Two-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Verona, Venice, Bologna, Arezzo, Rome, Florence, and Pisa

Day 2 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Today's adventure in Milan promises more breathtaking discoveries and enriching experiences! Begin at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This history-steeped museum is a highlight of any visit in the city. Then, enjoy Santa Maria Delle Grazie Church, another instagrammable attraction that never fails to captivate visitors. Next, head over to Sforzesco Castle Art Library, one of the city’s most spectacular attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Parco Sempione. This awe-inspiring park is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Arch Of Peace, a notable monument, and take a stroll around the area.

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.

Experience shopping bliss at Milan as you explore Via della Moscova. Take a leisurely stroll through unique boutiques and shops, where local treasures are waiting to be found. Beyond shopping, Via della Moscova offers more options, including cafes, unique attractions, key services, and vibrant events.

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

Experience a taste of local culinary excellence while in Milan by securing a table at Enrico Bartolini al Mudec. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Seta by Antonio Guida, famous for its scrumptious international and contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Luogo Aimo e Nadia, a local favorite celebrated for its exquisite italian contemporary and modern cuisine in Milan. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and modern cuisine lovers seeking top-notch culinary experiences.

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.

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

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

A blend of fun adventures, romantic experiences, and scenic views await you in Milan on today’s itinerary. First up is the iconic church, Duomo Di Milano Museum. Afterward, continue to Galleria Vittorio Emanuele Ii, a shopping mall 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 La Scala. This popular opera house is an essential stop. Following that, head to Pinacoteca Di Brera, another must-visit site that will enhance your experience. Don’t forget to stop by Scaliger Castle, an astonishing castle in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Verona. Check in and spend some time relaxing before you head out to tour the city.

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

Discover the culinary delights of Verona by securing a reservation at Osteria Mondo d'Oro. Esteemed for its a Bib Gourmand award, this restaurant offers a remarkable selection of italian and seasonal cuisine. For an alternative dining experience, try Casa Perbellini 12 Apostoli, renowned for its delicious creative 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 Desco, a highly recommended local eatery celebrated for its mouthwatering italian contemporary menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

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

Raise your glass to another unforgettable day in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Venice, 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 Bologna. You’ll stay here for 1 night.

Immerse yourself in Venice’s rich culture with today's sightseeing itinerary. Start your journey at Rialto Bridge. This romantic historical landmark is sure to ignite your curiosity. Next, dive into the romantic features of Piazza San Marco, 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 St Mark's Basilica, a locally renowned church. For a change of scene, check out Doge's Palace, known for its visually striking features.

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

Prepare for an extraordinary culinary adventure in Bologna by booking a table at Ahimè, a Bib Gourmand restaurant that boasts an exceptional country cooking menu. For a different flavor experience, head to I Portici, renowned for its delectable creative and contemporary dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Trattoria di Via Serra, a local gem known for its delightful emilian cuisine in Bologna. Nestled in the city's heart, this Bib Gourmand-awardee is a perfect choice for discerning restaurant-goers seeking a new experience.

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.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Bologna and Siena. 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.

Savor the day by visiting some of the best places to see in Bologna, including a public square, a monument, and a church. Start your adventure at Piazza Maggiore. This extraordinary public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Two Towers located in Bologna for an enchanting atmosphere.

Next, immerse yourself in the setting of Siena Cathedral. Its visually striking features will captivate you. After the church, continue your tour of the city with a visit to Piazza Del Campo. This public square has a romantic appeal.

When you’re done exploring for the day, you’ll drive to your hotel in Arezzo. 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 Arezzo. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day'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.

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

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Vatican City. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 4 nights.

Enjoy the perfect balance of relaxation and exploration in Arezzo today. One of the most timeless attractions included on the itinerary is Vatican Museums.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the astonishing Sistine Chapel. After exploring the chapel, head to St. Peter's Basilica. This wondrous major basilica is a highlight in Arezzo.

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

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.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended place to eat in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition and a delicious mediterranean and creative menu.

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.

Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!

On day 8 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 3 nights and discover all the best things to see and do in the area.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and picturesque spots. 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. Altare Della Patria is the first of them. Spend some time admiring this culturally significant monument before continuing your journey. Archbasilica Of St. John Lateran is your next stop. This well-known church is one of the best-rated sights in Rome.

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 Capitoline Hill. This enchanting public square is a sight to behold. To round off your sightseeing experience, visit Roman Forum and Colosseum.

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 you explore more of Rome, 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.

Don’t miss out on dining 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.

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.

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

Day 9 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

A blend of fun adventures, photo-friendly spots, and history-rich sites await you in Rome on today’s itinerary. First up is the interesting church, Basilica Di Santa Maria Maggiore. Afterward, continue to Orange Garden, a park every traveler should visit.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Circus Maximus. This locally renowned archeological site is an essential stop. Following that, head to Castel Sant'angelo, another must-visit site that will enhance your experience.

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.

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

Enjoy a delicious meal at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Keep the excitement of the evening going by visiting a bar or two. The Apartment Bar Roma is an excellent place to start. You could also check out Hotel Hassler Roma, offering a different kind of charm.

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

Day 10 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a park, a public square, and a monument. Begin your adventure at Villa Borghese. This is a top-rated park you should not miss. Another must-see is Piazza Del Popolo, a spectacular public square in Rome.

When you’re ready for the next sight, head to Spanish Steps. From there, take a leisurely stroll to Piazza Di Spagna, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Trevi Fountain, a visually striking place of interest in the city.

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.

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 a delightful dinner at Sofitel Roma Villa Borghese, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Centro? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Tema as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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

On day 11 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Start by visiting Largo Di Torre Argentina, a prime spot to begin your journey. This heritage-rich archeological site is sure to impress. Next on your list is Pantheon, another must-visit landmark and iconic monument renowned for its instagrammable features.

While exploring and sightseeing, take time to savor the ambiance of Rome by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Piazza Navona. This enchanting public square is a remarkable attraction that offers a unique experience. Campo De' Fiori also adds charm to your journey, and Foro Italico wraps up your day with its heritage-rich appeal.

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.

As you explore more of Florence, 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.

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 Il Palagio, a top local spot known for its tantalizing italian contemporary menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

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

Day 12 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Piazzale Michelangelo. This impressive observation deck is a visually striking place to see in Florence. Continue your discovery at Uffizi Gallery, a romantic art gallery 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 globally renowned historical landmark offers an enchanting encounter with Florence. Next, make your way to Piazza Della Signoria to add another highlight to your day. After that, visit Basilica Of Santa Croce In Florence, a popular church 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.

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 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 and reflect on the day's adventures.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences in Italy!

On day 13 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 Florence. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the famous Cathedral Of Santa Maria Del Fiore, a romantic church in Florence. Next, go to Galleria Dell'accademia.

After visiting Cathedral Of Santa Maria Del Fiore and Galleria Dell'accademia, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Central Market. This instagrammable food market offers a unique experience. Basilica Di Santa Maria Novella, Firenze (fi) is another noteworthy stop.

When you’re done exploring for the day, you’ll drive to your hotel in Pisa. Check in and spend some time relaxing before you head out to tour the city.

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

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Mercante, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue the enjoyment post-dinner at Jeffer Cocktails & Friends, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Le Parisien Wine Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Las Volta Cocktailbar. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Dive into day 14 of your remarkable road trip in Italy. Today you will explore Pisa and Genoa, 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 Milan. You’ll stay here for 1 night.

Get ready for an exciting day in Pisa. Today’s sightseeing agenda includes a public square, a monument, a cemetery, a beach and much more! Begin your adventure at Knights' Square. This is an underrated public square you should not miss. Another must-see is Leaning Tower Of Pisa, a wondrous monument in Pisa.

When you’re ready for the next sight, head to Piazza Del Duomo, Pisa. From there, take a leisurely stroll to Campo Santo, another of the city’s often recommended attractions. We recommend continuing your self-guided tour at Spiaggia Pubblica Di Priaruggia, a mesmerizing place of interest in the city.

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

Don’t miss out on dining at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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.

Say good night to Milan and look forward to another great day of your road trip in Italy!