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’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 picture-perfect 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 impressive Galleria Vittorio Emanuele Ii. If you’re looking for more, Duomo Di Milano Museum is also a world-famous 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.

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 harmony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Known for its 3-star Michelin status, Enrico Bartolini al Mudec offers a delightful variety of dishes highlighting its delicious creative menu. If you're seeking an alternative culinary experience, be sure to explore Seta by Antonio Guida, a highly recommended restaurant known for its enticing international and contemporary 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 Il Luogo Aimo e Nadia, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and modern menu.

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

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

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

Savor the day by visiting some of the best places to see in Milan, including a museum, a beach, a castle, an archeological site and much more! Start your adventure at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This popular museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Beach Brema Sirmione located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Scaliger Castle. Its history-steeped features will captivate you. After the castle, continue your tour of the city with a visit to Archaeological Site Of Grotte Di Catullo. Visitors usually appreciate the history-steeped features of this archeological site.

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

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.

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.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Verona. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 1 night.

A blend of fun adventures, scenic views, and picturesque spots await you in Milan on today’s itinerary. First up is the locally renowned museum, Castelvecchio Museum. Afterward, continue to Verona Arena, a stadium every traveler should visit.

As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Delle Erbe. This popular public square is an essential stop. Following that, head to Museo Archeologico Al Teatro Romano, another must-visit site that will enhance your experience.

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.

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.

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

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.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the world-famous Rialto Bridge, a romantic historical landmark in Venice. Next, go to Piazza San Marco.

After visiting Rialto Bridge and Piazza San Marco, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to St Mark's Basilica. This visually striking church offers a unique experience. Doge's Palace is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Bridge Of Sighs, one of the most UNESCO world heritage-listed places to visit in Venice.

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.

Treat yourself to a wonderful meal at Veganda, a top-rated dining spot in Padua. If you're in the mood for something new, try Osteria Ai Scarponi, another premier location with a delectable menu. You might also want to book a table at Bamboo Cafe (Mma Silvestrin Snc Di Matteo & C). Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Padua.

After savoring a delicious meal, step into the vibrant nightlife at Il Gottino - Wine Bar, where the evening is just getting started. In the same way, Brutal offers a unique charm perfect for experiencing the local bar scene in Padua. Al Buscaglione is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 6 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Padua and Bologna. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Prepare for a day full of family-friendly attractions, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Ragione Palace. This increasingly popular palace is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is The Basilica Of St. Anthony, one of the city’s best highlights.

Next, check out Two Towers, one of the most popular places to see in Padua. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Maggiore. Wander around and soak in the culturally significant atmosphere this public square offers.

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

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Vatican City. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Start by visiting Sistine Chapel, a prime spot to begin your journey.

We also recommend visiting Vatican Museums, a globally renowned art museum.

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.

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.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended place to eat in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition and a delicious mediterranean and creative menu.

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio 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 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 for a day filled with fun adventures, scenic views, and picturesque spots in the charming city of Rome. Your adventure starts at Altare Della Patria, a captivating local hot spot. Another notable attraction to explore is Trevi Fountain. This iconic monument is known for its noteworthy 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 Piazza Di Spagna. This romantic public square offers a fascinating experience that many visitors find memorable. Spanish Steps is also worth visiting, along with Piazza Del Popolo. 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.

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.

Enjoy a delicious meal 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.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Relax and recharge in preparation for another adventurous day 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.

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 notable place to see in Rome. Then, wander over to Largo Di Torre Argentina. If historic sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Pantheon. This photogenic 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 astonishing 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 majestic Castel Sant'angelo. Take a moment to appreciate the fascinating details of this top-rated 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.

Treat yourself to a wonderful meal at Hotel de Russie, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at The Parrot Bar. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

After savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene in Rome.

Raise your glass to another unforgettable day in Italy!

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Rome, 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 Florence. You’ll stay here for 2 nights.

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Roman Forum. This timeless archeological site is a historic place to see in Rome. Continue your discovery at Colosseum, a culturally significant archeological site with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Navona. This iconic public square offers a majestic encounter with Rome. Next, make your way to Villa Borghese to add another highlight to your day. After that, visit Auditorium Parco Della Musica, a locally renowned concert hall that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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.

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

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.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

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

On day 11 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in Florence. Begin your sightseeing with Piazza Della Signoria. This spectacular public square is one of the top attractions in the city. Proceed to Palazzo Vecchio, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Uffizi Gallery. This famous art gallery is a traveler-favorite. Not far away, you’ll find Ponte Vecchio, another key site on your sightseeing itinerary. Piazzale Michelangelo 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.

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

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.

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

On day 12 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Pisa, where you’ll be staying for 1 night.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Basilica Of Santa Croce In Florence is the perfect place to start. This church is one of the most locally renowned places to visit in Florence. Next, head to Cathedral Of Santa Maria Del Fiore, a famous church, known for its romantic 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 Galleria Dell'accademia. This instagrammable art gallery is a highly recommended experience. Nearby, you'll also find Central Market. Visit these for an interesting touch to your journey.

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.

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

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Mercante, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Extend your evening after a delightful meal by visiting Jeffer Cocktails & Friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta Cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 adventure in Pisa promises more breathtaking discoveries and enriching experiences! Begin at Leaning Tower Of Pisa. This breathtaking monument is a highlight of any visit in the city. Then, enjoy Piazza Del Duomo, Pisa, another UNESCO world heritage-designated attraction that never fails to captivate visitors. Next, head over to Pisa Cathedral, one of the city’s most often recommended attractions, known for its historic features.

If you’re looking for more, spend time soaking in the atmosphere of Spiaggia Pubblica Di Priaruggia. This romantic beach is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

Have a fantastic dining experience at Ristorante la Brisa, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasticceria San Carlo offers an enticing alternative with its varied menu. Additionally, UNAHOTELS Cusani Milano is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

Explore the vibrant nightlife at Qc Termemilano after your meal, a hub for lively evenings and memorable moments. Or, head to Yguana Cafè for a great selection of flavorful drinks and a charming setting.

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