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.

Milan is brimming with adventures. Today’s wonderful stops include a church, a shopping mall, an opera house, a castle, a park and much more! Begin your sightseeing adventure at the iconic Duomo Di Milano Museum and allow yourself time to explore. Just a short distance away you'll find your next stop, Galleria Vittorio Emanuele Ii, a history-steeped shopping mall that draws visitors from far and near.

Continue your journey to La Scala, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the widely recognized Sforzesco Castle Art Library. When you're finished at the castle, Parco Sempione awaits your visit. This park is a majestic highlight on today's itinerary.

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.

Set out on a gastronomic journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of creative cuisine. For a different taste, head over to Seta by Antonio Guida, renowned for its delectable international and contemporary 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 Il Luogo Aimo e Nadia, a highly rated local gem known for its exquisite italian contemporary and modern menu. With a 1-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 Milan.

After enjoying a fulfilling meal, continue your evening at Kilburn Cocktail Bar Milano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Frida offers a welcoming atmosphere for easing into the nightlife. Similarly, The Friends Pub Milano provides an excellent environment for a relaxed and enjoyable evening.

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

On day 3 of your road trip in Italy, you’ll start and end your day in Milan, but spend the day exploring what’s beyond the city. Since you will return to Milan for 1 night more, there’s no need to rush. Experience Milan and Sirmione to the fullest today with this curated day itinerary!

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await! Pinacoteca Di Brera is the perfect place to start. This art gallery is one of the most interesting places to visit in Milan. Next, head to Beach Brema Sirmione, a beloved beach, known for its serene 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 Scaliger Castle. This visually striking castle is a highly recommended experience. Nearby, you'll also find Archaeological Site Of Grotte Di Catullo. Visit these for an interesting touch to your journey.

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.

Enjoy a lovely meal at Bice Restaurant, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Alto Ristorante is another top choice with a popular menu. You could also check for a table at Nero 9. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bhangrabar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Rufus Cocktail Bar offers an ideal atmosphere to enjoy the pleasures of the night. Ostello Bello Grande is also a great option that provides a perfect setting for a relaxing evening.

Savor another day of unforgettable experiences in Italy!

On day 4 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 Verona. In the evening, you’ll end up in Venice, where you will stay for 1 night.

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 awe-inspiring 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.

When you’re done exploring for the day, you’ll drive to your hotel in Venice. 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 Venice. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Discover the culinary delights of Venice by securing a reservation at Local. Esteemed for its 1-star Guide Michelin recognition, this restaurant offers a remarkable selection of contemporary cuisine. For an alternative dining experience, try Wistèria, renowned for its delicious contemporary and venetian dishes. This esteemed 1-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Quadri, a highly recommended local eatery celebrated for its mouthwatering modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Continue the enjoyment post-dinner at Al Parlamento, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, The Caffe Rosso offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Adagio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Venice. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

Immerse yourself in Venice’s rich culture with today's sightseeing itinerary. Start your journey at Rialto Bridge. This history-steeped historical landmark is sure to ignite your curiosity. Next, dive into the history-steeped 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 notable church. For a change of scene, check out Doge's Palace, known for its UNESCO world heritage-listed features. We also recommend visiting Bridge Of Sighs. This monument is a must for anyone looking to experience the city to the fullest.

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

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.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Bologna and Siena, 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 Arezzo. You’ll stay here for 1 night.

Today’s agenda in Bologna includes a monument, a public square, and a church. Two Towers is must-visit monument and a great starting point for the day. Next, continue your journey to Piazza Maggiore, an impressive public square, located just a leisurely stroll away. Next, head to Siena Cathedral, an inviting church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Bologna. When you're ready, let your sightseeing route take you to the astonishing Piazza Del Campo. If you’re looking for more, Tower Of Mangia is also an intriguing attraction that is worthwhile a visit.

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.

Treat yourself to an extraordinary dining experience at Octavin, a 1-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, La Clandestina is another top choice with a popular menu.

After savoring a delicious meal, step into the vibrant nightlife at Liquid Bar, where the evening is just getting started.

Raise your glass and celebrate another amazing day of your road trip 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 - Vatican City. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 4 nights here for some well-deserved relaxation.

Begin your sightseeing with Vatican Museums. This timeless art museum is one of the top attractions in the city. Proceed to Sistine Chapel, another must-visit attraction.

As you wander through the inviting streets of Arezzo, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Saint Peter's Square. This well-known square is a traveler-favorite. Not far away, you’ll find St. Peter's Basilica, another key site on your sightseeing itinerary.

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

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

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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

Day 8 of your road trip across Italy promises a magnificent time exploring Rome. You have 3 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most well-known attractions included on the itinerary is Foro Italico. This photogenic sports complex will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Popolo and learn what makes this romantic public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the astonishing Villa Borghese. After exploring the park, head to Basilica Di Santa Maria Maggiore. This locally renowned church is a highlight in Rome. As your day continues, stop by Archbasilica Of St. John Lateran, known for its culturally significant 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 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.

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.

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

On day 9 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 2 nights and discover all the best things to see and do in the area.

Get ready for a day filled with family-friendly attractions, breathtaking views, and picturesque spots in the charming city of Rome. Your adventure starts at Colosseum, a world-famous local hot spot. Another notable attraction to explore is Roman Forum. This timeless archeological site is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Capitoline Hill. This visually striking public square offers a fascinating experience that many visitors find memorable. Altare Della Patria is also worth visiting, along with Largo Di Torre Argentina. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

Have a fantastic dining experience at Hotel de Russie, a highly recommended choice for tonight's dinner. If you're looking to mix things up, La Taverna Italiana offers an enticing alternative with its varied menu. Additionally, The Parrot Bar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

Raise your glass to another unforgettable day in Italy!

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.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Orange Garden. This romantic park is a highlight of any visit in the city. Then, enjoy Circus Maximus, another picture-perfect attraction that never fails to captivate visitors. Next, head over to Campo De' Fiori, one of the city’s most extraordinary attractions, known for its historic features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Navona. This history-steeped public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Castel Sant'angelo, an impressive castle, 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.

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 wonderful meal at Sofitel Roma Villa Borghese, a top-rated dining spot in Rome. If you're in the mood for something new, try Centro, another premier location with a delectable menu. You might also want to book a table at Ristorante Tema. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Celebrate another amazing day of your road trip adventure 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.

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 world-famous places to visit in Rome. Next, head to Trevi Fountain, a timeless monument, known for its visually striking 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 majestic 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.

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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Start by visiting Basilica Di Santa Maria Novella, Firenze (fi), a prime spot to begin your journey. This history-steeped church is sure to impress. Next on your list is Central Market, another must-visit landmark and well-known food market renowned for its photogenic features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Cathedral Of Santa Maria Del Fiore. This history-steeped church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Galleria Dell'accademia, a locally renowned art gallery.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

Today’s itinerary in Florence covers several incredible sights, including a public square, a historical landmark, an art gallery, a church, an observation deck and much more! Start your adventure at Piazza Della Signoria. This famous public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Ponte Vecchio, a must-see historical landmark 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 Uffizi Gallery. This impressive art gallery offers an enriching experience. For a change of pace, head to Basilica Of Santa Croce In Florence, where you can take in heritage-rich features. Conclude your self-guided sightseeing tour with a visit to Piazzale Michelangelo. 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 Pisa. Pisa 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 Pisa, 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 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.

Let the evening flow smoothly from dinner to drinks at Jeffer Cocktails & Friends, a top-rated bar in the area. For other recommendations, Le Parisien Wine Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Las Volta Cocktailbar offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 14 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Genoa. 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.

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 globally renowned 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 breathtaking 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 intriguing Spiaggia Pubblica Di Priaruggia.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. 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 Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Ristorante la Brisa, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Pasticceria San Carlo, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Continue your evening by exploring the vibrant nightlife scene at Qc Termemilano, a prime destination for a thrilling night out. Also, don’t forget to check out Yguana Cafè, a bar that offers unique local touches.

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