and wander beneath the 16th-century frescoes that depict Italian cities and the countryside. Geographical features add texture to the walls and ceiling, including images of the Apennine Mountains and the Tyrrhenian Sea. The coffered ceilings shimmer with gilded frames, demarking 40 separate panels. It will soon be easy to see how much the topography and city designs have changed over the past half-millennium.

What’s Included: accommodation, tour, breakfast

Day 3: San Casciano Bagni – Revel in a Scenic Ferrari Drive and Tour of Pienza

The Mille Miglia was named for its test of endurance that spans 1,000 Roman miles, with participants traveling between Brescia to Rome and back again. In the morning, you will enjoy the aroma of freshly roasted coffee as it blends with the scent of orange zest that emanates from the orchard in the villa’s private garden. After breakfast, your guide will introduce you to the power, prestige, and comforts of a Ferrari California, known as a touring sports car. The sleek design hides a 4.3-litre V8 engine, and you will hear the power revving from the engine.

The car will feel like its own work of art as it contrasts with the ancient wonders of the Colosseum and the Roman Forum with a mixture of modern science, vintage style, and the ability to accelerate from zero to 62 miles per hour in under four seconds. Your professional driver will offer you a chance to practice driving the Ferrari before venturing out along the Mille Miglia, and the smooth leather wheel will fit perfectly in your hands.

The wind will pass gently over the car, and you will feel as though you are gliding over the road. Take to the streets and leave Rome behind en route to gorgeous San Casciano Bagni, taking in the spectacular panoramas of the Lazio countryside as you travel. Stop in the town of Pienza, a small town in Val d’Orcia, Tuscany. Medieval walls continue to border the town along the cypress and oak trees, as Pope Pius II helped reorganize the medieval streets into the ideal Renaissance town. Situated atop the Tuscan hills and adorned with a sensational Cathedral tower rising above the rooftops like a beacon, you will see that he succeeded.

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

Day 4: Florence – Tour Gorgeous Siena and Stunning Chianti en route to Florence

The bakery fills the town of San Casciano Bagni with the aroma of buccellato, a sweet and soft cake brushed with sugar and egg often found in the shape of a donut. The cypress trees, emblematic of the Tuscan landscape, surrounds the quiet medieval village and leads to the vineyards that blanket the rolling hills of the countryside. You will step into your Ferrari after breakfast and make your way towards the Renaissance city, stopping first in the town of Siena, the former rivaling powerhouse to Florence. The picturesque streets and walls overtake the hills, preserving the artistry and architecture of the 13th and 14th centuries. Cathedrals and palaces shimmer with brick and red clay features and the 14th century walls lead to the imposing Porta Romana, the original gateway into Old Town.

Siena is known for holding the famous Palio races twice a year inside the Piazza del Campo. Facades curve to accommodate the unique design of the piazza. The Palazzo Pubblico features the graceful Torre del Mangia, which reaches a height of nearly 335 feet above the cobbled plaza below. The narrow brick shaft supports the travertine brackets and battlements as the aroma of vanilla and chocolate emanates from the celebrated gelateria found around the city. The majestic 13th-century Gothic figure of the Cathedral dominates Piazza del Duomo with three-arched doorways, mosaics, and black and white stripes adorning the facade.

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

Day 5: Bologna – Enjoy a Florence Guided Tour and Travel the Passo della Raticosa

Florence resembles a small city but displays its prominent beauty along the banks of the Arno River with pride. The Ponte Vecchio Bridge continues to stretch over the waterway featuring medieval shops dedicated to gold and jewelry, while bakeries hide amongst the narrow cobblestone alleyways and turn the historic city center into a labyrinth of enchanting aromas. Cafes set out their tables along the narrow streets and open piazzas to provide distinctive views of the historical facades of  the surrounding structures and the ever-present peak of the Duomo’s dome. Your guide will greet you after breakfast and take you on a fabulous walking tour of the Renaissance city, beginning at the Cathedral.

The green and white marble façade feature embellishments of towering arched doorways and intricate statues. The interior carries the aroma of frankincense and myrrh from the morning’s observances. Candles flicker along the sides of the nave beneath the Gothic arches and stone pillars, and 44 windows allow natural light to spill into the gallery, including the three rose windows designed by Lorenzo Ghiberti. Stand beneath the center of Brunelleschi’s dome, where 88 reliefs swirl around the interior and embellish the enormity of the brick feature. You can venture up to the top of the dome, traversing more than 450 steps, for a view of the Cathedral from above, along with an unfettered panorama of Florence and the Tuscan countryside before you return to the Ferrari and ride north to Bologna.

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

Day 6: Milan – Relish a Balsamic Tasting and Visit the Ferrari Gallery in Maranello

The aroma of freshly baked brioche drifts beneath the historical arcades of Bologna. Boutique shops fill antique buildings and brickwork frames the cafes as they set out their tables along the cobbled streets. The dramatic bronze statue of Neptune adorns the center of Piazza del Nettuno and the water trickles down into the waiting pool and fills the square with a serene soundtrack. After breakfast, you will return to your Ferrari and head out into the countryside of Emilia-Romagna to follow the road that leads north to Milan. The aroma of cedar and oak emanates from the forests and hills around the region, and you will stop at an acetaia, a small factory that produces balsamic vinegar.

Your guide will lead you through the estate and showcase the strict manner in which the vinegar is produced. The traditions have been passed down through generations and continue to cook down red and white grapes after the wine harvest. The reduction sits in an oak barrel, and yearly the vinegar is transferred into various types of wood barrels, including cherry and juniper which add layers of different flavors and age for up to 25 years. The cellars in which the barrels rest are cool, with the stone walls keeping the heat away. Your guide will offer you a tasting of the balsamic produced on the property. A tart and sweet flavor that blends chocolate and strawberries will linger on your palette. You will then continue to Maranello to visit the museum dedicated to displaying the evolution of Ferrari’s design of the car’s interior and exterior. 

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

Day 7: Milan – Tour Historical Milan and Enjoy a Personalized Shopping Experience

The morning light will wash through the glass dome of the Vittorio Emanuele II Gallery. The mosaic floors of the 19th-century edifice continue to accentuate the grace and style of the shopping arcades and boutique shops that are framed by antique filigree. Your guide will greet you in the lobby and lead you on an encompassing tour of the fashion capital of Italy, from the medieval towers of the Sforza Castle to the staggering amount of statues that adorn the Gothic cathedral at the heart of the city center.

Shops offer graceful window displays that line the streets of the city and provide color amongst the seasoned stone structures. Your guide will begin your tour at the Santa Maria delle Grazie, an unassuming brick church erected in the late 15th century. The six-sided dome will capture your attention as the embodiment of early Renaissance style. The nave contains the subtle aroma of frankincense as you make your way into the refectory of the former Dominican monastery to view Leonardo da Vinci’s renowned work The Last Supper.

The painting depicts the final meal of Jesus and the Apostles on a plank of wood 181 inches by 346 inches. The presence of the painting is palpable in the atmosphere in its size and reputation with your nearly private view. After touring the beauty of the city’s artistry, you will meet with a private fashion consultant eager to lead you through the various shopping districts of the city, from Via Borgospesso to Via Montenapoleone, for a private shopping experience inside Italy’s fashion capital.

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

Day 8: Milan – Depart for Home

The artistic and bohemian ambiance of the Brera district returns in the morning. The narrow alleys and vibrant shops seem worlds away from the Gothic features of the Cathedral when in fact, the district neighbors the Cathedral to the north. Art galleries feature modern painters and sculptors with cafes setting out flowers on their tables for a touch of cozy atmosphere. A bronze statue of Napoleon depicted as the Roman god of war adorns the courtyard of the Palazzo Brera in the heart of the neighborhood. Although you have already turned in your Ferrari, the thrills of your drives from Rome to Milan remain with you. Your private transfer will meet you at your hotel in the heart of the city and escort you to Malpensa 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.