Luxury 7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Bologna, 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 Bologna, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Milan.

Brace yourself for today’s incredible lineup of attractions in Milan, featuring a charming, a gorgeous, a picture-perfect, a historically significant, a noteworthy, a culturally significant, an idyllic, and a sacred. Start at Galleria Vittorio Emanuele Ii, a widely recognized shopping mall in the city. Then, head to Sforzesco Castle Art Library and soak in the ambiance of this stunning castle.

There are many interesting places to see in Milan and when you are ready for more, go to Parco Sempione. This is one of the city’s most impressive spots. After exploring the park, visit the popular Piazza Gae Aulenti. Before wrapping up your self-guided sightseeing tour, head to the timeless Duomo Di Milano Museum, a timeless church in the city.

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

Experience a harmony of flavors at I Portici in Bologna by securing a reservation in advance. Known for its 1-star Michelin status, I Portici offers a delightful variety of dishes highlighting its delicious creative and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Ahimè, a highly recommended restaurant known for its enticing country cooking cuisine. This popular Bib Gourmand-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

After savoring a delicious meal, step into the vibrant nightlife at Bar Al Bricco D'oro, where the evening is just getting started. In the same way, Bar Freud E Squisito offers a unique charm perfect for experiencing the local bar scene in Bologna. Osteria Del Sole 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 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 Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Today’s route brings a charming, a breathtaking, an eye-catching, a respected, a culturally significant, and a sacred. The first attraction of today is Piazza Maggiore. This spectacular public square is a culturally significant place to see in Bologna. Continue your discovery at Two Towers, a breathtaking monument with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Santo Stefano. This worthwhile public square offers an inviting encounter with Bologna. Arco Del Meloncello 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 Bologna.

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.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended restaurant in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition, known for its delicious mediterranean and creative menu.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio 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.

Day 4 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, you'll explore some of the most beautiful places in Rome, including a castle, a monument, a public square, an archeological site and much more! Start your day with a visit to Castel Sant'angelo. This spectacular castle is a must-visit in the city. When you’re ready for your next discovery, continue to Trevi Fountain, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Rome on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Piazza Di Spagna, one of the city’s most iconic public square. If you’re up for more discoveries, don’t forget to reserve some time for Colosseum and Roman Forum.

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

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Sant' Eustachio Caffè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yellowsquare Rome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Portofino is also a great option that provides a perfect setting for a relaxing evening.

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

Get ready for a day filled with a breathtaking, a photogenic, a standout, a grand, a noteworthy, a stunning, and a charming in the charming city of Rome. Your adventure starts at Altare Della Patria, an interesting local hot spot. Another notable attraction to explore is Pantheon. This timeless monument is known for its awe-inspiring appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Navona. This symbolic public square offers a fascinating experience that many visitors find memorable. Piazza Del Popolo is also worth visiting.

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 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.

Start 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.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

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

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Della Signoria. This grand public square is a highlight of any visit in the city. Then, enjoy Piazzale Michelangelo, another enchanting attraction that never fails to captivate visitors.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pisa. This drive usually takes around 1 hour 19 min, without any stops or traffic disruptions.

Spend your afternoon discovering Leaning Tower Of Pisa, a wondrous monument known for its culturally significant features. After taking in the atmosphere, continue to Piazza Del Duomo, Pisa, a wondrous public square that is a must-see for anyone visiting the region.

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.

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.

Let the evening flow smoothly from dinner to drinks at Kilburn Cocktail Bar Milano, a top-rated bar in the area. For other recommendations, Bar Frida provides a perfect setting for rounding out your night with style and great drinks. Likewise, The Friends Pub Milano 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.