Luxury 9-Day Italy Self-Drive Road Trip With Itinerary from Milan to Arezzo, Rome, and Florence

Day 2 of your luxury road trip in Italy begins and concludes in the city of Milan. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Milan, where you still have 1 night remaining.

Savor the day by visiting some of the best places to see in Milan, including a church, a shopping mall, an opera house, a castle, a park and much more! Start your adventure at Duomo Di Milano Museum. This iconic church is a must-visit for travelers looking for a unique holiday experience. Make your way to Galleria Vittorio Emanuele Ii located in Milan for an enchanting atmosphere.

Next, immerse yourself in the setting of La Scala. Its standout features will captivate you. After the opera house, continue your tour of the city with a visit to Sforzesco Castle Art Library. This castle has a picture-perfect appeal. For a change of pace, head to Parco Sempione. As one of the most astonishing attractions in Milan, this park is an excellent place to end your self-guided tour.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

In Milan, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

Wake up to day 3 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Milan and Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start by visiting Pinacoteca Di Brera, a prime spot to begin your journey. This visually striking art gallery is sure to impress.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Bologna. This drive usually takes around 2 hours 32 min, without any stops or traffic disruptions.

Spend your afternoon discovering Two Towers, a popular monument known for its picture-perfect features. After taking in the atmosphere, continue to Piazza Maggiore, a famous public square that is a must-see for anyone visiting the region.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Arezzo. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Discover a world of culinary delights in Arezzo, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Treat yourself to an extraordinary dining experience at Octavin, a 1-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, La Clandestina is another top choice with a popular menu.

Round off your dining experience by visiting Liquid Bar, a prime location for a drink.

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. The day's journey will conclude in Rome, a city that offers you comfort and relaxation for 2 nights. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

When you’re ready to jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of Vatican City, Vatican City. Witness the landscapes transform as you cross the border to Vatican City. This drive usually takes around 2 hours 32 min. When you arrive, enjoy some sightseeing.

Next, visit Sistine Chapel, an astonishing chapel that offers a unique experience. Be sure to also explore St. Peter's Basilica, a nearby major basilica, which is highly recommended by other travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Rome. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Rome so you can check out the menus and make advance reservations.

Experience a taste of local culinary excellence while in Rome by securing a table at La Pergola. An esteemed 3-star Michelin restaurant, it features an exceptional mediterranean and contemporary menu. For an alternative taste experience, visit Il Pagliaccio, famous for its scrumptious creative and innovative dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Enoteca La Torre, a local favorite celebrated for its exquisite mediterranean and creative cuisine in Rome. Located in the heart of the city, this 2-star Michelin restaurant is an ideal pick for mediterranean and creative cuisine lovers seeking top-notch culinary experiences.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise a toast to another amazing day of your luxury holiday in Vatican City, Italy and seize the opportunity to celebrate.

Day 5 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 1 night remaining.

Set out on a day brimming with a romantic, an awe-inspiring, a picture-perfect, a historic, a majestic, a noteworthy, and a stunning. Start at the wondrous Piazza Di Spagna, a respected public square in Rome. Next, go to Trevi Fountain.

After visiting Piazza Di Spagna and Trevi Fountain, take time to explore Rome's streets and absorb its charm. Continue your sightseeing by heading to Pantheon. This culturally significant monument offers a unique experience. Piazza Navona is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Castel Sant'angelo, one of the most romantic places to visit in Rome.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

After a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Rome. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Enjoy a delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Reminisce about your day, look through photos, and prepare for another great day to come! Your luxury holiday in Italy has plenty more in store for you.

Wake up to day 6 of your luxury road trip holiday in Italy! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Florence, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Rome.

A blend of a breathtaking, an instagrammable, a historically significant, a culturally significant, an UNESCO world heritage-listed, a charming, a remarkable, and a serene await you in Rome on today’s itinerary. First up is the iconic archeological site, Roman Forum. It's a standout spot that offers a memorable visit. Afterward, continue to Colosseum. A visit to this archeological site is an enriching experience for all.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Del Popolo. This famous public square is an essential stop that should not be missed. Following that, head to Villa Borghese, another must-visit site that will enhance your experience.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Treat yourself after a day of exploration. Make a reservation at the finest dining and drinking spots in Florence.

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative and mediterranean dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

Reminisce about your day, look through photos, and prepare for another great day to come! Your luxury holiday in Italy has plenty more in store for you.

Day 7 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night remaining.

Start by visiting Piazzale Michelangelo, a prime spot to begin your journey. This visually striking observation deck is sure to impress. Next on your list is Uffizi Gallery, another must-visit landmark and astonishing art gallery renowned for its eye-catching features.

While exploring and sightseeing, take time to savor the ambiance of Florence by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Ponte Vecchio. This majestic historical landmark is a remarkable attraction that offers a unique experience. Piazza Della Signoria also adds charm to your journey, and Cathedral Of Santa Maria Del Fiore wraps up your day with its history-steeped appeal.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

Discover a world of culinary delights in Florence, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

Raise a toast to another amazing day of your luxury holiday in Florence, Italy and seize the opportunity to celebrate.

Wake up to day 8 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Florence and Pisa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Florence is home to plenty of attractions that offer a visually striking and much more! Start at David, an interesting statue that is worthwhile a visit in the city. Nearby, you’ll find Central Market, enchanting visitors with its photogenic appeal.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 1 hour 18 min. When you arrive in Pisa, it's time to take a break from the road.

Savor the rest of your day by heading to Leaning Tower Of Pisa, a world-famous monument that draws visitors from near and far. When you're done, continue on to Piazza Del Duomo, Pisa, where you can soak in the breathtaking surroundings.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Milan. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

After a day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Milan. Savor the local cuisine and relax as you recount the day's experiences.

Make sure to reserve a table at Bice Restaurant, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Alto Ristorante, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Bhangrabar, where the evening is just getting started. In the same way, Rufus Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Milan. Ostello Bello Grande is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Reminisce about your day, look through photos, and prepare for another great day to come! Your stress-free luxury holiday in Italy has plenty more in store for you.