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

On day 2 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan 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 Milan today. One of the most frequently visited attractions included on the itinerary is Porta Garibaldi. This heritage-rich monument will help you start your sightseeing on top. Then, take a leisurely stroll to Pinacoteca Di Brera and learn what makes this photogenic art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the astonishing Sforzesco Castle Art Library. After exploring the castle, head to Parco Sempione. This top-rated park is a highlight in Milan. As your day continues, stop by Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", known for its standout 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.

As dinnertime approaches, it's time to head out for a bite to eat in Milan. 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.

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and modern foodies seeking culinary excellence.

After your meal, keep the night alive at a bar like Kilburn Cocktail Bar Milano, known for its lively atmosphere. Bar Frida is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, The Friends Pub Milano offers an excellent atmosphere for those looking to amp up the evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Milan and Parma. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

A blend of family-friendly attractions, romantic experiences, and photo-friendly spots await you in Milan on today’s itinerary. First up is the notable opera house, La Scala. Afterward, continue to Galleria Vittorio Emanuele Ii, a shopping mall every traveler should visit.

As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Duomo Di Milano Museum. This wondrous church is an essential stop. Following that, head to Palazzo Della Pilotta, another must-visit site that will enhance your experience.

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

As you explore more of Florence, 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.

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 Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international 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.

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

On day 4 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 Florence. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Della Signoria. This visually striking public square is a highlight of any visit in the city. Then, enjoy Cathedral Of Santa Maria Del Fiore, another romantic attraction that never fails to captivate visitors. Next, head over to Ponte Vecchio, one of the city’s most world-famous attractions, known for its romantic features.

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

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena 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 Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Vatican City, 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 Rome. You’ll stay here for 2 nights.

Start at Sistine Chapel, a widely recognized chapel that is worthwhile a visit in the city. Continue your exploration at Saint Peter's Square. This square is one of the city’s most captivating spots.

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

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

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

Begin your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

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

Day 6 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Castel Sant'angelo, an extraordinary castle in the city. Then, head to Trevi Fountain and soak in the ambiance of this majestic monument.

There are many interesting places to see in Rome, and when you are ready for more, go to Piazza Di Spagna. This is one of the city’s most iconic grand spots of interest. After exploring the public square, visit the top-rated Piazza Del Popolo. Not far away, you'll also find Villa Borghese. This park is a mesmerizing highlight in Rome.

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

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

Cap off your dinner by heading to Sant' Eustachio Caffè, ideal for a leisurely evening with a drink in hand. Yellowsquare Rome is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Arezzo, which will be your home away from home for 1 night.

Rome is brimming with adventures. Today’s wonderful stops include an archeological site, a monument, and a public square. Begin your sightseeing adventure at the iconic Roman Forum and allow yourself time to explore. Just a short distance away you'll find your next stop, Colosseum, a picture-perfect archeological site that draws visitors from far and near.

Continue your journey to Altare Della Patria, one of the city’s most captivating spots that you shouldn’t miss. Another great site to visit is the globally renowned Pantheon. When you're finished at the monument, Piazza Navona awaits your visit. This public square is a romantic highlight on today's itinerary.

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

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

Enjoy an outstanding dining experience at Octavin, a 1-star Michelin restaurant offering an exceptional creative menu. Alternatively, experience a taste of Arezzo at La Clandestina, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated.

Keep the evening going at Liquid Bar, a great choice for enjoying the after-dinner hours with a drink.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Arezzo and La Verna. When you’re not sightseeing, take time to relax at your selected hotel in Bologna, where you’ll be staying for 1 night.

Brace yourself for today’s incredible lineup of attractions in Arezzo, featuring family-friendly attractions, photo-friendly spots, and historic treasures. Start at San Francesco, Arezzo, an underrated church in the city. Then, head to Piazza Grande and soak in the ambiance of this visually striking public square.

There are many interesting places to see in Arezzo, and when you are ready for more, go to La Verna - Franciscan Sanctuary. This is one of the city’s most beloved historic spots of interest.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna 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 Bologna. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Experience a taste of local culinary excellence while in Bologna by securing a table at Ahimè. An esteemed Bib Gourmand restaurant, it features an exceptional country cooking menu. For an alternative taste experience, visit I Portici, famous for its scrumptious creative and contemporary dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Trattoria di Via Serra, a local favorite celebrated for its exquisite emilian cuisine in Bologna. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for emilian cuisine lovers seeking top-notch culinary experiences.

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

Experience an unparalleled adventure on day 9 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 1 night here for some well-deserved relaxation.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Bologna Cathedral. This frequently visited church provides an insightful glimpse into the city's identity. Next, discover Piazza Maggiore, a majestic public square, promising a delightful encounter.

Continue your sightseeing with a visit to Two Towers, a popular monument. When you’re done, don’t forget to make a stop at the curiosity-inducing Piazza Santo Stefano.

At the end of the day, you will drive to Milan, 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 Milan. 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 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 your delicious meal, get a taste of the vibrant nightlife with a visit to Bhangrabar, known for its inviting atmosphere. Rufus Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, Ostello Bello Grande provides a great setting to enjoy the night away.

Take some time to reflect on your day and savor another beautiful night in Italy.