Luxury 11-Day Italy Road Trip from Bologna traveling south to Milan, Pisa, Siena, 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 Milan, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Bologna.

Start your sightseeing with a visit to Two Towers. This tower is rated an average of 4.7 out of 5 stars from 25,975 visitors.

Pinacoteca Nazionale Di Bologna is another popular attraction you could visit today. This art museum has a rating of 4.5 out of 5 stars from 2,400 visitors. Pinacoteca Nazionale Di Bologna attracts up to 15,573 visitors every year.

Piazza Santo Stefano is also highly recommended by travelers. This square has a rating of 4.8 out of 5 stars from 7,617 visitors.

International Museum And Library Of Music is an attraction you won’t want to miss. Around 13,413 people visit this place every year. This music museum is rated an average of 4.5 out of 5 stars in 742 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.

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

Experience a harmony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Known for its 3-star Michelin status, Enrico Bartolini al Mudec offers a delightful variety of dishes highlighting its delicious creative menu. If you're seeking an alternative culinary experience, be sure to explore Seta by Antonio Guida, a highly recommended restaurant known for its enticing international, and contemporary 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 Il Luogo Aimo e Nadia, a highly acclaimed restaurant celebrated for its exceptional italian contemporary, and modern menu.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Nottingham Forest stands out as an excellent choice for a post-dinner cocktail. Alternatively, Armani/bamboo Bar offers an ideal atmosphere to enjoy the pleasures of the night. Mag Cafe is also a great option that provides a perfect setting for a relaxing 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.

Day 3 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 Pinacoteca Di Brera. This art museum is rated an average of 4.7 out of 5 stars by 26,077 visitors. Attracting more than 417 yearly visitors, it’s a top sight you don’t want to miss.

When you’re finished at Pinacoteca Di Brera, head to Sforzesco Castle Art Library. This one-of-a-kind library is rated an average of 4.6 out of 5 stars in 68,714 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Parco Sempione. This park is rated an average of 4.6 out of 5 stars by 72,914 visitors.

If you’re keen to explore more, then consider a visit to Arch Of Peace. This monument is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 27,502 visitors.

To round off your sightseeing experience, make your way to Piazza Gae Aulenti. This famous square is rated an average of 4.6 out of 5 stars by 30,398 travelers.

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

Enjoy a delicious meal at Nero 9, a highly-rated dining destination in Milan. If you're eager to try something different, consider Ristorante la Brisa, another top spot with a tantalizing menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfied customers, it’s an excellent choice to enhance your stay in Milan this evening.

Keep the excitement of the evening going by visiting a bar or two. Kilburn Cocktail Bar Milano is an excellent place to start. You could also check out Bar Frida, offering a different kind of charm. A last recommendation for the day is The Friends Pub Milano. This bar promises an enjoyable experience with tasty drinks and a vibrant 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.

Wake up to day 4 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Milan, and Genoa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Drop by the renowned Galleria Vittorio Emanuele Ii. This popular commercial gallery has been rated an average of 4.7 out of 5 stars by 91,394 visitors.

Another unforgettable place to experience is Duomo Di Milano Museum. Rated 4.8 out of 5 stars by 138,554 visitors, this art museum deserves a spot on today's sightseeing itinerary.

Set your GPS to Genoa and hit the road. Expect a journey of approximately 1 hour 58 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Genoa beckons with new experiences!

Start your sightseeing with a visit to Aquarium Of Genoa. This public aquarium is a popular stop on travelers’ itineraries in Genoa, with an average rating of 4.5 out of 5 stars by 62,259 visitors. Around 1,200,000 people visit this attraction every year.

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.

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

Don’t miss out on dining at Ristorante Capodimonte Pisa, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider Baribaldi Pisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Restaurant -Pizzeria Il Mio Capriccio. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Pisa this evening.

Continue your evening by exploring the vibrant nightlife scene at Jeffer Cocktails & Friends, a prime destination for a thrilling night out. Also, don’t forget to check out Le Parisien Wine Bar, a bar that offers unique local touches. Likewise, Las Volta Cocktailbar provides an excellent alternative for a fun evening.

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

On day 5 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 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.

When you're ready to see some sights, Knights' Square is a great place to start. This square is rated an average of 4.5 out of 5 stars by 9,051 visitors.

Another popular attraction you can visit today is Leaning Tower Of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 travelers. Every year, 3,200,000 travelers come to experience this site to make the most of their time in Pisa.

We also recommend a stop at Pisa Cathedral. The cathedral has been rated an average of 4.8 out of 5 stars by 8,361 visitors.

If you're keen to explore more, consider visiting Piazza Del Duomo, Pisa. This square is a popular attraction with an average rating of 4.7 out of 5 stars from 104,550 reviews.

Campo Santo is another easily accessible place to visit on this day of your trip. Stop by this cemetery, rated 4.6 out of 5 stars in 586 reviews, to discover more of what makes it unique.

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.

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

Enjoy a delicious meal at Antica Trattoria Papei, a highly-rated dining destination in Siena. If you're eager to try something different, consider Osteria Quattro Venti, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfied customers, it’s an excellent choice to enhance your stay in Siena this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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

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 Rome, where you'll be staying for 3 nights. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

Once you're ready to continue your road trip, it's time to buckle up and drive towards Vatican City, eagerly anticipating your arrival in Vatican City. This drive usually takes around 2 hours 40 min, without any stops or traffic disruptions.

Begin your sightseeing with a visit to Sistine Chapel. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Next up, make your way to St. Peter's Basilica. This major basilica has an average rating of 4.8 out of 5 stars from 131,043 reviews. Usually, around 11,000,000 people visit St. Peter's Basilica every year.

When you’re ready for your next sight of the day, continue to Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars by 133,310 visitors. Visiting Vatican Museums means you'll be one of 1,612,530 people who do so every year.

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.

Discover a world of culinary delights in Rome, 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 La Pergola, a 3-star Michelin restaurant offering an incredible mediterranean, and contemporary menu. Alternatively, if your taste buds call for something different, Il Pagliaccio is one of the best restaurants for creative, and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Enoteca La Torre. As a top-rated establishment with 2 Michelin star, it is an ideal choice for mediterranean, and creative cuisine in the city.

Let the evening flow smoothly from dinner to drinks at La Botticella Of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Sant' Eustachio Caffè provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino 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 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 2 nights nights remaining.

A top pick for your self-guided sightseeing tour today is Campo De' Fiori. Previous visitors have rated this square an average of 4.4 out of 5 stars in 51,133 reviews.

Altare Della Patria is a local recommendation that you also can pay a visit today. This architectural structure is rated an average of 4.8 out of 5 stars in 49,843 reviews. The attraction welcomes 1,683,070 visitors every year.

Another attraction you won't want to miss is Roman Forum. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

Colosseum is another outstanding experience in Rome. Around 328,821 travelers have rated this roman amphitheatre an average of 4.7 out of 5 stars. The attraction hosts 7,400,000 visitors annually.

If you long for more, Basilica Di Santa Maria Maggiore is not far away. This major basilica is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.8 out of 5 stars in 27,678 reviews. The attraction gets an estimated 1,683,070 visitors every year.

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.

Savor the flavors at DEROMA - Farine Romane, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider Centro. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

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

Day 8 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.

Seize the day by visiting some of the best attractions in the area, like Piazza Navona. This extraordinary square has an average rating of 4.7 out of 5 stars from 158,771 visitors.

Next, make your way to Pantheon. This roman temple welcomes around 30,000,000 visitors yearly and is rated an average of 4.8 out of 5 stars in 189,682 reviews.

While in Rome, we also recommend a visit to Largo Di Torre Argentina. This square has been rated an average of 4.5 out of 5 stars in 30,433 reviews.

If you’re keen to explore even more, then consider a visit to Circus Maximus. With an average rating of 4.4 out of 5 stars by 44,741 travelers, this circus is a highly recommended stop on your sightseeing around Rome.

Make your way to Castel Sant'angelo, perhaps the most famous museum in Rome. This attraction welcomes around 918,591 visitors annually and is rated an average of 4.7 out of 5 stars in 72,431 reviews.

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

Treat yourself to a delicious dinner at Ristorante Tema, an excellent option for tonight's dining. Looking for something different? Maccheroni offers a tantalizing alternative with its diverse menu. And don’t miss RoYaL Art Cafè Roma. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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 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.

Be one of the day’s first visitors at Trevi Fountain. This sculpture is rated an average of 4.8 out of 5 stars by 343,494 visitors.

When you’re finished at Trevi Fountain, head to Piazza Di Spagna. This one-of-a-kind square is rated an average of 4.7 out of 5 stars in 113,658 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Spanish Steps. This monumental staircase is rated an average of 4.5 out of 5 stars by 57,211 visitors.

If you’re keen to explore more, then consider a visit to Piazza Del Popolo. This square is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 89,807 visitors.

To round off your sightseeing experience, make your way to Villa Borghese. This famous urban zone of rome is rated an average of 4.6 out of 5 stars by 69,749 travelers.

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.

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

Begin your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative, and mediterranean 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 Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary, and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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.

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.

On day 10 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 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.

Take the opportunity to see Piazza Della Signoria. This attraction has an average rating of 4.8 out of 5 stars from 66,956 visitors.

Cathedral Of Santa Maria Del Fiore is another sightseeing hotspot in the area. This church has been rated an average of 4.8 out of 5 stars by 76,359 travelers.

Florence is also the home of Ponte Vecchio. Around 118,099 people have rated this deck arch bridge an average of 4.7 out of 5 stars.

Another place you’ll want to visit is Uffizi Gallery, which hosts up to 2,011,219 visitors every year. With an average rating of 4.7 out of 5 stars from a total of 61,794 reviews, a visit to this national museum is a great idea.

This day of your vacation in Florence is also your chance to admire Piazzale Michelangelo. This must-visit square enjoys an average rating of 4.8 out of 5 stars from 77,744 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.

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

Enjoy an outstanding dining experience at I Portici, a 1-star Michelin restaurant offering an exceptional creative, and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby Bib Gourmand-awardee, Ahimè, known for its delicious country cooking cuisine. Another highly-recommended restaurant in Bologna is Trattoria di Via Serra, a renowned Bib Gourmand restaurant, known for its delicious emilian menu.

Continue your lively evening at Bar Senza Nome, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Maurizio is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Brewdog Bar Bologna 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.