14-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Venice, Padua, Siena, 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.

Today, you'll explore some of the most beautiful places in Milan, including a park, a castle, an opera house, a shopping mall, a church and much more! Start your day with a visit to Parco Sempione. This impressive park is a must-visit in the city. When you’re ready for your next discovery, continue to Sforzesco Castle Art Library, which may be one of the most historic places you will experience today.

One of the best things about exploring Milan 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 La Scala, an interesting opera house in the city. If you’re up for more discoveries, don’t forget to reserve some time for Galleria Vittorio Emanuele Ii and Duomo Di Milano Museum.

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 Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Kilburn Cocktail Bar Milano, known for its inviting atmosphere. Bar Frida is another great option if you’re looking for a place to get the night started. Similarly, The Friends Pub Milano provides a great setting to enjoy the night away.

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

On day 3 of your road trip, you’ll start and end your day in Milan, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Milan and Sirmione. You still have 1 night left in Milan.

Get ready for a day filled with family-friendly attractions, photo-friendly spots, and history-rich sites in the charming city of Milan. Your adventure starts at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a well-known local hot spot. Another notable attraction to explore is Beach Brema Sirmione. This intriguing beach is known for its photogenic appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Scaliger Castle. This romantic castle offers a fascinating experience that many visitors find memorable. Archaeological Site Of Grotte Di Catullo is also worth visiting.

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

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

Enjoy a lovely dining experience at Bice Restaurant, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Alto Ristorante, 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 Nero 9. It’s yet another ideal choice to enhance your time in Milan tonight.

Continue your evening by exploring the vibrant nightlife scene at Bhangrabar, a prime destination for a thrilling night out. Also, don’t forget to check out Rufus Cocktail Bar, a bar that offers unique local touches. Likewise, Ostello Bello Grande provides an excellent alternative for a fun evening.

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

Prepare for a day full of family-friendly attractions, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Castelvecchio Museum. This interesting museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Verona Arena, one of the city’s best highlights.

Next, check out Piazza Delle Erbe, one of the most interesting places to see in Milan. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Museo Archeologico Al Teatro Romano. Wander around and soak in the awe-inspiring atmosphere this museum offers.

At the end of the day, you will drive to Venice, 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 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.

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.

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

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 Padua. You will spend 1 night here for some well-deserved relaxation.

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 grand historical landmark will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza San Marco 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 captivating St Mark's Basilica. After exploring the church, head to Doge's Palace. This locally renowned palace is a highlight in Venice. Lastly, don’t forget to check out the notable Bridge Of Sighs. Enjoy exploring this incredible monument at your own pace.

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.

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

Enjoy a delicious meal at Veganda, a highly-rated dining destination in Padua. If you're eager to try something different, consider Osteria Ai Scarponi, another top spot with a tantalizing menu. You might also want to secure a reservation at Bamboo Cafe (Mma Silvestrin Snc Di Matteo & C). With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Padua this evening.

Cap off your dinner by heading to Il Gottino - Wine Bar, ideal for a leisurely evening with a drink in hand. Brutal is another bar that offers an enjoyable setting. Similarly, Al Buscaglione is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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

Start by visiting Ragione Palace, a prime spot to begin your journey. This standout palace is sure to impress. Next on your list is The Basilica Of St. Anthony, another must-visit landmark and popular church renowned for its heritage-rich features.

While exploring and sightseeing, take time to savor the ambiance of Padua by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Two Towers. This historic monument is a remarkable attraction that offers a unique experience. Piazza Maggiore also adds charm to your journey.

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

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

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

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.

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

On day 7 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 Vatican City. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

First up is the spectacular chapel, Sistine Chapel. Afterward, continue to St. Peter's Basilica, a major basilica every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Saint Peter's Square. This locally renowned square is an essential stop. Following that, head to Vatican Museums, another must-visit site that will enhance your experience.

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

Dive into a culinary adventure like no other in Rome by booking a table at La Pergola. This popular restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another culinary dining option, venture to Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Enoteca La Torre, a top local restaurant known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Extend your evening after a delightful meal by visiting La Botticella Of Poggi Giovanni, which offers the perfect atmosphere for a night out. Moreover, Almalu Trastevere is another popular option for a drink or two. Likewise, Bar Viminale Di Pepi Maurilio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Get ready to discover some of the most iconic wonders in Rome, including a monument and a public square. Start your day at Altare Della Patria. This historic monument is a locally renowned place to see in Rome. Then, wander over to Trevi Fountain. If history-steeped sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Di Spagna. This romantic public square 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, Spanish Steps 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 symbolic Piazza Del Popolo. Take a moment to appreciate the fascinating details of this top-rated public square 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 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.

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.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

On day 9 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, scenic views, and picturesque spots. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Circus Maximus is the first of them. Spend some time admiring this picture-perfect archeological site before continuing your journey. Largo Di Torre Argentina is your next stop. This captivating 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 Pantheon. This photogenic monument is a sight to behold. To round off your sightseeing experience, visit Campo De' Fiori and Castel Sant'angelo.

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 delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

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

On day 10 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.

Savor the day by visiting some of the best places to see in Rome, including an archeological site, a public square, a park, a concert hall and much more! Start your adventure at Roman Forum. This wondrous archeological site is a must-visit for travelers looking for a unique holiday experience. Make your way to Colosseum located in Rome for an enchanting atmosphere.

Next, immerse yourself in the setting of Piazza Navona. Its history-steeped features will captivate you. After the public square, continue your tour of the city with a visit to Villa Borghese. This park has a serene appeal. For a change of pace, head to Auditorium Parco Della Musica. As one of the most popular attractions in Rome, this concert hall is an excellent place to end your self-guided tour.

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.

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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await. Piazza Della Signoria is the perfect place to start. This public square is one of the most spectacular places to visit in Florence. Next, head to Palazzo Vecchio, an interesting palace, known for its awe-inspiring 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 Uffizi Gallery. This romantic art gallery offers a unique experience that is highly recommended. Meanwhile, Ponte Vecchio adds its own distinct charm to your journey. Finish your day with a visit to Piazzale Michelangelo, a romantic observation deck in Florence.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Enjoy a delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Embark on another extraordinary experience on day 12 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.

Today, you'll explore some of the most beautiful places in Florence, including a church, an art gallery, and a food market. Start your day with a visit to Basilica Of Santa Croce In Florence. This notable church is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Of Santa Maria Del Fiore, which may be one of the most symbolic places you will experience today.

One of the best things about exploring Florence 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 Galleria Dell'accademia, a popular art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Central Market.

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.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Pisa. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delicious dinner at Anima di Grano Pizzeria Napoletana Pisa Italy, an excellent option for tonight's dining. Looking for something different? il Mercante offers a tantalizing alternative with its diverse menu. And don’t miss La Ghiotteria. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Pisa.

Explore the vibrant nightlife at Jeffer Cocktails & Friends after your meal, a hub for lively evenings and memorable moments. Or, head to Le Parisien Wine Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Las Volta Cocktailbar is perfect for those looking to extend their night with a touch of local flavor.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip 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 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 well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and picturesque spots. Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Leaning Tower Of Pisa is the first of them. Spend some time admiring this breathtaking monument before continuing your journey. Piazza Del Duomo, Pisa is your next stop. This iconic public square is one of the best-rated sights in Pisa.

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 Pisa Cathedral. This breathtaking church is a sight to behold. To round off your sightseeing experience, visit Spiaggia Pubblica Di Priaruggia.

At the end of the day, you will drive to Milan, 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 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.

Dine in style at Ristorante la Brisa, a top recommendation for dinner tonight. Or, for a change of pace, Pasticceria San Carlo boasts a menu that's sure to impress. Also, be sure to check out UNAHOTELS Cusani Milano. Known as a local hotspot, it’s a great choice for tonight in Milan.

Round off your dining experience by visiting Qc Termemilano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yguana Cafè, a bar catering to every mood and preference.

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