10-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Florence, Siena, Rome, Arezzo, and Bologna

Day 2 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Today, you'll explore some of the most beautiful places in Milan, including a monument, an art gallery, a castle, a park, a museum and much more! Start your day with a visit to Porta Garibaldi. This worthwhile monument is a must-visit in the city. When you’re ready for your next discovery, continue to Pinacoteca Di Brera, which may be one of the most visually striking places you will experience today.

One of the best things about exploring Milan 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 Sforzesco Castle Art Library, a top-rated castle in the city. If you’re up for more discoveries, don’t forget to reserve some time for Parco Sempione and Museo Della Scienza E Della Tecnologia "leonardo Da Vinci".

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Bring home unique finds from Milan's bustling shopping hub, Galleria Vittorio Emanuele II. Enjoy a leisurely exploration of unique high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Galleria Vittorio Emanuele II offers plenty of options, including primary services, unique landmarks, and community events.

As you explore more of Milan, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

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.

Celebrate another amazing day of your road trip adventure in Italy!

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Milan and Parma. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Savor the day by visiting some of the best places to see in Milan, including an opera house, a shopping mall, a church, a palace and much more! Start your adventure at La Scala. This notable opera house is a must-visit for travelers looking for a unique holiday experience. Make your way to Galleria Vittorio Emanuele Ii located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Duomo Di Milano Museum. Its enchanting features will captivate you. After the church, continue your tour of the city with a visit to Palazzo Della Pilotta. Visitors usually appreciate the visually striking features of this palace.

At the end of the day, you will drive to Florence, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

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 Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and international cuisine in the city.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

Get a good night's sleep and look forward to another great day on the road in Italy!

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Today, you'll explore some of the most beautiful places in Florence, including a public square, a church, a historical landmark, an art gallery, an observation deck and much more! Start your day with a visit to Piazza Della Signoria. This extraordinary public square is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Of Santa Maria Del Fiore, which may be one of the most enchanting places you will experience today.

One of the best things about exploring Florence 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 Ponte Vecchio, a world-famous historical landmark in the city. If you’re up for more discoveries, don’t forget to reserve some time for Uffizi Gallery and Piazzale Michelangelo.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and spend some time relaxing before you head out to tour the city.

Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

Savor another day of unforgettable experiences in Italy!

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 2 nights.

Start at Sistine Chapel, a top-rated chapel in the city.

After exploring the square, visit the wondrous Vatican Museums.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

Say good night to Rome and look forward to another great day of your road trip in Italy!

On day 6 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most widely recognized attractions included on the itinerary is Castel Sant'angelo. This enchanting castle will help you start your sightseeing on top. Then, take a leisurely stroll to Trevi Fountain and learn what makes this romantic monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the timeless Piazza Di Spagna. After exploring the public square, head to Piazza Del Popolo. This impressive public square is a highlight in Rome. As your day continues, stop by Villa Borghese, known for its noteworthy features.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Sant' Eustachio Caffè, known for its inviting atmosphere. Yellowsquare Rome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Portofino provides a great setting to enjoy the night away.

Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!

On day 7 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Rome. In the evening, you’ll end up in Arezzo, where you will stay for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and picturesque spots. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Roman Forum is the first of them. Spend some time admiring this picture-perfect archeological site before continuing your journey. Colosseum is your next stop. This timeless archeological site is one of the best-rated sights in Rome.

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 Altare Della Patria. This culturally significant monument is a sight to behold. To round off your sightseeing experience, visit Pantheon and Piazza Navona.

At the end of the day, you will drive to Arezzo, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Arezzo's best restaurants.

Get ready for an unforgettable culinary journey in Arezzo by reserving a table at Octavin. Renowned as a 1-star Michelin restaurant, it offers an exceptional creative menu. If you're in the mood to try something new, consider La Clandestina, another top spot with a mouthwatering menu.

Keep the excitement of the evening going by visiting a bar or two. Liquid Bar is an excellent place to start.

Relax and recharge in preparation for another adventurous day in Italy!

Dive into day 8 of your remarkable road trip in Italy. Today you will explore Arezzo and La Verna, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna. You’ll stay here for 1 night.

Immerse yourself in Arezzo’s rich culture with today's sightseeing itinerary. Start your journey at San Francesco, Arezzo. This culturally significant church is sure to ignite your curiosity. Next, dive into the respected features of Piazza Grande, a must-visit public square 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 La Verna - Franciscan Sanctuary, a frequently visited monastery.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Bologna, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Experience a symphony of flavors at Ahimè in Bologna by securing a reservation in advance. Renowned for its Bib Gourmand distinction, Ahimè delights its guests with its exceptional variety of meals showcasing delicious country cooking cuisine. For a palate-pleasing alternative, make sure to dine at I Portici, acclaimed for its delectable creative and contemporary specialties. This local 1-star Michelin 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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Al Bricco D'oro, a well-loved spot among locals and tourists. Or, head to Bar Freud E Squisito. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Osteria Del Sole, another top-rated place in the area.

Celebrate another amazing day of your road trip adventure in Italy!

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 1 night.

Bologna is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Bologna Cathedral, an often recommended church that is worthwhile a visit in the city. Nearby, you’ll find Piazza Maggiore, enchanting visitors with its enchanting appeal. Continue your exploration at Two Towers. This monument is one of the city’s most well-known spots.

Enjoy the freedom of exploring Bologna at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Santo Stefano.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Milan. Milan offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely dining experience at Bice Restaurant, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Alto Ristorante, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Nero 9. It’s yet another ideal choice to enhance your time in Milan tonight.

Continue the enjoyment post-dinner at Bhangrabar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Rufus Cocktail Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Ostello Bello Grande. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!