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 what to see in Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Check out 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 impressive 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", a locally renowned museum 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.

For an unforgettable shopping experience, visit Quadrilatero della Moda, the top shopping destination in Milan. Browse local boutique shops and luxury stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Quadrilatero della Moda has to offer, including attractions, essential services, and vibrant community activities.

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

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary 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 Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Unwind after your meal by stepping into Kilburn Cocktail Bar Milano. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Frida offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook The Friends Pub Milano, another top-rated bar in the area.

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

Your itinerary for day 3 of your road trip in Italy includes 2 stops and features some of the highlights of Milan and Parma. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 1 night.

Catch La Scala before the crowds roll in. This instagrammable opera house is sure to ignite your curiosity. Next, dive into the masterful features of Galleria Vittorio Emanuele Ii, a must-visit shopping mall 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 Duomo Di Milano Museum, a world-famous church.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Parma. This drive usually takes around 1 hour 31 min, without any stops or traffic disruptions.

Spend your afternoon discovering Palazzo Della Pilotta, an increasingly popular palace known for its eye-catching features.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence 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 Florence, it's often a good idea to reserve a table in advance.

Start your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative and mediterranean 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 Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Get a good night's sleep and look forward to another great day on the road 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 brings Florence's character to life. This enchanting public square is a highlight of any visit in the city. Then, enjoy Cathedral Of Santa Maria Del Fiore, another visually striking attraction that never fails to captivate visitors. Next, head over to Ponte Vecchio, one of the city’s most iconic attractions, known for its majestic features.

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

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.

Siena 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 Siena.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Vatican City. When you’re not sightseeing, take time to relax at your chosen hotel in Rome, where you’ll be staying for 2 nights.

Vatican City’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 2 hours 40 min. Vatican City welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to Sistine Chapel, a top-rated chapel in Vatican City. This world-famous major basilica is a top recommendation in the area.

When you’re ready to explore more, Saint Peter's Square is an excellent choice. Next, continue your sightseeing at the globally renowned Vatican Museums and discover what makes this art museum unique.

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 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.

If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio is another excellent spot to enjoy a nightcap after a delightful meal.

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 Milan. 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 detailed 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 famous Piazza Del Popolo. Round off your day at Villa Borghese, another gem in Rome with masterful 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.

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.

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.

Continue your lively evening at Sant' Eustachio Caffè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yellowsquare Rome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

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

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Arezzo, where will spend 1 night.

Roman Forum makes a great addition to your morning plans. This world-famous archeological site is a breathtaking place to see in Rome. Continue your discovery at Colosseum, a historic archeological site with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Altare Della Patria. This interesting monument offers an awe-inspiring encounter with Rome. Next, make your way to Pantheon to add another highlight to your day. After that, visit Piazza Navona, a wondrous public square 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 Rome.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Arezzo. Arezzo 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 Arezzo. Enjoy a relaxing evening as you savor delicious local cuisine.

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.

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

Say good night to Arezzo and look forward to another great day of your road trip 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.

Look forward to a unique sightseeing adventure at the curiosity-inducing San Francesco, Arezzo and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Grande, a respected public square that draws visitors from far and near.

When you’ve had your share of Arezzo, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of La Verna. Your travel time is around 1 hour 5 min.

When you're ready for some sights, head to La Verna - Franciscan Sanctuary, an increasingly popular monastery in La Verna. Explore its stunning features at your own pace before you continue your journey.

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.

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.

Dive into a culinary adventure like no other in Bologna by booking a table at Ahimè. This popular restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining option, venture to I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Trattoria di Via Serra, a top local restaurant known for its tantalizing emilian menu. With a Bib Gourmand recognition, it promises an exceptional dining experience not to be missed.

Continue your evening by exploring the vibrant nightlife scene at Bar Al Bricco D'oro, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Freud E Squisito, a bar that offers unique local touches. Likewise, Osteria Del Sole provides an excellent alternative for a fun evening.

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

Your itinerary for day 9 of your road trip in Italy includes 1 stop and features some of the highlights of Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

No visit to Bologna is complete without Bologna Cathedral. This up-and-coming 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 interesting monument is a traveler-favorite. Not far away, you’ll find Piazza Santo Stefano, another key site on your sightseeing itinerary.

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.

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.

Following your dinner, dive into the local bar culture at Bhangrabar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Rufus Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Ostello Bello Grande provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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