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.

No visit to Milan is complete without Porta Garibaldi. This beloved monument is one of the top attractions in the city. Proceed to Pinacoteca Di Brera, another must-visit attraction.

As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Sforzesco Castle Art Library. This spectacular castle is a traveler-favorite. Not far away, you’ll find Parco Sempione, another key site on your sightseeing itinerary. Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

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

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for italian contemporary and modern foodies seeking culinary excellence.

Let the evening flow smoothly from dinner to drinks at Kilburn Cocktail Bar Milano, a top-rated bar in the area. For other recommendations, Bar Frida provides a perfect setting for rounding out your night with style and great drinks. Likewise, The Friends Pub Milano offers a memorable night with diverse drink options and excellent service.

Raise your glass and celebrate another amazing day 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.

To truly experience Milan, make sure to drop by La Scala. This interesting opera house is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Galleria Vittorio Emanuele Ii, one of the city’s best highlights.

Next, check out Duomo Di Milano Museum, one of the most globally renowned places to see in Milan. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Palazzo Della Pilotta. Wander around and soak in the historic atmosphere this palace offers.

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.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

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. Known for great service, it’s a fantastic choice for tonight in Florence.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

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.

One of the most astonishing attractions included on the itinerary is Piazza Della Signoria. This history-steeped public square will help you start your sightseeing on top. Then, take a leisurely stroll to Cathedral Of Santa Maria Del Fiore and learn what makes this enchanting church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the world-famous Ponte Vecchio. After exploring the historical landmark, head to Uffizi Gallery. This top-rated art gallery is a highlight in Florence. As your day continues, stop by Piazzale Michelangelo, known for its majestic 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.

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.

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.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Your itinerary for day 5 of your road trip in Italy includes 1 stop and features some of the highlights of Vatican City. At the end of the day, enjoy the comforts of a top-rated hotel in Rome, where you'll spend 2 nights.

Sistine Chapel is must-visit chapel and a great option for a daytime tour of the area. Continue your journey to St. Peter's Basilica, an iconic major basilica, located just a leisurely stroll away.

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 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.

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Continue the enjoyment post-dinner at La Botticella Of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Almalu Trastevere offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Viminale Di Pepi Maurilio. 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!

Day 6 of your road trip across Italy promises a magnificent time exploring what to see in Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Enjoy all that Castel Sant'angelo has to offer. This is a famous castle you should not miss. Another must-see is Trevi Fountain, a timeless monument in Rome.

When you’re ready for the next sight, head to Piazza Di Spagna. From there, take a leisurely stroll to Piazza Del Popolo, another of the city’s spectacular attractions. We recommend continuing your self-guided tour at Villa Borghese, an eye-catching 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.

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.

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

On day 7 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Rome are on today's agenda. In the evening, you’ll end up in Arezzo, where you will stay for 1 night.

Catch Roman Forum before the crowds roll in. This respected archeological site is sure to ignite your curiosity. Next, dive into the breathtaking features of Colosseum, a must-visit archeological site 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 Altare Della Patria, an interesting monument. For a change of scene, check out Pantheon, known for its heritage-rich features. We also recommend visiting Piazza Navona. This public square is a must for anyone looking to experience the city to the fullest.

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

Have a memorable dining experience in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant presenting an exceptional creative menu. Immerse yourself in the culinary delights of La Clandestina, a popular restaurant in Arezzo. With a menu designed to delight, it ensures a dining experience that transcends the ordinary.

Explore the vibrant nightlife at Liquid Bar after your meal, a hub for lively evenings and memorable moments.

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

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Arezzo and La Verna. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna, where you'll spend 1 night.

Check out the underrated church, San Francesco, Arezzo. Afterward, continue to Piazza Grande, a public square every traveler should visit. As you explore Arezzo’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to La Verna - Franciscan Sanctuary. This worthwhile monastery is an essential stop.

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 symphony of flavors at Ahimè in Bologna by securing a reservation in advance. Renowned for its Bib Gourmand distinction, Ahimè delights its guests with its exceptional variety of meals showcasing delicious country cooking cuisine. For a palate-pleasing alternative, make sure to dine at I Portici, acclaimed for its delectable creative and contemporary specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Trattoria di Via Serra, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for emilian cuisine in the city.

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

Raise your glass and celebrate another amazing day of your road trip 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.

Start your day at Bologna Cathedral. This breathtaking church is a locally appreciated place to see in Bologna. Then, wander over to Piazza Maggiore. If enchanting sites excite you, this public square will be right up your alley. Nearby, you’ll also find Two Towers. This breathtaking monument is a favorite among visitors.

Bologna offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Santo Stefano is a curiosity-inducing spot in the city that will captivate you with its unique charm.

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.

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

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.

After enjoying a fulfilling meal, continue your evening at Bhangrabar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Rufus Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Ostello Bello Grande provides an excellent environment for a relaxed and enjoyable evening.

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