Luxury 10-Day Italy Road Trip from Milan to Florence, Siena, Rome, Arezzo, and Bologna

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 nights remaining.

Be one of the day’s first visitors at Porta Garibaldi. This point of interest is rated an average of 4.4 out of 5 stars by 3,436 visitors.

When you’re finished at Porta Garibaldi, head to Pinacoteca Di Brera. This one-of-a-kind art museum is rated an average of 4.7 out of 5 stars in 26,077 reviews. Every year, approximately 417 travelers come here to experience the art museum for themselves.

Beyond the above-mentioned attractions, you also have the opportunity to visit Sforzesco Castle Art Library. This library is rated an average of 4.6 out of 5 stars by 68,714 visitors.

If you’re keen to explore more, then consider a visit to Parco Sempione. This park is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 72,914 visitors.

To round off your sightseeing experience, make your way to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This famous technology museum welcomes around 532,084 visitors annually and is rated an average of 4.5 out of 5 stars by 22,235 travelers.

Discover a world of culinary delights in Milan, 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.

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international, and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary, and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary, and modern foodies seeking culinary excellence.

Unwind after your meal by stepping into Kilburn Cocktail Bar Milano. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Frida offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook The Friends Pub Milano, another top-rated bar in the area.

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.

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 Parma. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

A top pick for your self-guided sightseeing tour today is La Scala. Previous visitors have rated this opera house an average of 4.7 out of 5 stars in 26,219 reviews.

Galleria Vittorio Emanuele Ii is a local recommendation that you also can pay a visit today. This commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

Another attraction you won't want to miss is Duomo Di Milano Museum. This art museum is rated an average of 4.8 out of 5 stars in 138,554 reviews. Every year, around 341,609 travelers visit this site to discover its unique features.

Set your GPS to Parma and hit the road. Expect a journey of approximately 1 hour 31 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Parma beckons with new experiences!

Seize the day by visiting some of the best attractions in the area, like Palazzo Della Pilotta. This extraordinary palace has an average rating of 4.5 out of 5 stars from 5,085 visitors. Each year, around 60,666 people visit this remarkable site to admire its features and learn more about it.

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 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 Florence for you so you can browse their menus in advance and make a reservation.

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative, and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Palagio. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary cuisine in the city.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence. The day's journey will conclude in Siena, 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.

Start your sightseeing with a visit to Piazza Della Signoria. This square is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 66,956 visitors.

Cathedral Of Santa Maria Del Fiore is another popular place of interest you can visit today. The average rating of 4.8 out of 5 stars from 76,359 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Ponte Vecchio. Visitors have rated this deck arch bridge an average of 4.7 out of 5 stars in 118,099 reviews.

Uffizi Gallery, boasting an annual visitor count of up to 2,011,219 people, is another unique site you can experience today. This attraction is a national museum rated an average of 4.7 out of 5 stars in 61,794 reviews.

Make your way to the fantastic Piazzale Michelangelo, perhaps the most famous square in Florence. This attraction is rated 4.8 out of 5 stars by 77,744 travelers.

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

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

Treat yourself to a delicious dinner at Antica Trattoria Papei, an excellent option for tonight's dining. Looking for something different? Osteria Quattro Venti offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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 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 Rome, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Vatican City, Vatican City. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 40 min. Upon reaching Vatican City, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Your sightseeing of the day begins at Sistine Chapel, a remarkable chapel where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Next, satisfy your wanderlust at St. Peter's Basilica. This major basilica has an average rating of 4.8 out of 5 stars from 131,043 travelers. Given the site's popularity, it’s easy to understand why more than 11,000,000 people visit it every year.

Saint Peter's Square is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 38,954 travelers, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Vatican Museums. This well-loved art museum boasts a 4.6 out of 5-star rating from 133,310 reviews. In a single year, approximately 1,612,530 visitors add this sightseeing spot to their travel itineraries.

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

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean, and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative, and innovative cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean, and creative menu.

Following your dinner, dive into the local bar culture at La Botticella Of Poggi Giovanni. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Sant' Eustachio Caffè, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night 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.

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 1 night nights remaining.

Your sightseeing of the day begins at Castel Sant'angelo, a remarkable museum where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 72,431 reviews. Each year, this popular place of interest welcomes approximately 918,591 visitors.

Next, satisfy your wanderlust at Trevi Fountain. This sculpture has an average rating of 4.8 out of 5 stars from 343,494 travelers.

Piazza Di Spagna is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 113,658 travelers, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Piazza Del Popolo. This well-loved square boasts a 4.6 out of 5-star rating from 89,807 reviews.

When there’s still energy left for exploring, Villa Borghese awaits. If you’ve been interested in experiencing an urban zone of rome, this is a top pick rated 4.6 out of 5 stars by 69,749 previous visitors.

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

Treat yourself to a delicious dinner at DEROMA - Farine Romane, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss Centro. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Let the evening flow smoothly from dinner to drinks at The Apartment Bar Roma, a top-rated bar in the area. For other recommendations, Hotel Hassler Roma provides a perfect setting for rounding out your night with style and great drinks.

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

Make Roman Forum one of your first sightseeing stops in Rome. Rated an average of 4.7 out of 5 stars by 114,450 travelers, a visit to this local attraction makes for a great introduction to the area.

Colosseum is a worthwhile attraction you can visit next. This roman amphitheatre is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 328,821 reviews. Up to 7,400,000 travelers visit this site every year to make their time in Rome special.

Today is also the perfect opportunity to drop by Altare Della Patria. This architectural structure has been rated an average of 4.8 out of 5 stars by 49,843 visitors. Up to 1,683,070 people travel to this site annually.

If you’re keen to explore more, head to Pantheon and find out why 30,000,000 people visit this spot every year. A trip to this popular roman temple is also your opportunity to see if it lives up to the reputable 4.8 out of 5-star rating as given by 189,682 previous visitors.

Another top place to visit is Piazza Navona. This square enjoys an average rating of 4.7 out of 5 stars from 158,771 local and international travelers.

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.

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

Begin your culinary exploration in Arezzo by securing a reservation at Octavin. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative cuisine. Or, for a change of pace, La Clandestina boasts a menu that's sure to impress.

After enjoying a fulfilling meal, continue your evening at Liquid Bar, ideal for those looking to unwind with a drink in a comfortable setting.

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 8 of your luxury holiday in Italy, your road trip route will take you exploring the best of Arezzo, and La Verna. The day's journey will conclude in Bologna, 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.

Kick off the day at San Francesco, Arezzo, a top pick for today’s sightseeing. Attracting approximately 20,939 visits every year, this attraction is a must-see. This minor basilica is rated an average of 4.6 out of 5 stars in 2,377 reviews.

Today is also your chance to visit Piazza Grande. Piazza Grande is a square with an average rating of 4.6 out of 5 stars from 14,465 reviews.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in La Verna. This drive usually takes around 1 hour 5 min, without any stops or traffic disruptions.

Begin your sightseeing with a visit to La Verna - Franciscan Sanctuary. This church is rated an average of 4.8 out of 5 stars in 7,374 reviews.

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

Discover a world of culinary delights in Bologna, 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.

Experience a symphony of flavors at I Portici in Bologna by securing a reservation in advance. Renowned for its 1-star Michelin distinction, I Portici delights its guests with its exceptional variety of meals showcasing delicious creative, and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Ahimè, acclaimed for its delectable country cooking specialties. This local Bib Gourmand establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Trattoria di Via Serra, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for emilian cuisine in the city.

To truly maximize your evening out, consider visiting Bar Freud E Squisito after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Osteria Del Sole, another bar with an inviting ambiance. Similarly, Macondo - Cocktail Bar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 9 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 Bologna.

When you're ready to see some sights, Bologna Cathedral is a great place to start. This catholic cathedral is rated an average of 4.6 out of 5 stars by 3,852 visitors.

Another popular attraction you can visit today is Piazza Maggiore. This square has an average rating of 4.7 out of 5 stars from 64,523 travelers.

We also recommend a stop at Two Towers. The tower has been rated an average of 4.7 out of 5 stars by 25,975 visitors.

If you're keen to explore more, consider visiting Piazza Santo Stefano. This square is a popular attraction with an average rating of 4.8 out of 5 stars from 7,617 reviews.

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.

Enjoy a delicious meal at Vento di Sardegna, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Palazzo Parigi Hotel & Grand Spa Milano, another top spot with a mouthwatering menu. You might also want to secure a reservation at Galleria Restaurant. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Milan this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bhangrabar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Rufus Cocktail Bar offers an ideal atmosphere to enjoy the pleasures of the night. Ostello Bello Grande is also a great option that provides a perfect setting for a relaxing evening.

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