Home » Luxury Driving journeys » Milano – Rome
Experience the road with total peace of mind – join an intimate group guided by a professional, with luxury cars and full-service support. Every detail is taken care of, so you can simply live the moment
Take the wheel of a high-performance luxury car and embark on an extraordinary driving journey through the soul of Italy.
From the vibrant start in Milan and the legendary Food Valley of Bologna, through the winding, historic passes of the Apennines and the sun-drenched vineyards of Tuscany and Chianti, every road tells a story. Along the way, explore medieval towers, steaming natural hot springs, and enchanting hilltop towns before your grand finale in the Eternal City.
Along the journey, enjoy refined boutique accommodations, world-class gastronomy, and exclusive moments crafted for those who seek the ultimate Italian experience behind the wheel.
We begin the journey at the hotel with the handover of the luxury car and a driving briefing before heading south toward Italy’s legendary Food Valley. Our first stop is a traditional Parmigiano-Reggiano dairy near Parma or Modena, where we enjoy a morning tour to witness the fascinating production and aging process of this iconic cheese.
Next, we continue to a historic castle or local winery in the rolling hills of Emilia-Romagna for an afternoon tasting of fine local wines, including high-quality Lambrusco. In the evening, we arrive in vibrant Bologna for a walking tour of the historic center—taking in the lively Piazza Maggiore and the famous Two Towers (Le Due Torri)—before settling in for a classic, hearty Emilian dinner.
Morning tour and tasting at a traditional Parmigiano-Reggiano dairy
Afternoon winery visit and wine tasting in the hills of Emilia-Romagna
Evening walking tour of Piazza Maggiore and the Two Towers in Bologna
Scenic drive through the heart of the Emilia-Romagna region
We begin the journey at the hotel with the handover of the luxury car and a driving briefing before heading south toward Italy’s legendary Food Valley. Our first stop is a traditional Parmigiano-Reggiano dairy near Parma or Modena, where we enjoy a morning tour to witness the fascinating production and aging process of this iconic cheese.
Next, we continue to a historic castle or local winery in the rolling hills of Emilia-Romagna for an afternoon tasting of fine local wines, including high-quality Lambrusco. In the evening, we arrive in vibrant Bologna for a walking tour of the historic center—taking in the lively Piazza Maggiore and the famous Two Towers (Le Due Torri)—before settling in for a classic, hearty Emilian dinner.
Morning tour and tasting at a traditional Parmigiano-Reggiano dairy
Afternoon winery visit and wine tasting in the hills of Emilia-Romagna
Evening walking tour of Piazza Maggiore and the Two Towers in Bologna
Scenic drive through the heart of the Emilia-Romagna region
We set off from Bologna to conquer the legendary Passo della Futa (SS65), enjoying an exhilarating, winding drive through the Apennine Mountains along a historic route of the famous Mille Miglia race, complete with a coffee stop at the mountain peak.
Next, we descend toward Florence for a breathtaking panoramic view of the city and its magnificent Duomo from Piazzale Michelangelo. In the afternoon, we continue along the world-renowned Chianti Wine Road (SS222 - Via Chiantigiana), driving through rolling hills and endless vineyards before stopping to explore charming towns like Greve in Chianti or Radda. We end the day checking into a refined countryside hotel in the heart of Chianti for a relaxed, authentic Tuscan evening.
Driving the legendary winding pass of Passo della Futa (SS65) – historic Mille Miglia route
Coffee stop at the peak of the Apennine mountain pass
Panoramic views of Florence and the Duomo from Piazzale Michelangelo
Scenic drive along the famous Chianti Wine Road (SS222 - Via Chiantigiana)
Exploration of picturesque Tuscan villages
We set off from Bologna to conquer the legendary Passo della Futa (SS65), enjoying an exhilarating, winding drive through the Apennine Mountains along a historic route of the famous Mille Miglia race, complete with a coffee stop at the mountain peak.
Next, we descend toward Florence for a breathtaking panoramic view of the city and its magnificent Duomo from Piazzale Michelangelo. In the afternoon, we continue along the world-renowned Chianti Wine Road (SS222 - Via Chiantigiana), driving through rolling hills and endless vineyards before stopping to explore charming towns like Greve in Chianti or Radda. We end the day checking into a refined countryside hotel in the heart of Chianti for a relaxed, authentic Tuscan evening.
Driving the legendary winding pass of Passo della Futa (SS65) – historic Mille Miglia route
Coffee stop at the peak of the Apennine mountain pass
Panoramic views of Florence and the Duomo from Piazzale Michelangelo
Scenic drive along the famous Chianti Wine Road (SS222 - Via Chiantigiana)
Exploration of picturesque Tuscan villages
We begin our morning driving through the heart of Tuscany to the famous hilltop town of San Gimignano, renowned for its striking medieval stone towers and a stop to taste award-winning artisanal gelato in the historic square.
Next, we continue to Siena to admire the shell-shaped wonder of Piazza del Campo and the magnificent Gothic cathedral. In the afternoon, we enjoy a scenic drive eastward into Umbria, arriving in Perugia for an evening stroll along the lively pedestrian Corso Vannucci and a visit to the fascinating underground fortress of Rocca Paolina, before settling in for a wonderful Umbrian dinner.
Morning drive through the Tuscan landscape to San Gimignano
Exploring the medieval towers and award-winning gelato in San Gimignano
Visit to Siena’s iconic Piazza del Campo and Gothic cathedral
Scenic drive from Tuscany into the green heart of Umbria
Evening stroll along Corso Vannucci and exploration of Rocca Paolina in Perugia

We begin our morning driving through the heart of Tuscany to the famous hilltop town of San Gimignano, renowned for its striking medieval stone towers and a stop to taste award-winning artisanal gelato in the historic square.
Next, we continue to Siena to admire the shell-shaped wonder of Piazza del Campo and the magnificent Gothic cathedral. In the afternoon, we enjoy a scenic drive eastward into Umbria, arriving in Perugia for an evening stroll along the lively pedestrian Corso Vannucci and a visit to the fascinating underground fortress of Rocca Paolina, before settling in for a wonderful Umbrian dinner.
Morning drive through the Tuscan landscape to San Gimignano
Exploring the medieval towers and award-winning gelato in San Gimignano
Visit to Siena’s iconic Piazza del Campo and Gothic cathedral
Scenic drive from Tuscany into the green heart of Umbria
Evening stroll along Corso Vannucci and exploration of Rocca Paolina in Perugia

We start the day by visiting the majestic Marmore Falls (Cascata delle Marmore), one of Europe’s highest man-made waterfalls, perfectly timed to experience the stunning morning water release.
Next, we drive toward the breathtaking Civita di Bagnoregio, famously known as the "Dying Town," perched dramatically on a crumbling tuff cliff and accessible only via a striking pedestrian bridge. In the afternoon, we continue our journey into the enchanting landscape of southern Tuscany, arriving by late afternoon at the famous thermal hot springs of Saturnia (Cascate del Mulino) for a relaxing soak in the steaming turquoise natural pools before checking into a serene boutique hotel in the Maremma region.
Morning viewing of the spectacular Marmore Falls
Visit to the dramatic cliffside village of Civita di Bagnoregio
Afternoon scenic drive through southern Tuscany
Relaxing soak in the natural thermal waterfalls of Saturnia (Cascate del Mulino)
Overnight stay in the picturesque Maremma countryside

We start the day by visiting the majestic Marmore Falls (Cascata delle Marmore), one of Europe’s highest man-made waterfalls, perfectly timed to experience the stunning morning water release.
Next, we drive toward the breathtaking Civita di Bagnoregio, famously known as the "Dying Town," perched dramatically on a crumbling tuff cliff and accessible only via a striking pedestrian bridge. In the afternoon, we continue our journey into the enchanting landscape of southern Tuscany, arriving by late afternoon at the famous thermal hot springs of Saturnia (Cascate del Mulino) for a relaxing soak in the steaming turquoise natural pools before checking into a serene boutique hotel in the Maremma region.
Morning viewing of the spectacular Marmore Falls
Visit to the dramatic cliffside village of Civita di Bagnoregio
Afternoon scenic drive through southern Tuscany
Relaxing soak in the natural thermal waterfalls of Saturnia (Cascate del Mulino)
Overnight stay in the picturesque Maremma countryside

We begin our final day driving from southern Tuscany toward the lush hills of the Castelli Romani. Our first stop is the boutique village of Nemi, perched gracefully above a volcanic lake and famous for its wild strawberries and charming local bakeries.
Next, we continue to Castel Gandolfo to enjoy stunning views over Lake Albano, the historic papal summer residence, and a relaxing coffee in the picturesque main piazza. In the afternoon, we make our final elegant drive into the heart of Rome for the luxury car handover and check-in at a fine hotel, bringing an unforgettable driving journey to a close.
Morning visit to the charming lakeside village of Nemi
Views of Lake Albano and coffee in the papal town of Castel Gandolfo
Final elegant drive into the heart of Rome
We begin our final day driving from southern Tuscany toward the lush hills of the Castelli Romani. Our first stop is the boutique village of Nemi, perched gracefully above a volcanic lake and famous for its wild strawberries and charming local bakeries.
Next, we continue to Castel Gandolfo to enjoy stunning views over Lake Albano, the historic papal summer residence, and a relaxing coffee in the picturesque main piazza. In the afternoon, we make our final elegant drive into the heart of Rome for the luxury car handover and check-in at a fine hotel, bringing an unforgettable driving journey to a close.
Morning visit to the charming lakeside village of Nemi
Views of Lake Albano and coffee in the papal town of Castel Gandolfo
Final elegant drive into the heart of Rome
• Driving a variety of high-end supercars
• Accommodation in boutique and five-star hotels across Italy
• Meals at gourmet restaurants, as well as traditional and authentic local cuisine
• Driving tours through some of the most beautiful roads and landscapes in the world
• Fuel & refueling service | Private parking
• Flights
• Traffic fines and other reports
• Refundable security deposit up to €3,500 – €6,500 (depending on the car) in case of damages
• Driver’s license, local and international
• A valid credit card with an available credit limit sufficient to cover the required security deposit
• Passports and ID documents
• Recommended: Phone chargers and cables
Travel on your own terms – with the full support of luxury planning. We craft your perfect route, recommend five-star hotels, and provide smart Maps links – giving you a seamless, independent journey without sacrificing elegance or ease.
Take the wheel of a high-performance luxury car and embark on an extraordinary driving journey through the soul of Italy.
From the vibrant start in Milan and the legendary Food Valley of Bologna, through the winding, historic passes of the Apennines and the sun-drenched vineyards of Tuscany and Chianti, every road tells a story. Along the way, explore medieval towers, steaming natural hot springs, and enchanting hilltop towns before your grand finale in the Eternal City.
Along the journey, enjoy refined boutique accommodations, world-class gastronomy, and exclusive moments crafted for those who seek the ultimate Italian experience behind the wheel.
We begin the journey at the hotel with the handover of the luxury car and a driving briefing before heading south toward Italy’s legendary Food Valley. Our first stop is a traditional Parmigiano-Reggiano dairy near Parma or Modena, where we enjoy a morning tour to witness the fascinating production and aging process of this iconic cheese.
Next, we continue to a historic castle or local winery in the rolling hills of Emilia-Romagna for an afternoon tasting of fine local wines, including high-quality Lambrusco. In the evening, we arrive in vibrant Bologna for a walking tour of the historic center—taking in the lively Piazza Maggiore and the famous Two Towers (Le Due Torri)—before settling in for a classic, hearty Emilian dinner.
Morning tour and tasting at a traditional Parmigiano-Reggiano dairy
Afternoon winery visit and wine tasting in the hills of Emilia-Romagna
Evening walking tour of Piazza Maggiore and the Two Towers in Bologna
Scenic drive through the heart of the Emilia-Romagna region
We begin the journey at the hotel with the handover of the luxury car and a driving briefing before heading south toward Italy’s legendary Food Valley. Our first stop is a traditional Parmigiano-Reggiano dairy near Parma or Modena, where we enjoy a morning tour to witness the fascinating production and aging process of this iconic cheese.
Next, we continue to a historic castle or local winery in the rolling hills of Emilia-Romagna for an afternoon tasting of fine local wines, including high-quality Lambrusco. In the evening, we arrive in vibrant Bologna for a walking tour of the historic center—taking in the lively Piazza Maggiore and the famous Two Towers (Le Due Torri)—before settling in for a classic, hearty Emilian dinner.
Morning tour and tasting at a traditional Parmigiano-Reggiano dairy
Afternoon winery visit and wine tasting in the hills of Emilia-Romagna
Evening walking tour of Piazza Maggiore and the Two Towers in Bologna
Scenic drive through the heart of the Emilia-Romagna region
We set off from Bologna to conquer the legendary Passo della Futa (SS65), enjoying an exhilarating, winding drive through the Apennine Mountains along a historic route of the famous Mille Miglia race, complete with a coffee stop at the mountain peak.
Next, we descend toward Florence for a breathtaking panoramic view of the city and its magnificent Duomo from Piazzale Michelangelo. In the afternoon, we continue along the world-renowned Chianti Wine Road (SS222 - Via Chiantigiana), driving through rolling hills and endless vineyards before stopping to explore charming towns like Greve in Chianti or Radda. We end the day checking into a refined countryside hotel in the heart of Chianti for a relaxed, authentic Tuscan evening.
Driving the legendary winding pass of Passo della Futa (SS65) – historic Mille Miglia route
Coffee stop at the peak of the Apennine mountain pass
Panoramic views of Florence and the Duomo from Piazzale Michelangelo
Scenic drive along the famous Chianti Wine Road (SS222 - Via Chiantigiana)
Exploration of picturesque Tuscan villages
We set off from Bologna to conquer the legendary Passo della Futa (SS65), enjoying an exhilarating, winding drive through the Apennine Mountains along a historic route of the famous Mille Miglia race, complete with a coffee stop at the mountain peak.
Next, we descend toward Florence for a breathtaking panoramic view of the city and its magnificent Duomo from Piazzale Michelangelo. In the afternoon, we continue along the world-renowned Chianti Wine Road (SS222 - Via Chiantigiana), driving through rolling hills and endless vineyards before stopping to explore charming towns like Greve in Chianti or Radda. We end the day checking into a refined countryside hotel in the heart of Chianti for a relaxed, authentic Tuscan evening.
Driving the legendary winding pass of Passo della Futa (SS65) – historic Mille Miglia route
Coffee stop at the peak of the Apennine mountain pass
Panoramic views of Florence and the Duomo from Piazzale Michelangelo
Scenic drive along the famous Chianti Wine Road (SS222 - Via Chiantigiana)
Exploration of picturesque Tuscan villages
We begin our morning driving through the heart of Tuscany to the famous hilltop town of San Gimignano, renowned for its striking medieval stone towers and a stop to taste award-winning artisanal gelato in the historic square.
Next, we continue to Siena to admire the shell-shaped wonder of Piazza del Campo and the magnificent Gothic cathedral. In the afternoon, we enjoy a scenic drive eastward into Umbria, arriving in Perugia for an evening stroll along the lively pedestrian Corso Vannucci and a visit to the fascinating underground fortress of Rocca Paolina, before settling in for a wonderful Umbrian dinner.
Morning drive through the Tuscan landscape to San Gimignano
Exploring the medieval towers and award-winning gelato in San Gimignano
Visit to Siena’s iconic Piazza del Campo and Gothic cathedral
Scenic drive from Tuscany into the green heart of Umbria
Evening stroll along Corso Vannucci and exploration of Rocca Paolina in Perugia

We begin our morning driving through the heart of Tuscany to the famous hilltop town of San Gimignano, renowned for its striking medieval stone towers and a stop to taste award-winning artisanal gelato in the historic square.
Next, we continue to Siena to admire the shell-shaped wonder of Piazza del Campo and the magnificent Gothic cathedral. In the afternoon, we enjoy a scenic drive eastward into Umbria, arriving in Perugia for an evening stroll along the lively pedestrian Corso Vannucci and a visit to the fascinating underground fortress of Rocca Paolina, before settling in for a wonderful Umbrian dinner.
Morning drive through the Tuscan landscape to San Gimignano
Exploring the medieval towers and award-winning gelato in San Gimignano
Visit to Siena’s iconic Piazza del Campo and Gothic cathedral
Scenic drive from Tuscany into the green heart of Umbria
Evening stroll along Corso Vannucci and exploration of Rocca Paolina in Perugia

We start the day by visiting the majestic Marmore Falls (Cascata delle Marmore), one of Europe’s highest man-made waterfalls, perfectly timed to experience the stunning morning water release.
Next, we drive toward the breathtaking Civita di Bagnoregio, famously known as the "Dying Town," perched dramatically on a crumbling tuff cliff and accessible only via a striking pedestrian bridge. In the afternoon, we continue our journey into the enchanting landscape of southern Tuscany, arriving by late afternoon at the famous thermal hot springs of Saturnia (Cascate del Mulino) for a relaxing soak in the steaming turquoise natural pools before checking into a serene boutique hotel in the Maremma region.
Morning viewing of the spectacular Marmore Falls
Visit to the dramatic cliffside village of Civita di Bagnoregio
Afternoon scenic drive through southern Tuscany
Relaxing soak in the natural thermal waterfalls of Saturnia (Cascate del Mulino)
Overnight stay in the picturesque Maremma countryside

We start the day by visiting the majestic Marmore Falls (Cascata delle Marmore), one of Europe’s highest man-made waterfalls, perfectly timed to experience the stunning morning water release.
Next, we drive toward the breathtaking Civita di Bagnoregio, famously known as the "Dying Town," perched dramatically on a crumbling tuff cliff and accessible only via a striking pedestrian bridge. In the afternoon, we continue our journey into the enchanting landscape of southern Tuscany, arriving by late afternoon at the famous thermal hot springs of Saturnia (Cascate del Mulino) for a relaxing soak in the steaming turquoise natural pools before checking into a serene boutique hotel in the Maremma region.
Morning viewing of the spectacular Marmore Falls
Visit to the dramatic cliffside village of Civita di Bagnoregio
Afternoon scenic drive through southern Tuscany
Relaxing soak in the natural thermal waterfalls of Saturnia (Cascate del Mulino)
Overnight stay in the picturesque Maremma countryside

We begin our final day driving from southern Tuscany toward the lush hills of the Castelli Romani. Our first stop is the boutique village of Nemi, perched gracefully above a volcanic lake and famous for its wild strawberries and charming local bakeries.
Next, we continue to Castel Gandolfo to enjoy stunning views over Lake Albano, the historic papal summer residence, and a relaxing coffee in the picturesque main piazza. In the afternoon, we make our final elegant drive into the heart of Rome for the luxury car handover and check-in at a fine hotel, bringing an unforgettable driving journey to a close.
Morning visit to the charming lakeside village of Nemi
Views of Lake Albano and coffee in the papal town of Castel Gandolfo
Final elegant drive into the heart of Rome
We begin our final day driving from southern Tuscany toward the lush hills of the Castelli Romani. Our first stop is the boutique village of Nemi, perched gracefully above a volcanic lake and famous for its wild strawberries and charming local bakeries.
Next, we continue to Castel Gandolfo to enjoy stunning views over Lake Albano, the historic papal summer residence, and a relaxing coffee in the picturesque main piazza. In the afternoon, we make our final elegant drive into the heart of Rome for the luxury car handover and check-in at a fine hotel, bringing an unforgettable driving journey to a close.
Morning visit to the charming lakeside village of Nemi
Views of Lake Albano and coffee in the papal town of Castel Gandolfo
Final elegant drive into the heart of Rome
• Experience the thrill of driving the supercar of your choice
• Accommodation in boutique and five-star hotels across Italy (including breakfast)
• A Google Maps file with the complete itinerary, along with recommendations and highlighted hotspots suggested by our professional guides
• Flights
• Tolls
• Fuel
• Meals
• Traffic fines and other reports
• Refundable security deposit up to €3,500 – €6,500 (depending on the car) in case of damages
• Driver’s license, local and international
• Valid credit card with an available credit limit sufficient to cover the required security deposit
• Passports and identification documents
• Recommended: Phone chargers and cables