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 discover what to see in Milan. You’ll stay in Milan for 2 nights.

Start your day at Parco Sempione. This romantic park is a spectacular place to see in Milan. Then, wander over to Sforzesco Castle Art Library. If picture-perfect sites excite you, this castle will be right up your alley. Nearby, you’ll also find La Scala. This history-steeped opera house is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Galleria Vittorio Emanuele Ii is a top-rated spot in the city that will captivate you with its unique charm. When you’re done at the shopping mall, don’t forget to check out the enchanting Duomo Di Milano Museum. Take a moment to appreciate the fascinating details of this globally renowned church.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

Enjoy an outstanding dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an exceptional creative menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Seta by Antonio Guida, known for its delicious international and contemporary cuisine. Another highly-recommended place to eat in Milan is Il Luogo Aimo e Nadia, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious italian contemporary and modern menu.

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.

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

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

Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is an ideal stop early in the day. This interesting museum is a must-visit in the city.

Embrace the thrill of the open road as you wave goodbye to Milan and set your GPS to Sirmione. 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 40 min. Upon reaching Sirmione, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Beach Brema Sirmione is a frequently visited beach we recommend visiting today. Discover its serene features before continuing your self-guided tour to Scaliger Castle, a history-steeped castle that’s well-regarded in the area.

Next, stop by Archaeological Site Of Grotte Di Catullo, a history-steeped archeological site.

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

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

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.

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!

Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll spend 1 night.

Continue your road trip and head to your next destination, Verona. This car ride takes around 2 hours 4 min.

Our first attraction recommendation in Verona is Castelvecchio Museum, a captivating museum that draws attention for its standout features. Spend some time soaking in the atmosphere before continuing to Verona Arena, a grand stadium that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Piazza Delle Erbe, a well-known public square that offers a unique experience. Be sure to also explore Museo Archeologico Al Teatro Romano, a nearby museum, highly recommended by other travelers.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Venice. Venice 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 Venice's most popular restaurants, and connect with friendly locals for a true cultural experience.

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.

Cap off your dinner by heading to Al Parlamento, ideal for a leisurely evening with a drink in hand. The Caffe Rosso is another bar that offers an enjoyable setting. Similarly, Adagio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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

No visit to Venice is complete without Rialto Bridge. This world-famous historical landmark is one of the top attractions in the city. Proceed to Piazza San Marco, another must-visit attraction.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to St Mark's Basilica. This captivating church is a traveler-favorite. Not far away, you’ll find Doge's Palace, another key site on your sightseeing itinerary. Bridge Of Sighs is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

When you’re done exploring for the day, you’ll drive to your hotel in Padua. Check in and relax 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 Padua. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Don’t miss out on dining 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.

Continue your lively evening at Il Gottino - Wine Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Brutal is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Al Buscaglione ensures a night out tailored to your taste.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Padua and Bologna. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

Ragione Palace leaves a lasting impression. This palace is one of the most locally appreciated places to visit in Padua. Next, head to The Basilica Of St. Anthony, a notable church, known for its culturally significant features.

Set your GPS to Bologna and hit the road. Expect a journey of approximately 1 hour 34 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Bologna beckons with new experiences!

Our first attraction recommendation in Bologna is Two Towers, a popular monument that draws attention for its picture-perfect features. Spend some time soaking in the atmosphere before continuing to Piazza Maggiore, a romantic public square that stands out in the city.

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 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.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

Relax and look forward to more memorable moments to come!

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 3 nights.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Vatican City, Vatican City. Witness the landscapes transform as you cross the border to Vatican City. This drive usually takes around 2 hours 40 min.

One of our top recommendations for your sightseeing is Sistine Chapel. Then, head to St. Peter's Basilica. This iconic major basilica is a traveler-favorite in the city.

If you're keen to see more, continue to Saint Peter's Square. Feed your curiosity by learning something new about the square. Next, take your journey to Vatican Museums, an iconic art museum.

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

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.

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Head back to your accommodation in Rome and get some rest to prepare for another magical day of your road trip 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 the city and use the provided itinerary to discover what to see in Rome.

Altare Della Patria leaves a lasting impression. This monument is one of the most notable places to visit in Rome. Next, head to Trevi Fountain, a world-famous monument, 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 Piazza Di Spagna. This history-steeped public square is a highly recommended experience. Nearby, you'll also find Spanish Steps and Piazza Del Popolo Visit these for an interesting touch to your journey.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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

Head back to your accommodation in Rome and get some rest to prepare for another magical day of your road trip in Italy.

Day 9 offers an itinerary packed with the best things to see in Milan. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Your adventure in Rome is only getting started when you visit Circus Maximus, a locally renowned local hot spot. Another notable attraction to explore is Largo Di Torre Argentina. This captivating archeological site is known for its historic 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 Pantheon. This culturally significant monument offers a fascinating experience that many visitors find memorable. Campo De' Fiori is also worth visiting, along with Castel Sant'angelo. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Rome, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

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

On day 10 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Rome are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Roman Forum brings Rome's character to life. This culturally significant archeological site is a highlight of any visit in the city. Then, enjoy Colosseum, another culturally significant attraction that never fails to captivate visitors. Next, head over to Piazza Navona, one of the city’s most world-famous attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Villa Borghese. This mesmerizing park is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Auditorium Parco Della Musica, an interesting concert hall, and take a stroll around the area.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and international cuisine in the city.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

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

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

Check out the astonishing public square, Piazza Della Signoria. Afterward, continue to Palazzo Vecchio, a palace every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Uffizi Gallery. This top-rated art gallery is an essential stop. Following that, head to Ponte Vecchio, another must-visit site that will enhance your experience. Don’t forget to stop by Piazzale Michelangelo, a spectacular observation deck in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

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

Your itinerary for day 12 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Pisa, where you'll spend 1 night.

Basilica Of Santa Croce In Florence is perfect for a self-paced visit during the day. This culturally significant church is sure to impress. Next on your list is Cathedral Of Santa Maria Del Fiore, another must-visit landmark and widely recognized church renowned for its enchanting features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Galleria Dell'accademia. This respected art gallery is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Central Market, a well-known food market.

At the end of the day, you will drive to Pisa, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Pisa, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining spot in Pisa. If you're in the mood for something new, try il Mercante, another premier location with a delectable menu. You might also want to book a table at La Ghiotteria. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

After your meal, keep the night alive at a bar like Jeffer Cocktails & Friends, known for its lively atmosphere. Le Parisien Wine Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Las Volta Cocktailbar offers an excellent atmosphere for those looking to amp up the evening.

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

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

Awaiting your discovery is the globally renowned Leaning Tower Of Pisa, a picture-perfect monument in Pisa. Next, go to Piazza Del Duomo, Pisa.

After visiting Leaning Tower Of Pisa and Piazza Del Duomo, Pisa, have a stroll along Pisa's streets and take in the local charm. Continue your sightseeing by heading to Pisa Cathedral. This grand church offers a unique experience.

When you’re ready to jump back into the car and say goodbye to Pisa, you’ll hit the road in the direction of Genoa. This drive usually takes around 1 hour 43 min.

One of our top recommendations for your sightseeing is Spiaggia Pubblica Di Priaruggia. Spend some time admiring the romantic features of the beach before you continue to your next stop.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Milan. Milan 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 Milan's most popular restaurants, and connect with friendly locals for a true cultural experience.

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.

Continue your evening by exploring the vibrant nightlife scene at Qc Termemilano, a prime destination for a thrilling night out. Also, don’t forget to check out Yguana Cafè, a bar that offers unique local touches.

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