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’s well-planned self-sightseeing route offers several family-friendly attractions, picturesque spots, and historic treasures. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Porta Garibaldi is the first of them. Spend some time admiring this standout monument before continuing your journey. Pinacoteca Di Brera is your next stop. This interesting art gallery is one of the best-rated sights in Milan.

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 Sforzesco Castle Art Library. This instagrammable castle is a sight to behold. To round off your sightseeing experience, visit 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.

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

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.

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 3 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 Milan and Parma. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Today’s itinerary in Milan covers several incredible sights, including an opera house, a shopping mall, a church, a palace and much more! Start your adventure at La Scala. This interesting opera house is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the remarkable wonders of Galleria Vittorio Emanuele Ii, a must-see shopping mall in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Duomo Di Milano Museum. This iconic church offers an enriching experience. For a change of pace, head to Palazzo Della Pilotta, where you can take in eye-catching features. These sights offer a fulfilling end to a perfect day.

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.

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.

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.

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Piazza Della Signoria. This famous public square is a romantic place to see in Florence. Continue your discovery at Cathedral Of Santa Maria Del Fiore, a grand church with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Ponte Vecchio. This globally renowned historical landmark offers an enchanting encounter with Florence. Next, make your way to Uffizi Gallery to add another highlight to your day. After that, visit Piazzale Michelangelo, a famous observation deck that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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.

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

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.

Say good night to Siena and look forward to another great 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.

Next, go to St. Peter's Basilica.

Vatican Museums is another noteworthy attraction worthwhile a visit.

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 explore more of Rome, 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.

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.

Let the evening flow smoothly from dinner to drinks at La Botticella Of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Almalu Trastevere provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Viminale Di Pepi Maurilio offers a memorable night with diverse drink options and excellent service.

Celebrate another amazing day of your road trip adventure 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.

Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Castel Sant'angelo. This extraordinary castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Trevi Fountain, one of the city’s best highlights.

Next, check out Piazza Di Spagna, one of the most globally renowned places to see in Rome. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Popolo. Wander around and soak in the enchanting atmosphere this public square offers. Then, head to Villa Borghese, a top-rated park that adds another dimension to your day.

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 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.

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Continue your evening by exploring the vibrant nightlife scene at Sant' Eustachio Caffè, a prime destination for a thrilling night out. Also, don’t forget to check out Yellowsquare Rome, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Arezzo, where you’ll be staying for 1 night.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes an archeological site, a monument, and a public square. Begin your adventure at Roman Forum. This is a world-famous archeological site you should not miss. Another must-see is Colosseum, a timeless archeological site in Rome.

When you’re ready for the next sight, head to Altare Della Patria. From there, take a leisurely stroll to Pantheon, another of the city’s iconic attractions. We recommend continuing your self-guided tour at Piazza Navona, a history-steeped place of interest in the city.

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.

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.

After savoring a delicious meal, step into the vibrant nightlife at Liquid Bar, where the evening is just getting started.

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

Discover a day packed with fun adventures, picturesque spots, and history-rich sites in Arezzo. Begin your sightseeing with San Francesco, Arezzo. This intriguing church is one of the top attractions in the city. Proceed to Piazza Grande, another must-visit attraction.

As you wander through the inviting streets of Arezzo, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to La Verna - Franciscan Sanctuary. This beloved monastery is a traveler-favorite.

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.

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

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.

Keep the evening going at Bar Al Bricco D'oro, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Freud E Squisito, which offers a similarly pleasant setting and great drinks. Another option is Osteria Del Sole, which provides an inviting environment for unwinding after a busy day out.

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

On day 9 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 Bologna. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Today’s agenda in Bologna includes a church, a public square, and a monument. Bologna Cathedral is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Maggiore, a top-rated public square, located just a leisurely stroll away. Next, head to Two Towers, a standout monument, also available for your discovery today.

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

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.

Savor another day of unforgettable experiences in Italy!