Luxury 9-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Genoa, Florence, 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 remaining.

Today’s route brings a photogenic, a history-steeped, a charming, a gorgeous, a culturally significant, a sacred, and a masterful. The first attraction of today is Royal Palace Of Milan. This locally renowned palace is a historic place to see in Milan. Continue your discovery at Cathedral Square, a visually striking public square with stories to tell.

As you stroll around Milan, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Duomo Di Milano Museum. This wondrous church offers a history-steeped encounter with Milan. Galleria Vittorio Emanuele Ii 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 Milan.

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 Milan.

Dive into a culinary adventure like no other in Milan by booking a table at Enrico Bartolini al Mudec. This popular restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another culinary dining option, venture to Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Il Luogo Aimo e Nadia, a top local restaurant known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

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.

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

Immerse yourself in Milan’s rich culture with today's sightseeing itinerary. Start your journey at Pinacoteca Di Brera. This standout art gallery is sure to ignite your curiosity. Next, dive into the picture-perfect features of Sforzesco Castle Art Library, a must-visit castle 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 Parco Sempione, an astonishing park. For a change of scene, check out Arch Of Peace, known for its picture-perfect features.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Genoa. 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 Genoa so you can check out the menus and make advance reservations.

Experience a harmony of flavors at The Cook in Genoa by securing a reservation in advance. Known for its 1-star Michelin status, The Cook offers a delightful variety of dishes highlighting its delicious modern menu. If you're seeking an alternative culinary experience, be sure to explore San Giorgio, a highly recommended restaurant known for its enticing modern and ligurian cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Il Marin, a highly acclaimed restaurant celebrated for its exceptional seafood and contemporary menu.

Keep the excitement of the evening going by visiting a bar or two. Scurreria Beer & Bagel is an excellent place to start. You could also check out La Lepre, offering a different kind of charm. A last recommendation for the day is Bar Pisacane Iii. 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 4 of your luxury road trip in Italy begins and concludes in the city of Genoa. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Genoa, where you still have 1 night remaining.

Set out on a day brimming with a romantic, a stunning, an instagrammable, a heritage-rich, a culturally significant, and a sacred. Start at the locally renowned Piazza De Ferrari, a visually striking public square in Genoa. Next, go to Genoa Cathedral.

After visiting Piazza De Ferrari and Genoa Cathedral, take time to explore Genoa's streets and absorb its charm. Continue your sightseeing by heading to Aquarium Of Genoa. This picture-perfect aquarium offers a unique experience. Porto Antico is another noteworthy stop.

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 Genoa. Savor the local cuisine and relax as you recount the day's experiences.

Enjoy a delicious meal at Zeffirino, a top-rated dining destination in Genoa. If you're in the mood to try something new, consider Trattoria Vegia Zena, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria delle Grazie. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Genoa this evening.

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

On day 5 of your luxury holiday in Italy, your road trip route will take you exploring the best of Pisa and Cascine Vecchie. 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.

Today's adventure in Pisa promises more breathtaking discoveries and enriching experiences!

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

Your self-guided tour starts at Pisa Cathedral, a beloved church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey. Next, head to Leaning Tower Of Pisa and admire its UNESCO world heritage-listed features. When you’re ready, continue to Piazza Del Duomo, Pisa, a globally renowned public square beloved by locals and tourists alike.

Set your GPS to Cascine Vecchie and hit the road. Expect a journey of approximately 11 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Cascine Vecchie beckons with new experiences!

Make your way to Parco Regionale Migliarino, San Rossore, Massaciuccoli, a locally appreciated nature reserve that draws attention for its romantic features.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile 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 luxury holiday in Italy has plenty more in store for you.

Day 6 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.

Florence is home to plenty of attractions that offer an eye-catching, a historic, a masterful, a romantic, an awe-inspiring, a sacred, a symbolic, and an UNESCO world heritage-listed! Start at Galleria Dell'accademia, a captivating art gallery that is worthwhile a visit in the city. Nearby, you’ll find Cathedral Of Santa Maria Del Fiore, enchanting visitors with its enchanting appeal. Continue your exploration at Central Market. This food market is one of the city’s most interesting spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Basilica Di Santa Maria Novella, Firenze (fi). After exploring the church, head to the iconic Ponte Vecchio. This historical landmark will wrap up today’s self-guided sightseeing tour in the city.

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 Florence, 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 Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await. Piazza Della Signoria is the perfect place to start. This public square is one of the most top-rated places to visit in Florence. Next, head to Uffizi Gallery, a spectacular art gallery, known for its instagrammable features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Basilica Of Santa Croce In Florence. This culturally significant church offers a unique experience that is highly recommended. Meanwhile, Piazzale Michelangelo adds its own distinct charm to your journey.

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.

Set out on a gastronomic journey in Bologna by reserving a table at I Portici. Renowned for its 1-star Michelin recognition, this restaurant presents an outstanding menu of creative and contemporary cuisine. For a different taste, head over to Ahimè, renowned for its delectable country cooking dishes. This distinguished Bib Gourmand-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole 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.

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

Today’s well-planned self-sightseeing route offers several a stunning, a picture-perfect, a historically significant, an inviting, a symbolic, a remarkable, and a charming. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Bologna Cathedral is the first of them. Spend some time admiring this symbolic church before continuing your journey. Fountain Of Neptune, Bologna is your next stop. This often recommended monument is one of the best-rated sights in Bologna.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Maggiore. This visually striking public square is a sight to behold. To round off your sightseeing experience, visit Two Towers and Piazza Santo Stefano.

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.

Treat yourself to a delightful dinner at Bice Restaurant, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Alto Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at Nero 9 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bhangrabar, a well-loved spot among locals and tourists. Or, head to Rufus Cocktail Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ostello Bello Grande, another top-rated place in the area.

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