Luxury 10-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Florence, Rome, and Arezzo

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.

Discover a day packed with a charming, an enchanting, a picture-perfect, a heritage-rich, an inviting, a culturally significant, a noteworthy, and a picturesque in Milan. Begin your sightseeing with Duomo Di Milano Museum. This world-famous church is one of the top attractions in the city. Proceed to Galleria Vittorio Emanuele Ii, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Pinacoteca Di Brera. This notable art gallery is a traveler-favorite. Not far away, you’ll find Sforzesco Castle Art Library, another key site on your sightseeing itinerary. Conclude your day at Parco Sempione and uncover why it's recognized as one of the city's most widely recognized attractions.

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 exploring the unique sights of Italy, savor a delicious meal or get refreshed with a drink. We’ve gathered the most recommended restaurants and bars in the city of Milan for you so you can browse their menus in advance and make a reservation.

Experience a taste of local culinary excellence while in Milan by securing a table at Enrico Bartolini al Mudec. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Seta by Antonio Guida, famous for its scrumptious international and contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Luogo Aimo e Nadia, a local favorite celebrated for its exquisite italian contemporary and modern cuisine in Milan. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and modern cuisine lovers seeking top-notch culinary experiences.

Cap off your dinner by heading to Kilburn Cocktail Bar Milano, ideal for a leisurely evening with a drink in hand. Bar Frida is another bar that offers an enjoyable setting. Similarly, The Friends Pub Milano is also a popular place to go on a night out, perfect for relaxing and socializing.

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 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Pisa. 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.

When you’re ready to jump back into the car and say goodbye to Milan, you’ll hit the road in the direction of Pisa. This drive usually takes around 3 hours 17 min. When you arrive, enjoy some sightseeing.

Pisa Cathedral is an often recommended church we recommend making time to visit today. Discover its historic features before continuing your self-guided tour to Piazza Del Duomo, Pisa, an UNESCO world heritage-listed public square that’s well-regarded in the area. Next, stop by Leaning Tower Of Pisa, a historic monument.

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 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 Florence for you, so you can check out the menus and make your reservation in advance.

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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 4 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.

A blend of an instagrammable, a romantic, an awe-inspiring, a heritage-rich, a sacred, a majestic, an UNESCO world heritage-listed, and a masterful await you in Florence on today’s itinerary. First up is the popular food market, Central Market. It's a standout spot that offers a memorable visit. Afterward, continue to Cathedral Of Santa Maria Del Fiore. A visit to this church is an enriching experience for all.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Galleria Dell'accademia. This popular art gallery is an essential stop that should not be missed. Following that, head to David, another must-visit site that will enhance your experience. Lastly, visit Piazzale Michelangelo and learn why this observation deck is renowned as one of the city's most famous attractions.

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.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

Wake up to day 5 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Della Signoria. This symbolic public square is sure to ignite your curiosity. Next, dive into the standout features of Uffizi Gallery, a must-visit art gallery in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Basilica Of Santa Croce In Florence, a popular church.

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.

Experience a symphony of flavors at La Pergola in Rome by securing a reservation in advance. Renowned for its 3-star Michelin distinction, La Pergola delights its guests with its exceptional variety of meals showcasing delicious mediterranean and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Il Pagliaccio, acclaimed for its delectable creative and innovative specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Enoteca La Torre, a top-rated restaurant known for its outstanding menu. Known as a top-rated 2-star Michelin establishment, it's a top choice for mediterranean and creative cuisine in the city.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

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

Day 6 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 2 nights remaining.

Rome is brimming with adventures. Today’s wonderful stops include an archeological site, a monument, a public square, a castle and much more! Begin your sightseeing adventure at the world-famous Colosseum. Just a short distance away is Roman Forum, a picture-perfect archeological site that draws visitors from far and near.

Continue your journey to Pantheon, one of the city’s most world-famous spots that you shouldn’t miss. Another great site to visit is the globally renowned Piazza Navona. Last up on today’s itinerary is a castle. Make your way to Castel Sant'angelo for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of 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.

Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Rome.

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Continue your lively evening at Sant' Eustachio Caffè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yellowsquare Rome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

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.

Day 7 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 adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Altare Della Patria. This noteworthy monument is a highlight of any visit in the city. Then, enjoy Piazza Di Spagna, another enchanting attraction that never fails to captivate visitors. Next, head over to Piazza Del Popolo, one of the city’s most spectacular attractions, known for its symbolic features.

If you’re looking for more, spend time soaking in the atmosphere of Villa Borghese. This noteworthy park is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

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 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 Arezzo, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Vatican 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 11 min. Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Next, make your way to Sistine Chapel, another highlight in the city. Nearby, you will also find Vatican Museums. This world-famous art museum is a top place to see in the area.

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.

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

Prepare for an extraordinary culinary adventure in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant that boasts an exceptional creative menu. If you're eager to try something different, consider La Clandestina, another top spot with a tantalizing menu.

After your meal, keep the night alive at a bar like Liquid Bar, known for its lively atmosphere.

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.

On day 9 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna. The day's journey will conclude in Milan, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await.

Set your GPS to Bologna and hit the road. Expect a journey of approximately 2 hours 5 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Bologna beckons with new experiences!

Make your way to Two Towers, a captivating monument that draws attention for its standout features. Spend some time soaking in the atmosphere before continuing to Piazza Maggiore, a grand public square that stands out in the city. Next, visit Fountain Of Neptune, Bologna, an increasingly popular monument that offers a unique experience. Be sure to also explore Palazzo Re Enzo, a nearby palace, 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 Milan. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Savor the flavors at Bice Restaurant, a top pick for dinner tonight. Alternatively, Alto Ristorante beckons with its unique menu offerings. Also, consider Nero 9. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

Continue your evening by exploring the vibrant nightlife scene at Bhangrabar, a prime destination for a thrilling night out. Also, don’t forget to check out Rufus Cocktail Bar, a bar that offers unique local touches. Likewise, Ostello Bello Grande provides an excellent alternative for a fun evening.

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.