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

Wake up to day 2 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 Pisa, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Milan.

Today’s agenda in Milan includes a public square, an opera house, a shopping mall, a church and much more! Cathedral Square is must-visit public square and a great starting point for the day. Next, continue your journey to La Scala, a notable opera house, located just a leisurely stroll away. Next, head to Galleria Vittorio Emanuele Ii, a romantic shopping mall, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Milan. If you’re looking for more, Duomo Di Milano Museum is also an iconic attraction that is worthwhile a visit.

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

Discover a world of culinary delights in Pisa, 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.

Don’t miss out on dining at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

Let the evening flow smoothly from dinner to drinks at Jeffer Cocktails & Friends, a top-rated bar in the area. For other recommendations, Le Parisien Wine Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Las Volta Cocktailbar offers a memorable night with diverse drink options and excellent service.

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

Today’s route brings an awe-inspiring, a photogenic, a standout, a grand, a detailed, an UNESCO world heritage-listed, and a stunning. The first attraction of today is Leaning Tower Of Pisa. This world-famous monument is a breathtaking place to see in Pisa. Continue your discovery at Piazza Del Duomo, Pisa, a stunning public square with stories to tell.

As you stroll around Pisa, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pisa Cathedral. This worthwhile church offers a majestic encounter with Pisa.

Fasten your seatbelt and make your way to your next stop. Lucca, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Pisa to Lucca may take around 31 min without traffic disruptions. Upon arrival in Lucca, we highly recommend checking out some of the top attractions.

Begin your journey at Piazza Dell'anfiteatro and explore the visually striking features.

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

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

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 stress-free luxury holiday in Italy, you will explore the surroundings of Rome. You have 2 nights left in Rome, giving you enough time to explore the region.

Start your day with a visit to Trevi Fountain. This wondrous monument is a must-visit in the city.

As you’ve unraveled the marvels of Rome, it’s time to gear up for the next part of your road trip adventure. Set course for Vatican City! Under favorable conditions, your drive to Vatican City may take around 12 min. Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Vatican Museums is a wondrous art museum we recommend making time to visit today.

When you’re done exploring the best attractions, you’ll drive back to your luxury accommodation near the city of Rome.

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.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Sant' Eustachio Caffè, known for its inviting atmosphere. Yellowsquare Rome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Portofino provides a great setting to enjoy the night away.

Raise your glass and relax after another big day of your luxury holiday in Italy!

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.

Today’s route brings a romantic, a gorgeous, a visually striking, a respected, a symbolic, a masterful, a profound, and an UNESCO world heritage-designated. The first attraction of today is Castel Sant'angelo. This top-rated castle is a culturally significant place to see in Rome. Continue your discovery at Piazza Navona, a romantic public square with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pantheon. This globally renowned monument offers a heritage-rich encounter with Rome. Roman Forum is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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 day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Rome. Savor the local cuisine and relax as you recount the day's experiences.

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

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

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rome. The day's journey will conclude in Florence, 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.

Get ready to discover some of the most iconic wonders in Rome, including a public square and a park. Start your day at Piazza Di Spagna. This history-steeped public square is a wondrous place to see in Rome. Then, wander over to Spanish Steps. If history-steeped sites excite you, this public square will be right up your alley. Nearby, you’ll also find Piazza Del Popolo. This detailed public square is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Villa Borghese is a widely recognized spot in the city that will captivate you with its unique charm.

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.

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 Florence so you can check out the menus and make advance reservations.

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass and relax after another big day of your luxury holiday in Italy!

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.

Get ready to discover some of the most iconic wonders in Florence, including a historical landmark, an art gallery, a public square, a church, an observation deck and much more! Start your day at Ponte Vecchio. This history-steeped historical landmark is a wondrous place to see in Florence. Then, wander over to Uffizi Gallery. If romantic sites excite you, this art gallery will be right up your alley. Nearby, you’ll also find Piazza Della Signoria. This visually striking public square is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Basilica Of Santa Croce In Florence is a notable spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the symbolic Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this spectacular observation deck in Florence.

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 Florence. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

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.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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 8 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 Milan, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence and Verona.

Today’s well-planned self-sightseeing route offers several a charming, a gorgeous, a visually striking, a historic, a stunning, a majestic, and an UNESCO world heritage-designated. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Cathedral Of Santa Maria Del Fiore is the first of them. Spend some time admiring this inviting church before continuing your journey. Central Market is your next stop. This notable food market is one of the best-rated sights in Florence.

Set your GPS to Verona and hit the road. Expect a journey of approximately 2 hours 42 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Verona beckons with new experiences!

Head to Verona Arena, an iconic stadium in Verona. Explore its majestic features at your own pace before you continue your journey.

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 long day of exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Milan for you, so you can check out the menus and make your reservation in advance.

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international and contemporary 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 Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Round off your dining experience by visiting Kilburn Cocktail Bar Milano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Frida, a bar catering to every mood and preference. The Friends Pub Milano likewise offers a unique atmosphere, perfect for a memorable night out.

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.