10-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Florence, Siena, Rome, Arezzo, and Bologna

Day 2 offers a multitude of experiences. You will stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s itinerary in Milan covers several incredible sights, including a monument, an art gallery, a castle, a park, a museum and much more! Start your adventure at Porta Garibaldi. This increasingly popular monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the eye-catching wonders of Pinacoteca Di Brera, a must-see art gallery 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 Sforzesco Castle Art Library. This impressive castle offers an enriching experience. For a change of pace, head to Parco Sempione, where you can take in eye-catching features. Conclude your self-guided sightseeing tour with a visit to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". These sights offer a fulfilling end to a perfect 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.

Bring home unique finds from Milan's bustling shopping hub, Via della Moscova. Enjoy a leisurely exploration of unique boutiques and stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via della Moscova offers plenty of options, including cafes, primary services, unique landmarks, and community events.

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

Start 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.

Continue your evening by exploring the vibrant nightlife scene at Kilburn Cocktail Bar Milano, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Frida, a bar that offers unique local touches. Likewise, The Friends Pub Milano provides an excellent alternative for a fun evening.

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

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Milan and Parma. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Milan is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and picturesque spots! Start at La Scala, an interesting opera house that is worthwhile a visit in the city. Nearby, you’ll find Galleria Vittorio Emanuele Ii, enchanting visitors with its history-steeped appeal. Continue your exploration at Duomo Di Milano Museum. This church is one of the city’s most iconic spots.

Enjoy the freedom of exploring Milan at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Palazzo Della Pilotta.

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

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Florence, 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 Siena. You’ll stay here for 1 night.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the impressive Piazza Della Signoria, a detailed public square in Florence. Next, go to Cathedral Of Santa Maria Del Fiore.

After visiting Piazza Della Signoria and Cathedral Of Santa Maria Del Fiore, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Ponte Vecchio. This visually striking historical landmark offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazzale Michelangelo, one of the most grand places to visit 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.

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 and reflect on the day's adventures.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 2 nights.

Start your day with a visit to Sistine Chapel. This impressive chapel is a must-visit in the city.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Saint Peter's Square, a locally renowned square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Vatican Museums.

At the end of the day, you will drive to Rome, 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 Rome's best restaurants.

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 delicious meal, get a taste of the vibrant nightlife with a visit to La Botticella Of Poggi Giovanni, known for its inviting atmosphere. Almalu Trastevere is another great option if you’re looking for a place to get the night started. Similarly, Bar Viminale Di Pepi Maurilio provides a great setting to enjoy the night away.

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

On day 6 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most extraordinary attractions included on the itinerary is Castel Sant'angelo. This visually striking castle will help you start your sightseeing on top. Then, take a leisurely stroll to Trevi Fountain and learn what makes this enchanting monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the wondrous Piazza Di Spagna. After exploring the public square, head to Piazza Del Popolo. This top-rated public square is a highlight in Rome. As your day continues, stop by Villa Borghese, known for its mesmerizing features.

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 dinnertime approaches, it's time to head out for a bite to eat in Rome. 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.

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.

Let the evening flow smoothly from dinner to drinks at Sant' Eustachio Caffè, a top-rated bar in the area. For other recommendations, Yellowsquare Rome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day 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 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Arezzo. You will spend 1 night here for some well-deserved relaxation.

Get ready to discover some of the most iconic wonders in Rome, including an archeological site, a monument, and a public square. Start your day at Roman Forum. This culturally significant archeological site is a wondrous place to see in Rome. Then, wander over to Colosseum. If breathtaking sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Altare Della Patria. This historic monument is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pantheon is a world-famous spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the romantic Piazza Navona. Take a moment to appreciate the fascinating details of this world-famous public square.

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

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

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.

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.

On day 8 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 Arezzo and La Verna. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Immerse yourself in Arezzo’s rich culture with today's sightseeing itinerary. Start your journey at San Francesco, Arezzo. This instagrammable church is sure to ignite your curiosity. Next, dive into the romantic features of Piazza Grande, a must-visit public square 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 La Verna - Franciscan Sanctuary, an increasingly popular monastery.

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.

As you explore more of Bologna, 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.

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 dinner by heading to Bar Al Bricco D'oro, ideal for a leisurely evening with a drink in hand. Bar Freud E Squisito is another bar that offers an enjoyable setting. Similarly, Osteria Del Sole is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 1 night.

Today's adventure in Bologna promises more breathtaking discoveries and enriching experiences! Begin at Bologna Cathedral. This picture-perfect church is a highlight of any visit in the city. Then, enjoy Piazza Maggiore, another visually striking attraction that never fails to captivate visitors. Next, head over to Two Towers, one of the city’s most interesting attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Santo Stefano. This visually striking public square is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

At the end of the day, you will drive to Milan, 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 Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at Bice Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, Alto Ristorante boasts a menu that's sure to impress. Also, be sure to check out Nero 9. Known as a local hotspot, it’s a great choice for tonight in Milan.

Explore the vibrant nightlife at Bhangrabar after your meal, a hub for lively evenings and memorable moments. Or, head to Rufus Cocktail Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Ostello Bello Grande is perfect for those looking to extend their night with a touch of local flavor.

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