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 will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Milan.

Enjoy all that Porta Garibaldi has to offer. This is an intriguing monument you should not miss. Another must-see is Pinacoteca Di Brera, a notable art gallery in Milan.

When you’re ready for the next sight, head to Sforzesco Castle Art Library. From there, take a leisurely stroll to Parco Sempione, another of the city’s spectacular attractions. We recommend continuing your self-guided tour at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a historic place of interest in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

Indulge in a memorable dining experience at one of Milan's most popular restaurants, and connect with friendly locals for a true cultural experience.

Have a memorable dining experience in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant presenting an exceptional creative menu. For a different culinary experience in Milan, Seta by Antonio Guida shines as one of the top destinations, known for its delicious international and contemporary cuisine. This 2-star Michelin-awardee consistently earns high praises, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Il Luogo Aimo e Nadia is known as a top local spot in Milan for its delicious italian contemporary and modern cuisine. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Kilburn Cocktail Bar Milano, known for its inviting atmosphere. Bar Frida is another great option if you’re looking for a place to get the night started. Similarly, The Friends Pub Milano provides a great setting to enjoy the night away.

Relax and recharge in preparation for another adventurous day 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 places, which are Milan and Parma. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 1 night.

La Scala leaves a lasting impression. This opera house is one of the most popular places to visit in Milan. Next, head to Galleria Vittorio Emanuele Ii, an impressive shopping mall, known for its romantic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Duomo Di Milano Museum. This romantic church is a highly recommended experience. Nearby, you'll also find Palazzo Della Pilotta Visit these for an interesting touch to your journey.

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.

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

Experience a symphony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enoteca Pinchiorri delights its guests with its exceptional variety of meals showcasing delicious italian contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Santa Elisabetta, acclaimed for its delectable creative and mediterranean 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 Gucci Osteria da Massimo Bottura, 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 international cuisine in the city.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Florence. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 1 night.

Piazza Della Signoria makes a great addition to your morning plans. This famous public square is a romantic place to see in Florence. Continue your discovery at Cathedral Of Santa Maria Del Fiore, a symbolic 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 iconic historical landmark offers a symbolic encounter with Florence. Next, make your way to Uffizi Gallery to add another highlight to your day. After that, visit Piazzale Michelangelo, a widely recognized 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.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

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

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

On day 5 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Vatican City are on today's agenda. In the evening, you’ll end up in Rome, where you will stay for 2 nights.

Make a stop at Sistine Chapel. This spectacular chapel is a must-visit for travelers looking for a unique holiday experience. Make your way to St. Peter's Basilica located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Saint Peter's Square. After the square, continue your tour of the city with a visit to Vatican Museums.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and relax 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 Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to an extraordinary dining experience at La Pergola, a 3-star Michelin restaurant offering an incredible mediterranean and contemporary menu. Alternatively, if your taste buds call for something different, Il Pagliaccio is one of the best restaurants for creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Enoteca La Torre. As a top-rated establishment with 2 Michelin star, it is an ideal choice for mediterranean and creative cuisine in the city.

After your meal, keep the night alive at a bar like La Botticella Of Poggi Giovanni, known for its lively atmosphere. Almalu Trastevere is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Viminale Di Pepi Maurilio offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!

Day 6 offers an itinerary packed with the best things to see in Milan. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Awaiting your discovery is the spectacular Castel Sant'angelo, a symbolic castle in Rome. Next, go to Trevi Fountain.

After visiting Castel Sant'angelo and Trevi Fountain, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Piazza Di Spagna. This culturally significant public square offers a unique experience. Piazza Del Popolo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Villa Borghese, one of the most serene places to visit in Rome.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Enjoy a delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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.

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

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

Awaiting your discovery is the world-famous Roman Forum, a breathtaking archeological site in Rome. Next, go to Colosseum.

After visiting Roman Forum and Colosseum, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Altare Della Patria. This culturally significant monument offers a unique experience. Pantheon is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Navona, one of the most history-steeped places to visit in Rome.

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.

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

Experience a taste of local culinary excellence while in Arezzo by securing a table at Octavin. An esteemed 1-star Michelin restaurant, it features an exceptional creative menu. If you're in the mood for something new, try La Clandestina, another premier location with a delectable menu.

Unwind after your meal by stepping into Liquid Bar. This venue is celebrated for its extensive drink selections and cozy vibes.

Relax and look forward to more memorable moments to come!

Your itinerary for day 8 of your road trip in Italy includes 2 stops and features some of the highlights of Arezzo and La Verna. At the end of the day, enjoy the comforts of a top-rated hotel in Bologna, where you'll spend 1 night.

Your adventure in Arezzo is only getting started when you visit San Francesco, Arezzo, an up-and-coming local hot spot. Another notable attraction to explore is Piazza Grande. This locally renowned public square is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Arezzo's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to La Verna - Franciscan Sanctuary. This historic monastery offers a fascinating experience that many visitors find memorable.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Bologna is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Bologna.

Get ready for an unforgettable culinary journey in Bologna by reserving a table at Ahimè. Renowned as a Bib Gourmand restaurant, it offers an exceptional country cooking menu. For a different taste experience, head to I Portici, recognized for its delicious creative and contemporary dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Trattoria di Via Serra, a local favorite known for its delightful emilian cuisine in Bologna. Nestled in the heart of the city, this Bib Gourmand awardee is an ideal choice for emilian foodies seeking culinary excellence.

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise your glass and celebrate another amazing day 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 place, which are Bologna. At the end of the day, you will retreat to the hotel of your choice in Milan, where will spend 1 night.

Check out the worthwhile church, Bologna Cathedral. Afterward, continue to Piazza Maggiore, a public square every traveler should visit. As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Two Towers. This notable monument is an essential stop. Following that, head to Piazza Santo Stefano, another must-visit site that will enhance your experience.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and relax before you head out to tour the city.

Indulge in a memorable dining experience at one of Milan's most popular restaurants, and connect with friendly locals for a true cultural experience.

Have a fantastic dining experience at Bice Restaurant, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Alto Ristorante offers an enticing alternative with its varied menu. Additionally, Nero 9 is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

Keep the evening going at Bhangrabar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Rufus Cocktail Bar, which offers a similarly pleasant setting and great drinks. Another option is Ostello Bello Grande, which provides an inviting environment for unwinding after a busy day out.

Head back to your accommodation in Milan and get some rest to prepare for another magical day of your road trip in Italy.