Luxury One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Bologna, Arezzo, Rome, and Florence

Wake up to day 2 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.

Today’s agenda in Milan includes a church, a shopping mall, an opera house, a castle, a park and much more! Duomo Di Milano Museum is must-visit church and a great starting point for the day. Next, continue your journey to Galleria Vittorio Emanuele Ii, an impressive shopping mall, located just a leisurely stroll away. Next, head to La Scala, an awe-inspiring opera house, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Milan. If you’re looking for more, Sforzesco Castle Art Library is also an extraordinary attraction that is worthwhile a visit. Lastly, don’t miss Parco Sempione, an impressive gem to see 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.

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

Start your culinary exploration in Bologna by securing a reservation at I Portici. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative and contemporary cuisine. For another dining delight, visit Ahimè, celebrated for its delectable country cooking menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

Continue the enjoyment post-dinner at Bar Al Bricco D'oro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Freud E Squisito offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Osteria Del Sole. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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 Bologna and Siena. The day's journey will conclude in Arezzo, 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.

Brace yourself for today’s incredible lineup of attractions in Bologna, featuring a charming, a breathtaking, a visually striking, a standout, and a majestic. Start at Piazza Maggiore, an extraordinary public square in the city. Then, head to Two Towers and soak in the ambiance of this standout monument.

When you’ve had your share of Bologna, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 2 hours 27 min.

Siena Cathedral is an interesting church we recommend making time to visit today. Discover its majestic features before continuing your self-guided tour to Piazza Del Campo, a visually striking public square that’s well-regarded 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.

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.

Continue your evening by exploring the vibrant nightlife scene at Liquid Bar, a prime destination for a thrilling night out.

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 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.

After soaking in Arezzo’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Vatican City, Vatican City. Expect your car journey to take a minimum of 2 hours 32 min. When you arrive in Vatican City, it's time to take a break from the road.

Vatican Museums is a wondrous art museum we recommend making time to visit today.

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.

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

Discover the culinary delights of Rome by securing a reservation at La Pergola. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of mediterranean and contemporary cuisine. For an alternative dining experience, try Il Pagliaccio, renowned for its delicious creative and innovative 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 Enoteca La Torre, a highly recommended local eatery celebrated for its mouthwatering mediterranean and creative menu. With its 2-star Michelin recognition, it offers an unforgettable dining adventure.

Extend your evening after a delightful meal by visiting La Botticella Of Poggi Giovanni, which offers the perfect atmosphere for a night out. Moreover, Almalu Trastevere is another popular option for a drink or two. Likewise, Bar Viminale Di Pepi Maurilio 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.

Day 5 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.

Set out on a day brimming with a romantic, a mesmerizing, an instagrammable, a historic, a grand, an UNESCO world heritage-listed, and a detailed. Start at the famous Spanish Steps, a romantic public square in Rome. Next, go to Piazza Di Spagna.

After visiting Spanish Steps and Piazza Di Spagna, take time to explore Rome's streets and absorb its charm. Continue your sightseeing by heading to Castel Sant'angelo. This visually striking castle offers a unique experience. Roman Forum is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Colosseum, one of the most picture-perfect places to visit in 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.

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

Enjoy a lovely meal at RomAntica, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Coso Ristorante is another top choice with a popular menu. You could also check for a table at DEROMA - Farine Romane. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

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 luxury holiday in Italy has plenty more in store for you.

Wake up to day 6 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.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most timeless attractions included on the itinerary is Pantheon. This culturally significant monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Navona and learn what makes this symbolic public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the top-rated Piazza Del Popolo. After exploring the public square, head to Villa Borghese. This widely recognized park is a highlight in Rome.

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.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Il Palagio, a highly rated local gem known for its exquisite italian contemporary menu. With a 1-star Michelin 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 Florence.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

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

On day 7 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence and Parma. 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.

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 Ponte Vecchio, another enchanting attraction that never fails to captivate visitors. Next, head over to The Boboli Gardens, one of the city’s most well-known attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Piazzale Michelangelo. This history-steeped observation deck is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

Set your GPS to Parma and hit the road. Expect a journey of approximately 2 hours 11 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Parma beckons with new experiences!

Spend your afternoon discovering Piazza Della Pace, an up-and-coming public square known for its standout features.

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 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.

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.

Following your dinner, dive into the local bar culture at Kilburn Cocktail Bar Milano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Frida, the perfect place for those looking to experience the best of the nightlife. Similarly, The Friends Pub Milano provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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