14-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Venice, Padua, Siena, Rome, Florence, and Pisa

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

Get ready for an exciting day in Milan. Today’s sightseeing agenda includes a park, a castle, an opera house, a shopping mall, a church and much more! Begin your adventure at Parco Sempione. This is a spectacular park you should not miss. Another must-see is Sforzesco Castle Art Library, a widely recognized castle in Milan.

When you’re ready for the next sight, head to La Scala. From there, take a leisurely stroll to Galleria Vittorio Emanuele Ii, another of the city’s impressive attractions. We recommend continuing your self-guided tour at Duomo Di Milano Museum, a history-steeped 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 day of adventure, treat yourself to an exquisite dinner at one of Milan's best restaurants.

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Continue your lively evening at Kilburn Cocktail Bar Milano, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Frida is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, The Friends Pub Milano ensures a night out tailored to your taste.

Celebrate another amazing day of your road trip adventure 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Milan allows for both. Start by heading to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This notable museum provides an insightful glimpse into the city's identity. Next, discover Beach Brema Sirmione, a mesmerizing beach, promising a delightful encounter.

Continue your sightseeing with a visit to Scaliger Castle, a top-rated castle. When you’re done, don’t forget to make a stop at the captivating Archaeological Site Of Grotte Di Catullo.

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

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

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 your meal, keep the night alive at a bar like Bhangrabar, known for its lively atmosphere. Rufus Cocktail Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Ostello Bello Grande offers an excellent atmosphere for those looking to amp up the evening.

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

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

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Castelvecchio Museum. This popular museum is a picture-perfect place to see in Milan. Continue your discovery at Verona Arena, an enchanting stadium with stories to tell.

As you stroll around Milan, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Delle Erbe. This locally renowned public square offers a visually striking encounter with Milan. Next, make your way to Museo Archeologico Al Teatro Romano to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Milan.

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.

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

Dive into a culinary adventure like no other in Venice by booking a table at Local. This popular restaurant holds 1 Michelin star and offers an exceptional menu of contemporary cuisine. For another culinary dining option, venture to Wistèria, celebrated for its delectable contemporary and venetian menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Quadri, a top local restaurant known for its tantalizing modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Let the evening flow smoothly from dinner to drinks at Al Parlamento, a top-rated bar in the area. For other recommendations, The Caffe Rosso provides a perfect setting for rounding out your night with style and great drinks. Likewise, Adagio offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences in Italy!

On day 5 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 Venice. In the evening, you’ll end up in Padua, where you will stay for 1 night.

Savor the day by visiting some of the best places to see in Venice, including a historical landmark, a public square, a church, a palace, a monument and much more! Start your adventure at Rialto Bridge. This wondrous historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza San Marco located in Venice for another exciting encounter.

Next, immerse yourself in the setting of St Mark's Basilica. Its visually striking features will captivate you. After the church, continue your tour of the city with a visit to Doge's Palace. Visitors usually appreciate the history-steeped features of this palace. Next up is Bridge Of Sighs, a highly recommended monument.

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

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

Treat yourself to a delicious dinner at Veganda, an excellent option for tonight's dining. Looking for something different? Osteria Ai Scarponi offers a tantalizing alternative with its diverse menu. And don’t miss Bamboo Cafe (Mma Silvestrin Snc Di Matteo & C). With its reputation for pleasing customers, it’s a fantastic choice for tonight in Padua.

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

Get a good night's sleep and look forward to another great day on the road 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 - Padua and Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Today’s itinerary in Padua covers several incredible sights, including a palace, a church, a monument, a public square and much more! Start your adventure at Ragione Palace. This up-and-coming palace is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of The Basilica Of St. Anthony, a must-see church 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 Two Towers. This interesting monument offers an enriching experience. For a change of pace, head to Piazza Maggiore, where you can take in visually striking features. These sights offer a fulfilling end to a perfect day.

At the end of the day, you will drive to Siena, 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 Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to another unforgettable day 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 3 nights.

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

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

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.

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

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

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

Day 8 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.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Altare Della Patria is the perfect place to start. This monument is one of the most locally renowned places to visit in Rome. Next, head to Trevi Fountain, a globally renowned monument, known for its enchanting 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 symbolic public square is a highly recommended experience. Nearby, you'll also find Spanish Steps and Piazza Del Popolo. Visit these for an interesting touch to your journey.

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.

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.

If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.

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.

Day 9 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.

Get ready to discover some of the most iconic wonders in Rome, including an archeological site, a monument, a public square, a castle and much more! Start your day at Circus Maximus. This culturally significant archeological site is a captivating place to see in Rome. Then, wander over to Largo Di Torre Argentina. If eye-catching sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Pantheon. This culturally significant monument is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Campo De' Fiori is an impressive spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the enchanting Castel Sant'angelo. Take a moment to appreciate the fascinating details of this widely recognized castle.

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.

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 10 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.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and photo-friendly 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. Roman Forum is the first of them. Spend some time admiring this UNESCO world heritage-listed archeological site before continuing your journey. Colosseum is your next stop. This iconic archeological site 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 Piazza Navona. This remarkable public square is a sight to behold. To round off your sightseeing experience, visit Villa Borghese and Auditorium Parco Della Musica.

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

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.

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative and mediterranean cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot for its delicious italian contemporary and international cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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 day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Day 11 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Della Signoria. This history-steeped public square is a highlight of any visit in the city. Then, enjoy Palazzo Vecchio, another romantic attraction that never fails to captivate visitors. Next, head over to Uffizi Gallery, one of the city’s most impressive attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Ponte Vecchio. This visually striking historical landmark is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazzale Michelangelo, an astonishing observation deck, 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.

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.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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

Dive into day 12 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Pisa. You’ll stay here for 1 night.

Florence is home to plenty of attractions that offer fun adventures, picturesque spots, and historic treasures! Start at Basilica Of Santa Croce In Florence, a popular church that is worthwhile a visit in the city. Nearby, you’ll find Cathedral Of Santa Maria Del Fiore, enchanting visitors with its history-steeped appeal. Continue your exploration at Galleria Dell'accademia. This art gallery is one of the city’s most well-known 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 Central Market.

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 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.

Treat yourself to a delightful dinner at Anima di Grano Pizzeria Napoletana Pisa Italy, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try il Mercante? It's another excellent option with a diverse menu. Consider reserving a table at La Ghiotteria as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Jeffer Cocktails & Friends, known for its inviting atmosphere. Le Parisien Wine Bar is another great option if you’re looking for a place to get the night started. Similarly, Las Volta Cocktailbar provides a great setting to enjoy the night away.

Relax and recharge in preparation for another adventurous day 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 Pisa and Genoa. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Get ready for an exciting day in Pisa. Today’s sightseeing agenda includes a monument, a public square, a church, a beach and much more! Begin your adventure at Leaning Tower Of Pisa. This is an iconic monument you should not miss. Another must-see is Piazza Del Duomo, Pisa, a world-famous public square in Pisa.

When you’re ready for the next sight, head to Pisa Cathedral. From there, take a leisurely stroll to Spiaggia Pubblica Di Priaruggia, another of the city’s up-and-coming attractions.

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.

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.

Savor the flavors at Ristorante la Brisa, a top pick for dinner tonight. Alternatively, Pasticceria San Carlo beckons with its unique menu offerings. Also, consider UNAHOTELS Cusani Milano. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

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.

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