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

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

Get ready to discover some of the most iconic wonders in Milan, including a church, a shopping mall, an opera house, a castle, a park and much more! Start your day at Duomo Di Milano Museum. This romantic church is a world-famous place to see in Milan. Then, wander over to Galleria Vittorio Emanuele Ii. If noteworthy sites excite you, this shopping mall will be right up your alley. Nearby, you’ll also find La Scala. This romantic opera house is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Sforzesco Castle Art Library is a widely recognized spot in the city that will captivate you with its unique charm. When you’re done at the castle, don’t forget to check out the serene Parco Sempione. Take a moment to appreciate the fascinating details of this widely recognized park.

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 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.

Round off your dining experience by visiting Kilburn Cocktail Bar Milano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Frida, a bar catering to every mood and preference. The Friends Pub Milano likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

At the end of the day, you'll drive back to Milan, where you'll stay for 1 night more.

Savor the day by visiting some of the best places to see in Milan, including an art gallery, a beach, a castle, an archeological site and much more! Start your adventure at Pinacoteca Di Brera. This captivating art gallery is a must-visit for travelers looking for a unique holiday experience. Make your way to Beach Brema Sirmione located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Scaliger Castle. Its visually striking features will captivate you. After the castle, continue your tour of the city with a visit to Archaeological Site Of Grotte Di Catullo. Visitors usually appreciate the history-steeped features of this archeological site.

When you’re done exploring for the day, you’ll return to Milan and your accommodation.

As you explore more of Milan, 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.

Make sure to reserve a table at Bice Restaurant, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Alto Ristorante, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Bhangrabar, where the evening is just getting started. In the same way, Rufus Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Milan. Ostello Bello Grande 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!

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

Milan is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and picturesque spots! Start at Castelvecchio Museum, a well-known museum that is worthwhile a visit in the city. Nearby, you’ll find Castelvecchio Bridge, enchanting visitors with its romantic appeal. Continue your exploration at Verona Arena. This stadium is one of the city’s most globally renowned 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 Piazza Delle Erbe.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Venice. Venice offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you explore more of Venice, 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.

Get ready for an unforgettable culinary journey in Venice by reserving a table at Local. Renowned as a 1-star Michelin restaurant, it offers an exceptional contemporary menu. For a different taste experience, head to Wistèria, recognized for its delicious contemporary and venetian dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Quadri, a local favorite known for its delightful modern cuisine in Venice. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning modern foodies seeking culinary excellence.

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

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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Venice. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Venice. Begin your sightseeing with Rialto Bridge. This wondrous historical landmark is one of the top attractions in the city. Proceed to Piazza San Marco, another must-visit attraction.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to St Mark's Basilica. This well-known church is a traveler-favorite. Not far away, you’ll find Doge's Palace, another key site on your sightseeing itinerary. Bridge Of Sighs is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

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

Enjoy an outstanding dining experience at Ahimè, a Bib Gourmand restaurant offering an exceptional country cooking menu. Alternatively, if you're in the mood for something different, consider the nearby 1-star Michelin-awardee, I Portici, known for its delicious creative and contemporary cuisine. Another highly-recommended place to eat in Bologna is Trattoria di Via Serra, a renowned Bib Gourmand restaurant and a delicious emilian menu.

Continue the enjoyment post-dinner at Bar Al Bricco D'oro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Freud E Squisito offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Osteria Del Sole. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 6 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 Bologna and Siena. In the evening, you’ll end up in Arezzo, where you will stay for 1 night.

Today, you'll explore some of the most beautiful places in Bologna, including a monument, a public square, and a church. Start your day with a visit to Two Towers. This locally renowned monument is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Maggiore, which may be one of the most enchanting places you will experience today.

One of the best things about exploring Bologna 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 Siena Cathedral, a well-known church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Del Campo and Tower Of Mangia.

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

Prepare for an extraordinary culinary adventure in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant that boasts an exceptional creative menu. If you're eager to try something different, consider La Clandestina, another top spot with a tantalizing menu.

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

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

On day 7 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 4 nights.

Begin your adventure at Vatican Museums. This is a world-famous art museum you should not miss. Another must-see is Sistine Chapel, an impressive chapel in Arezzo.

When you’re ready for the next sight, head to Saint Peter's Square. From there, take a leisurely stroll to St. Peter's Basilica, another of the city’s world-famous attractions.

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.

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.

Begin 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.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Almalu Trastevere offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Viminale Di Pepi Maurilio, another top-rated bar in the area.

Raise your glass to another unforgettable day 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 agenda in Rome includes a sport complex, a public square, a park, a church and much more! Foro Italico is must-visit sports complex and a great starting point for the day. Next, continue your journey to Piazza Del Popolo, a spectacular public square, located just a leisurely stroll away. Next, head to Villa Borghese, a mesmerizing park, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the locally renowned Basilica Di Santa Maria Maggiore. If you’re looking for more, Archbasilica Of St. John Lateran is also a locally renowned attraction that is worthwhile a visit.

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.

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 evening by exploring the vibrant nightlife scene at Sant' Eustachio Caffè, a prime destination for a thrilling night out. Also, don’t forget to check out Yellowsquare Rome, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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

Day 9 offers a multitude of experiences. You will stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

Savor the day by visiting some of the best places to see in Rome, including an archeological site, a public square, and a monument. Start your adventure at Colosseum. This globally renowned archeological site is a must-visit for travelers looking for a unique holiday experience. Make your way to Roman Forum located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Capitoline Hill. Its romantic features will captivate you. After the public square, continue your tour of the city with a visit to Altare Della Patria. Visitors usually appreciate the picture-perfect features of this monument. Next up is Largo Di Torre Argentina, a highly recommended archeological site.

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.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

Explore the vibrant nightlife at The Apartment Bar Roma after your meal, a hub for lively evenings and memorable moments. Or, head to Hotel Hassler Roma for a great selection of flavorful drinks and a charming setting.

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

Day 10 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the locally renowned Orange Garden, a visually striking park in Rome. Next, go to Circus Maximus.

After visiting Orange Garden and Circus Maximus, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Campo De' Fiori. This instagrammable public square offers a unique experience. Piazza Navona is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Castel Sant'angelo, one of the most enchanting places to visit in Rome.

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 Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Make sure to reserve a table at Sofitel Roma Villa Borghese, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Centro, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Tema, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Dive into day 11 of your remarkable road trip in Italy. Today you will explore Rome, 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 Florence. You’ll stay here for 2 nights.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Pantheon. This culturally significant monument is a highlight of any visit in the city. Then, enjoy Trevi Fountain, another romantic attraction that never fails to captivate visitors. Next, head over to Piazza Di Spagna, one of the city’s most timeless attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Spanish Steps. This awe-inspiring public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Auditorium Parco Della Musica, a popular concert hall, and take a stroll around the area.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Experience a symphony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enoteca Pinchiorri delights its guests with its exceptional variety of meals showcasing delicious italian contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Santa Elisabetta, acclaimed for its delectable creative and mediterranean specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Gucci Osteria da Massimo Bottura, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and international cuisine in the city.

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.

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

Day 12 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Basilica Di Santa Maria Novella, Firenze (fi). This history-steeped church is a highlight of any visit in the city. Then, enjoy Central Market, another eye-catching attraction that never fails to captivate visitors. Next, head over to Cathedral Of Santa Maria Del Fiore, one of the city’s most extraordinary attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Galleria Dell'accademia. This photogenic art gallery is frequented by locals and tourists alike. To complete your memorable day, make sure to 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.

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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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

Embark on another extraordinary experience on day 13 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Della Signoria. This romantic public square is sure to ignite your curiosity. Next, dive into the awe-inspiring features of Ponte Vecchio, a must-visit historical landmark 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 Uffizi Gallery, an extraordinary art gallery. For a change of scene, check out Basilica Of Santa Croce In Florence, known for its culturally significant features. We also recommend visiting Piazzale Michelangelo. This observation deck is a must for anyone looking to experience the city to the fullest.

At the end of the day, you will drive to Pisa, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Pisa. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Have a fantastic dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a highly recommended choice for tonight's dinner. If you're looking to mix things up, il Mercante offers an enticing alternative with its varied menu. Additionally, La Ghiotteria is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

To truly maximize your evening out, consider visiting Jeffer Cocktails & Friends after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Le Parisien Wine Bar, another bar with an inviting ambiance. Similarly, Las Volta Cocktailbar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Experience an unparalleled adventure on day 14 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Pisa and Genoa. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 1 night here for some well-deserved relaxation.

Today’s itinerary in Pisa covers several incredible sights, including a monument, a public square, a church, a beach and much more! Start your adventure at Leaning Tower Of Pisa. This iconic monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Piazza Del Duomo, Pisa, a must-see public square 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 Pisa Cathedral. This underrated church offers an enriching experience. For a change of pace, head to Spiaggia Pubblica Di Priaruggia, where you can take in eye-catching features. These sights offer a fulfilling end to a perfect day.

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.

As you explore more of Milan, 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.

Treat yourself to a delicious dinner at Ristorante la Brisa, an excellent option for tonight's dining. Looking for something different? Pasticceria San Carlo offers a tantalizing alternative with its diverse menu. And don’t miss UNAHOTELS Cusani Milano. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

After enjoying a fulfilling meal, continue your evening at Qc Termemilano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yguana Cafè offers a welcoming atmosphere for easing into the nightlife.

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