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.

A blend of fun adventures, picturesque spots, and historic treasures await you in Milan on today’s itinerary. First up is the beloved monument, Porta Garibaldi. Afterward, continue to Pinacoteca Di Brera, an art gallery 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 Sforzesco Castle Art Library. This famous castle is an essential stop. Following that, head to Parco Sempione, another must-visit site that will enhance your experience. Don’t forget to stop by Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", an interesting museum in the city.

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.

Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Il Luogo Aimo e Nadia, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and modern cuisine in the city.

Explore the vibrant nightlife at Kilburn Cocktail Bar Milano after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Frida for a great selection of flavorful drinks and a charming setting. Furthermore, The Friends Pub Milano is perfect for those looking to extend their night with a touch of local flavor.

Relax and recharge in preparation for another adventurous day 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.

Set out on a day brimming with fun adventures, romantic experiences, and picturesque spots. Start at the locally renowned La Scala, a historic opera house in Milan. Next, go to Galleria Vittorio Emanuele Ii.

After visiting La Scala and Galleria Vittorio Emanuele Ii, take time to explore Milan's streets and absorb its charm. Continue your sightseeing by heading to Duomo Di Milano Museum. This history-steeped church offers a unique experience. Palazzo Della Pilotta is another noteworthy stop.

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.

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

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 1 night.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Della Signoria. This enchanting public square is sure to ignite your curiosity. Next, dive into the inviting features of Cathedral Of Santa Maria Del Fiore, a must-visit church 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 Ponte Vecchio, a globally renowned historical landmark. For a change of scene, check out Uffizi Gallery, known for its historic features.

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

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.

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.

If you’re not ready to end the night just yet, Meet Life Cafè offers a perfect venue to relax and savor a drink. Similarly, Maudit Pub is well-suited for those looking to unwind in a social setting. Bar Impero Siena is another excellent spot to enjoy a nightcap after a delightful meal.

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 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Vatican City. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 2 nights here for some well-deserved relaxation.

Start your day with a visit to Sistine Chapel. This famous chapel is a must-visit in the city.

One of the best things about exploring Siena 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 Saint Peter's Square, a locally renowned square in the city. If you’re up for more discoveries, don’t forget to reserve some time for 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.

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

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of mediterranean and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative and innovative 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 Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean and creative menu. With a 2-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 Rome.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable 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.

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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Castel Sant'angelo. This spectacular castle provides an insightful glimpse into the city's identity. Next, discover Trevi Fountain, a visually striking monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Di Spagna, a globally renowned public square. When you’re done, don’t forget to make a stop at the famous Piazza Del Popolo. Round off your day at Villa Borghese, another gem in Rome with standout features to discover.

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 enjoying a fulfilling meal, continue your evening at Sant' Eustachio Caffè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yellowsquare Rome offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Portofino provides an excellent environment for a relaxed and enjoyable evening.

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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Rome, 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 Arezzo. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, scenic views, and picturesque spots. Start at Roman Forum, a timeless archeological site in the city. Then, head to Colosseum and soak in the ambiance of this culturally significant archeological site.

There are many interesting places to see in Rome and when you are ready for more, go to Altare Della Patria. This is one of the city’s most notable spots. After exploring the monument, visit the iconic Pantheon. Before wrapping up your self-guided sightseeing tour, head to the wondrous Piazza Navona, a wondrous public square in the city.

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.

As you explore more of Arezzo, 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 harmony of flavors at Octavin in Arezzo by securing a reservation in advance. Known for its 1-star Michelin status, Octavin offers a delightful variety of dishes highlighting its delicious creative menu. If you're looking to mix things up, La Clandestina offers an enticing alternative with its varied menu.

Following your dinner, dive into the local bar culture at Liquid Bar. Enjoy this evening's relaxed ambiance with delightful drinks.

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

On day 8 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 Arezzo and La Verna. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Arezzo is brimming with adventures. Today’s wonderful stops include a church, a public square, and a monastery. Begin your sightseeing adventure at the often recommended San Francesco, Arezzo. Just a short distance away is Piazza Grande, a visually striking public square that draws visitors from far and near.

Continue your journey to La Verna - Franciscan Sanctuary, one of the city’s most beloved spots that you shouldn’t miss.

At the end of the day, you will drive to Bologna, 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 Bologna's most popular restaurants, and connect with friendly locals for an authentic adventure.

Prepare for an extraordinary culinary adventure in Bologna by booking a table at Ahimè, a Bib Gourmand restaurant that boasts an exceptional country cooking menu. For a different flavor experience, head to I Portici, renowned for its delectable creative and contemporary dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Trattoria di Via Serra, a local gem known for its delightful emilian cuisine in Bologna. Nestled in the city's heart, this Bib Gourmand-awardee is a perfect choice for discerning restaurant-goers seeking a new experience.

Round off your dining experience by visiting Bar Al Bricco D'oro, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Freud E Squisito, a bar catering to every mood and preference. Osteria Del Sole likewise offers a unique atmosphere, perfect for a memorable night out.

Head back to your accommodation in Bologna and get some rest in preparation for another magical day of your road trip 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.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Bologna Cathedral. This intriguing church is a historic place to see in Bologna. Continue your discovery at Piazza Maggiore, a culturally significant public square 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 Two Towers. This well-known monument offers a breathtaking encounter with Bologna. Next, make your way to Piazza Santo Stefano to add another highlight to your day. 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.

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.

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.

Savor the flavors at Bice Restaurant, a top pick for dinner tonight. Alternatively, Alto Ristorante beckons with its unique menu offerings. Also, consider Nero 9. With its consistent customer satisfaction, it’s an excellent option for dining 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.

Raise your glass to another unforgettable day in Italy!