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

Day 2 offers a multitude of experiences. You will stay in Milan for 2 nights more, offering you enough time to explore at a relaxed pace.

Get ready for a day filled with fun adventures, romantic experiences, and natural wonders in the charming city of Milan. Your adventure starts at Parco Sempione, a spectacular local hot spot. Another notable attraction to explore is Sforzesco Castle Art Library. This famous castle is known for its romantic 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 La Scala. This historic opera house offers a fascinating experience that many visitors find memorable. Galleria Vittorio Emanuele Ii is also worth visiting, along with Duomo Di Milano Museum. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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

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

Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary 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 Il Luogo Aimo e Nadia, 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 modern cuisine in the city.

If you’re not ready to end the night just yet, Kilburn Cocktail Bar Milano offers a perfect venue to relax and savor a drink. Similarly, Bar Frida is well-suited for those looking to unwind in a social setting. The Friends Pub Milano is another excellent spot to enjoy a nightcap after a delightful meal.

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

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Milan, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Start your day at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This instagrammable museum is a captivating place to see in Milan.

Continue your road trip and head to your next destination, Sirmione. This car ride takes around 1 hour 40 min.

Savor the rest of your day by heading to Beach Brema Sirmione, an often recommended beach that draws visitors from near and far. When you're done, continue on to Scaliger Castle, where you can soak in the majestic surroundings. Next, explore Archaeological Site Of Grotte Di Catullo, yet another notable place to see in the area.

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.

Treat yourself to a wonderful meal at Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

If you’re not ready to end the night just yet, Bhangrabar offers a perfect venue to relax and savor a drink. Similarly, Rufus Cocktail Bar is well-suited for those looking to unwind in a social setting. Ostello Bello Grande is another excellent spot to enjoy a nightcap after a delightful meal.

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Verona. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Venice. You will spend 1 night here for some well-deserved relaxation.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Verona. Your travel time is around 2 hours 4 min.

One of our top recommendations for your sightseeing is Castelvecchio Museum. Spend some time admiring the instagrammable features of the museum before you continue to your next stop. Then, head to Verona Arena. This globally renowned stadium is a traveler-favorite in the city. Not far away, you’ll also find Piazza Delle Erbe. Feed your curiosity by learning something new about the public square. Next, continue your journey to Museo Archeologico Al Teatro Romano, an often recommended museum.

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.

Begin your culinary exploration in Venice by securing a reservation at Local. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of contemporary cuisine. For another dining delight, visit Wistèria, celebrated for its delectable contemporary and venetian menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Quadri, a top local spot known for its tantalizing modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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.

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Venice. When you’re not sightseeing, take time to relax at your selected hotel in Padua, where you’ll be staying for 1 night.

A blend of family-friendly attractions, romantic experiences, and scenic views await you in Venice on today’s itinerary. First up is the wondrous historical landmark, Rialto Bridge. It's a standout spot that offers a memorable visit. Afterward, continue to Piazza San Marco. A visit to this public square is an enriching experience for all.

As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to St Mark's Basilica. This locally renowned church is an essential stop that should not be missed. Following that, head to Doge's Palace, another must-visit site that will enhance your experience. Lastly, visit Bridge Of Sighs and learn why this monument is renowned as one of the city's most well-known attractions.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Padua. Padua offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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

Make sure to reserve a table at Veganda, an iconic dining spot in Padua. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Ai Scarponi, a popular restaurant in Padua. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bamboo Cafe (Mma Silvestrin Snc Di Matteo & C), a hidden gem nestled in Padua. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Il Gottino - Wine Bar, a top-rated bar in the area. For other recommendations, Brutal provides a perfect setting for rounding out your night with style and great drinks. Likewise, Al Buscaglione offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences 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.

Get ready for a day filled with family-friendly attractions, breathtaking views, and picturesque spots in the charming city of Padua. Your adventure starts at Ragione Palace, an often recommended local hot spot. Another notable attraction to explore is The Basilica Of St. Anthony. This locally renowned church is known for its historic appeal.

Fasten your seatbelt and make your way to your next stop. Bologna, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Padua to Bologna may take around 1 hour 34 min without traffic disruptions. Upon arrival in Bologna, we highly recommend checking out some of the top attractions.

Head to Two Towers, a well-known monument in Bologna. Explore its breathtaking features at your own pace before you continue your journey to your next sight, Piazza Maggiore. This extraordinary public square is a top recommendation in the area.

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 explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Don’t miss out on dining at 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.

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

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

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.

As you’ve unraveled the marvels of Siena, it’s time to gear up for the next part of your road trip adventure. Set course for Vatican City! Under favorable conditions, your drive to Vatican City may take around 2 hours 40 min. Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Head to Sistine Chapel, an impressive chapel in Vatican City. This globally renowned major basilica is a top recommendation in the area. When you’re ready to explore more, Saint Peter's Square is an excellent choice. Next, continue your sightseeing at the timeless Vatican Museums and discover what makes this art museum unique.

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.

Treat yourself to an extraordinary dining experience at La Pergola, a 3-star Michelin restaurant offering an incredible mediterranean and contemporary menu. Alternatively, if your taste buds call for something different, Il Pagliaccio is one of the best restaurants for creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Enoteca La Torre. As a top-rated establishment with 2 Michelin star, it is an ideal choice for mediterranean and creative cuisine in the city.

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.

Prepare for a day full of family-friendly attractions, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Altare Della Patria. This notable monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Trevi Fountain, one of the city’s most promising highlights.

Next, check out Piazza Di Spagna, one of the most iconic places to see in Rome. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Spanish Steps. Wander around and soak in the history-steeped atmosphere this public square offers. Finally, take the path to the spectacular Piazza Del Popolo, the last of our attraction recommendations for today.

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.

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable day 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.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Circus Maximus. This culturally significant archeological site is a highlight of any visit in the city. Then, enjoy Largo Di Torre Argentina, another historic attraction that never fails to captivate visitors. Next, head over to Pantheon, one of the city’s most world-famous attractions, known for its photogenic features.

If you’re looking for more, spend time soaking in the atmosphere of Campo De' Fiori. This romantic public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Castel Sant'angelo, an extraordinary castle, and take a stroll around the area.

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

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.

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.

Let the evening flow smoothly from dinner to drinks at The Apartment Bar Roma, a top-rated bar in the area. For other recommendations, Hotel Hassler Roma provides a perfect setting for rounding out your night with style and great drinks.

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

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Roman Forum. This picture-perfect archeological site is sure to ignite your curiosity. Next, dive into the picture-perfect features of Colosseum, a must-visit archeological site in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Piazza Navona, an iconic public square. For a change of scene, check out Villa Borghese, known for its eye-catching features.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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.

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

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

Get ready to discover some of the most iconic wonders in Florence, including a public square, a palace, an art gallery, a historical landmark, an observation deck and much more! Start your day at Piazza Della Signoria. This remarkable public square is an impressive place to see in Florence. Then, wander over to Palazzo Vecchio. If history-steeped sites excite you, this palace will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This romantic art gallery is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Ponte Vecchio is a globally renowned spot in the city that will captivate you with its unique charm. When you’re done at the historical landmark, don’t forget to check out the romantic Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this impressive 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.

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.

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

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

Experience an unparalleled adventure on day 12 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pisa. You will spend 1 night here for some well-deserved relaxation.

Savor the day by visiting some of the best places to see in Florence, including a church, an art gallery, and a food market. Start your adventure at Basilica Of Santa Croce In Florence. This captivating church is a must-visit for travelers looking for a unique holiday experience. Make your way to Cathedral Of Santa Maria Del Fiore located in Florence for an enchanting atmosphere.

Next, immerse yourself in the setting of Galleria Dell'accademia. Its respected features will captivate you. After the art gallery, continue your tour of the city with a visit to Central Market. This food market has a picture-perfect appeal.

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

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.

Keep the evening going at Jeffer Cocktails & Friends, a great choice for enjoying the after-dinner hours with a drink. You could also go to Le Parisien Wine Bar, which offers a similarly pleasant setting and great drinks. Another option is Las Volta Cocktailbar, which provides an inviting environment for unwinding after a busy day out.

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

On day 13 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Genoa. When you’re not sightseeing, take time to relax at your selected hotel in Milan, where you’ll be staying for 1 night.

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

Embrace the thrill of the open road as you wave goodbye to Pisa and set your GPS to Genoa. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 43 min. Upon reaching Genoa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Savor the rest of your day by heading to Spiaggia Pubblica Di Priaruggia, a worthwhile beach that draws visitors from near and far.

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.

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.

Following your dinner, dive into the local bar culture at Qc Termemilano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yguana Cafè, the perfect place for those looking to experience the best of the nightlife.

Raise your glass and celebrate another amazing day of your road trip in Italy!