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.

Let Porta Garibaldi set the tone for the day. Spend some time admiring this symbolic 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 awe-inspiring 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 experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international and contemporary 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 Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

After savoring a delicious meal, step into the vibrant nightlife at Kilburn Cocktail Bar Milano, where the evening is just getting started. In the same way, Bar Frida offers a unique charm perfect for experiencing the local bar scene in Milan. The Friends Pub Milano is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Milan and Parma. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

Experience La Scala, an interesting opera house in the city. Then, head to Galleria Vittorio Emanuele Ii and soak in the ambiance of this enchanting shopping mall.

There are many interesting places to see in Milan, and when you are ready for more, go to Duomo Di Milano Museum. This is one of the city’s most iconic inviting spots of interest. After exploring the church, visit the up-and-coming Palazzo Della Pilotta.

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

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

Enjoy an outstanding dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an exceptional italian contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Santa Elisabetta, known for its delicious creative and mediterranean cuisine. Another highly-recommended place to eat in Florence is Gucci Osteria da Massimo Bottura, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious italian contemporary and international menu.

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Se·sto On Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Il Vinile also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Relax and look forward to more memorable moments to come!

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 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

To truly experience Florence, make sure to drop by Piazza Della Signoria. This top-rated public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Cathedral Of Santa Maria Del Fiore, one of the city’s best highlights.

Next, check out Ponte Vecchio, one of the most timeless places to see in Florence. This historical landmark is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Uffizi Gallery. Wander around and soak in the respected atmosphere this art gallery offers. Then, head to Piazzale Michelangelo, a top-rated observation deck that adds another dimension to your day.

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.

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

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Siena tonight.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to another unforgettable day in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 2 nights.

Sistine Chapel leaves a lasting impression. This chapel is one of the most spectacular places to visit in Siena.

Nearby, you'll also find Vatican Museums. Visit these for an interesting touch to your journey.

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

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.

Continue your evening by exploring the vibrant nightlife scene at La Botticella Of Poggi Giovanni, a prime destination for a thrilling night out. Also, don’t forget to check out Almalu Trastevere, a bar that offers unique local touches. Likewise, Bar Viminale Di Pepi Maurilio provides an excellent alternative for a fun evening.

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

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

Whatever your travel style is, Castel Sant'angelo is an essential stop in Rome. This famous 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, an iconic public square. When you’re done, don’t forget to make a stop at the top-rated Piazza Del Popolo. Round off your day at Villa Borghese, another gem in Rome with mesmerizing features to discover.

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.

Rome 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 Rome.

Enjoy a delicious meal 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.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino 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!

Your itinerary for day 7 of your road trip in Italy includes 1 stop and features some of the highlights of Rome. At the end of the day, enjoy the comforts of a top-rated hotel in Arezzo, where you'll spend 1 night.

Make a stop at Roman Forum. This iconic archeological site is a must-visit for travelers looking for a unique holiday experience. Make your way to Colosseum located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Altare Della Patria. Its culturally significant features will captivate you. After the monument, continue your tour of the city with a visit to Pantheon. Visitors usually appreciate the instagrammable features of this monument. Next up is Piazza Navona, a highly recommended public square.

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

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.

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

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

On day 8 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Arezzo and La Verna are on today's agenda. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Make time for San Francesco, Arezzo, a locally appreciated church that is worthwhile a visit in the city. Nearby, you’ll find Piazza Grande, enchanting visitors with its awe-inspiring appeal. Continue your exploration at La Verna - Franciscan Sanctuary. This monastery is one of the city’s most up-and-coming spots.

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.

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.

Experience a harmony of flavors at Ahimè in Bologna by securing a reservation in advance. Known for its Bib Gourmand status, Ahimè offers a delightful variety of dishes highlighting its delicious country cooking menu. If you're seeking an alternative culinary experience, be sure to explore I Portici, a highly recommended restaurant known for its enticing creative and contemporary cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole is also a great option that provides a perfect setting for a relaxing evening.

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

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Bologna. When you’re not sightseeing, take time to relax at your chosen hotel in Milan, where you’ll be staying for 1 night.

No visit to Bologna is complete without Bologna Cathedral. This frequently visited church is one of the top attractions in the city. Proceed to Piazza Maggiore, another must-visit attraction.

As you wander through the inviting streets of Bologna, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Two Towers. This well-known monument is a traveler-favorite. Not far away, you’ll find Piazza Santo Stefano, another key site on your sightseeing itinerary.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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. If you are looking to dine at a popular restaurant in Milan, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Bice Restaurant, a highly-rated dining destination in Milan. If you're eager to try something different, consider Alto Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

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.

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