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.

Today’s agenda in Milan includes a park, a castle, an opera house, a shopping mall, a church and much more! Parco Sempione is must-visit park and a great starting point for the day. Next, continue your journey to Sforzesco Castle Art Library, a top-rated castle, located just a leisurely stroll away. Next, head to La Scala, a romantic opera house, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Milan. When you're ready, let your sightseeing route take you to the famous Galleria Vittorio Emanuele Ii. If you’re looking for more, Duomo Di Milano Museum is also a globally renowned attraction that is worthwhile a visit.

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

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.

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and modern cuisine in the city.

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Milan for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Milan and Sirmione.

Milan is brimming with adventures. Today’s wonderful stops include a museum, a beach, a castle, an archeological site and much more! Begin your sightseeing adventure at the well-known Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" 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 spectacular spots that you shouldn’t miss. Another great site to visit is the popular 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 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.

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.

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

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

Today’s well-planned self-sightseeing route offers several family-friendly attractions, scenic views, and picturesque spots. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Castelvecchio Museum is the first of them. Spend some time admiring this stunning museum before continuing your journey. Verona Arena is your next stop. This world-famous stadium is one of the best-rated sights in Milan.

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 Delle Erbe. This enchanting public square is a sight to behold. To round off your sightseeing experience, visit Museo Archeologico Al Teatro Romano.

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

Prepare for an extraordinary culinary adventure in Venice by booking a table at Local, a 1-star Michelin restaurant that boasts an exceptional contemporary menu. For a different flavor experience, head to Wistèria, renowned for its delectable contemporary and venetian dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Quadri, a local gem known for its delightful modern cuisine in Venice. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Keep the excitement of the evening going by visiting a bar or two. Al Parlamento is an excellent place to start. You could also check out The Caffe Rosso, offering a different kind of charm. A last recommendation for the day is Adagio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass and celebrate another amazing 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.

Venice is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Rialto Bridge, a timeless historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Piazza San Marco, enchanting visitors with its history-steeped appeal. Continue your exploration at St Mark's Basilica. This church is one of the city’s most popular spots.

Enjoy the freedom of exploring Venice at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Doge's Palace. After exploring the palace, head to the well-known Bridge Of Sighs.

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.

As you explore more of Padua, 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 Veganda, a top-rated dining destination in Padua. If you're in the mood to try something new, consider Osteria Ai Scarponi, another top spot with a mouthwatering 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 a perfect choice to enhance your stay in Padua this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Il Gottino - Wine Bar, known for its inviting atmosphere. Brutal is another great option if you’re looking for a place to get the night started. Similarly, Al Buscaglione provides a great setting to enjoy the night away.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Padua and Bologna. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 1 night.

Get ready to discover some of the most iconic wonders in Padua, including a palace, a church, a monument, a public square and much more! Start your day at Ragione Palace. This historic palace is an often recommended place to see in Padua. Then, wander over to The Basilica Of St. Anthony. If heritage-rich sites excite you, this church will be right up your alley. Nearby, you’ll also find Two Towers. This stunning monument is a favorite among visitors.

Padua offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Maggiore is a top-rated spot in the city that will captivate you with its unique charm.

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.

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

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.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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 7 of your remarkable road trip in Italy. Today you will explore Vatican City, 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 Rome. You’ll stay here for 3 nights.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Sistine Chapel is the perfect place to start. This chapel is one of the most extraordinary places to visit in Siena.

Nearby, you'll also find Vatican Museums. Visit these for an interesting touch to your journey.

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 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.

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative and innovative 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 Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean and creative menu.

After your meal, keep the night alive at a bar like La Botticella Of Poggi Giovanni, known for its lively atmosphere. Almalu Trastevere is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Viminale Di Pepi Maurilio offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

Day 8 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

Discover a day packed with family-friendly attractions, breathtaking views, and picturesque spots in Rome. Begin your sightseeing with Altare Della Patria. This notable monument is one of the top attractions in the city. Proceed to Trevi Fountain, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Di Spagna. This wondrous public square is a traveler-favorite. Not far away, you’ll find Spanish Steps, another key site on your sightseeing itinerary. Piazza Del Popolo is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

Treat yourself to a delightful dinner at RomAntica, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Coso Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at DEROMA - Farine Romane as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Cap off your dinner by heading to Sant' Eustachio Caffè, ideal for a leisurely evening with a drink in hand. Yellowsquare Rome is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the well-known Circus Maximus, a breathtaking archeological site in Rome. Next, go to Largo Di Torre Argentina.

After visiting Circus Maximus and Largo Di Torre Argentina, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Pantheon. This photogenic monument offers a unique experience. Campo De' Fiori is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Castel Sant'angelo, one of the most enchanting places to visit in Rome.

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

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.

Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

To truly maximize your evening out, consider visiting The Apartment Bar Roma after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Hotel Hassler Roma, another bar with an inviting ambiance.

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.

On day 10 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 Rome. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, scenic views, and picturesque spots. Start at Roman Forum, a world-famous archeological site in the city. Then, head to Colosseum and soak in the ambiance of this UNESCO world heritage-designated archeological site.

There are many interesting places to see in Rome, and when you are ready for more, go to Piazza Navona. This is one of the city’s most timeless visually striking spots of interest. After exploring the public square, visit the widely recognized Villa Borghese. Not far away, you'll also find Auditorium Parco Della Musica. This concert hall is an eye-catching highlight in Rome.

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.

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 11 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and breathtaking views. Start at Piazza Della Signoria, a famous public square in the city. Then, head to Palazzo Vecchio and soak in the ambiance of this enchanting palace.

There are many interesting places to see in Florence, and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most widely recognized picture-perfect spots of interest. After exploring the art gallery, visit the world-famous Ponte Vecchio. Not far away, you'll also find Piazzale Michelangelo. This observation deck is a visually striking highlight 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.

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.

Don’t miss out on dining 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.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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.

Get ready for a day filled with fun adventures, photo-friendly spots, and history-rich sites in the charming city of Florence. Your adventure starts at Basilica Of Santa Croce In Florence, a notable local hot spot. Another notable attraction to explore is Cathedral Of Santa Maria Del Fiore. This widely recognized church is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Galleria Dell'accademia. This photogenic art gallery offers a fascinating experience that many visitors find memorable. Central Market is also worth visiting.

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.

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

Savor the flavors at Anima di Grano Pizzeria Napoletana Pisa Italy, a top pick for dinner tonight. Alternatively, il Mercante beckons with its unique menu offerings. Also, consider La Ghiotteria. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

Unwind after your meal by stepping into Jeffer Cocktails & Friends. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Le Parisien Wine Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Las Volta Cocktailbar, another top-rated bar in the area.

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

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.

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 wondrous 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 frequently visited spots that you shouldn’t miss. Another great site to visit is the locally appreciated 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.

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.

Make sure to reserve a table at Ristorante la Brisa, 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 Pasticceria San Carlo, 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 UNAHOTELS Cusani Milano, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Qc Termemilano, ideal for a leisurely evening with a drink in hand. Yguana Cafè is another bar that offers an enjoyable setting.

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