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

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

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most world-famous attractions included on the itinerary is Duomo Di Milano Museum. This romantic church will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Vittorio Emanuele Ii and learn what makes this remarkable shopping mall unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the notable La Scala. After exploring the opera house, head to Sforzesco Castle Art Library. This top-rated castle is a highlight in Milan. As your day continues, stop by Parco Sempione, 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 you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Milan. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dive into a culinary adventure like no other in Milan by booking a table at Enrico Bartolini al Mudec. This popular restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another culinary dining option, venture to Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Il Luogo Aimo e Nadia, a top local restaurant known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

To truly maximize your evening out, consider visiting Kilburn Cocktail Bar Milano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Frida, another bar with an inviting ambiance. Similarly, The Friends Pub Milano also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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

Milan is brimming with adventures. Today’s wonderful stops include an art gallery, a beach, a castle, an archeological site and much more! Begin your sightseeing adventure at the notable Pinacoteca Di Brera and allow yourself time to explore. Just a short distance away you'll find your next stop, Beach Brema Sirmione, a serene beach that draws visitors from far and near.

Continue your journey to Scaliger Castle, one of the city’s most extraordinary spots that you shouldn’t miss. Another great site to visit is the interesting Archaeological Site Of Grotte Di Catullo.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Milan.

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.

Enjoy a delicious meal 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 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.

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

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

Savor the day by visiting some of the best places to see in Milan, including a museum, a monument, a stadium, a public square and much more! Start your adventure at Castelvecchio Museum. This notable museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Castelvecchio Bridge located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Verona Arena. Its symbolic features will captivate you. After the stadium, continue your tour of the city with a visit to Piazza Delle Erbe. Visitors usually appreciate the history-steeped features of this 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 Venice. Venice 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 Venice. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Experience a taste of local culinary excellence while in Venice by securing a table at Local. An esteemed 1-star Michelin restaurant, it features an exceptional contemporary menu. For an alternative taste experience, visit Wistèria, famous for its scrumptious contemporary and venetian dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Quadri, a local favorite celebrated for its exquisite modern cuisine in Venice. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for modern cuisine lovers seeking top-notch culinary experiences.

Extend your evening after a delightful meal by visiting Al Parlamento, which offers the perfect atmosphere for a night out. Moreover, The Caffe Rosso is another popular option for a drink or two. Likewise, Adagio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Enjoy the perfect balance of relaxation and exploration in Venice today. One of the most iconic attractions included on the itinerary is Rialto Bridge. This culturally significant historical landmark will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza San Marco and learn what makes this enchanting public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the well-known St Mark's Basilica. After exploring the church, head to Doge's Palace. This notable palace is a highlight in Venice. As your day continues, stop by Bridge Of Sighs, known for its culturally significant 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.

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.

Begin your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

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.

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

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a monument, a public square, and a church. Begin your adventure at Two Towers. This is a locally renowned monument you should not miss. Another must-see is Piazza Maggiore, an astonishing public square in Bologna.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Piazza Del Campo, another of the city’s impressive attractions. We recommend continuing your self-guided tour at Tower Of Mangia, a culturally significant place of interest in the city.

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 dinnertime approaches, it's time to head out for a bite to eat in Arezzo. 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 Arezzo by securing a reservation at Octavin. Esteemed for its 1-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. Alternatively, La Clandestina beckons with its unique menu offerings.

Let the evening flow smoothly from dinner to drinks at Liquid Bar, a top-rated bar in the area.

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

When you’re ready, kick off your sightseeing adventure at Vatican Museums. This globally renowned art museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Sistine Chapel, one of the city’s best highlights.

Next, check out Saint Peter's Square, one of the most captivating places to see in Arezzo. This square is a favorite among locals and travelers alike.

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 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.

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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

Relax and recharge in preparation for another adventurous 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 route brings fun adventures, picturesque spots, and historic treasures. The first attraction of today is Foro Italico. This popular sports complex is a heritage-rich place to see in Rome. Continue your discovery at Piazza Del Popolo, a visually striking public square 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 Villa Borghese. This impressive park offers a noteworthy encounter with Rome. Next, make your way to Basilica Di Santa Maria Maggiore to add another highlight to your day. After that, visit Archbasilica Of St. John Lateran, a locally renowned 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 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.

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

Treat yourself to a delicious dinner at RomAntica, an excellent option for tonight's dining. Looking for something different? Coso Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss DEROMA - Farine Romane. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Day 9 of your road trip across Italy promises a magnificent time exploring Rome. You have 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Colosseum. This world-famous archeological site provides an insightful glimpse into the city's identity. Next, discover Roman Forum, a culturally significant archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Capitoline Hill, an interesting public square. When you’re done, don’t forget to make a stop at the notable Altare Della Patria. Round off your day at Largo Di Torre Argentina, another gem in Rome with photogenic features to discover.

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 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.

Following your dinner, dive into the local bar culture at The Apartment Bar Roma. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Hotel Hassler Roma, the perfect place for those looking to experience the best of the nightlife.

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

Day 10 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Today’s itinerary in Rome covers several incredible sights, including a park, an archeological site, a public square, a castle and much more! Start your adventure at Orange Garden. This popular park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Circus Maximus, a must-see archeological site 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 Campo De' Fiori. This famous public square offers an enriching experience. For a change of pace, head to Piazza Navona, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Castel Sant'angelo. 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.

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

Dine in style at Sofitel Roma Villa Borghese, a top recommendation for dinner tonight. Or, for a change of pace, Centro boasts a menu that's sure to impress. Also, be sure to check out Ristorante Tema. Known as a local hotspot, it’s a great choice for tonight in Rome.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 11 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. 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 2 nights.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Pantheon is the perfect place to start. This monument is one of the most wondrous places to visit in Rome. Next, head to Trevi Fountain, a wondrous monument, known for its history-steeped features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Piazza Di Spagna. This visually striking public square is a highly recommended experience. Nearby, you'll also find Spanish Steps and Auditorium Parco Della Musica. Visit these for an interesting touch to your journey.

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.

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

Experience a harmony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Known for its 3-star Michelin status, Enoteca Pinchiorri offers a delightful variety of dishes highlighting its delicious italian contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Santa Elisabetta, a highly recommended restaurant known for its enticing creative and mediterranean cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Gucci Osteria da Massimo Bottura, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and international menu.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

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

Day 12 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Florence is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Basilica Di Santa Maria Novella, Firenze (fi), an interesting church that is worthwhile a visit in the city. Nearby, you’ll find Central Market, enchanting visitors with its visually striking appeal. Continue your exploration at Cathedral Of Santa Maria Del Fiore. This church is one of the city’s most top-rated spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Galleria Dell'accademia.

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 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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

Experience an unparalleled adventure on day 13 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pisa. You will spend 1 night here for some well-deserved relaxation.

Get ready to discover some of the most iconic wonders in Florence, including a public square, a historical landmark, an art gallery, a church, an observation deck and much more! Start your day at Piazza Della Signoria. This visually striking public square is a top-rated place to see in Florence. Then, wander over to Ponte Vecchio. If romantic sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This standout art gallery is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Basilica Of Santa Croce In Florence is a locally renowned spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the romantic Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this top-rated observation deck.

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.

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

Enjoy a lovely dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at il Mercante, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated La Ghiotteria. It’s yet another ideal choice to enhance your time in Pisa tonight.

Keep the excitement of the evening going by visiting a bar or two. Jeffer Cocktails & Friends is an excellent place to start. You could also check out Le Parisien Wine Bar, offering a different kind of charm. A last recommendation for the day is Las Volta Cocktailbar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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.

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.

Pisa is brimming with adventures. Today’s wonderful stops include a monument, a public square, a church, a beach and much more! Begin your sightseeing adventure at the world-famous Leaning Tower Of Pisa and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Del Duomo, Pisa, a stunning public square that draws visitors from far and near.

Continue your journey to Pisa Cathedral, one of the city’s most worthwhile spots that you shouldn’t miss. Another great site to visit is the underrated Spiaggia Pubblica Di Priaruggia.

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.

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.

Treat yourself to a delightful dinner at Ristorante la Brisa, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasticceria San Carlo? It's another excellent option with a diverse menu. Consider reserving a table at UNAHOTELS Cusani Milano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

Following your dinner, dive into the local bar culture at Qc Termemilano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yguana Cafè, the perfect place for those looking to experience the best of the nightlife.

Raise your glass to another unforgettable day in Italy!