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

Day 2 offers an itinerary packed with the best things to see in Milan. You’ll stay in Milan for 2 nights more, offering you enough time to explore at a relaxed pace.

Catch Parco Sempione before the crowds roll in. This romantic park is sure to ignite your curiosity. Next, dive into the picture-perfect features of Sforzesco Castle Art Library, a must-visit castle 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 La Scala, an interesting opera house. For a change of scene, check out Galleria Vittorio Emanuele Ii, known for its enchanting features. We also recommend visiting Duomo Di Milano Museum. This church is a must for anyone looking to experience the city to the fullest.

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.

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary 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 Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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.

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

Wake up to day 3 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Milan and Sirmione. With 1 night to stay in Milan, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Your adventure in Milan is only getting started when you visit Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a well-known local hot spot. Another notable attraction to explore is Beach Brema Sirmione. This often recommended beach is known for its photogenic appeal.

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

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

Milan 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 Milan.

Dine in style at Bice Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, Alto Ristorante boasts a menu that's sure to impress. Also, be sure to check out Nero 9. Known as a local hotspot, it’s a great choice for tonight in Milan.

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 day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip 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 place, which are Verona. At the end of the day, you will retreat to the hotel of your choice in Venice, where will spend 1 night.

Awaiting your discovery is the notable Castelvecchio Museum, a history-steeped museum in Milan. Next, go to Verona Arena.

After visiting Castelvecchio Museum and Verona Arena, have a stroll along Milan's streets and take in the local charm. Continue your sightseeing by heading to Piazza Delle Erbe. This enchanting public square offers a unique experience. Museo Archeologico Al Teatro Romano is another noteworthy attraction worthwhile a visit.

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.

Get ready for an unforgettable culinary journey in Venice by reserving a table at Local. Renowned as a 1-star Michelin restaurant, it offers an exceptional contemporary menu. For a different taste experience, head to Wistèria, recognized for its delicious contemporary and venetian dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Quadri, a local favorite known for its delightful modern cuisine in Venice. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for modern foodies seeking culinary excellence.

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

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.

Visiting Rialto Bridge is always a good idea. This wondrous historical landmark is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the UNESCO world heritage-listed wonders of Piazza San Marco, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to St Mark's Basilica. This well-known church offers an enriching experience. For a change of pace, head to Doge's Palace, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Bridge Of Sighs. These sights offer a fulfilling end to a perfect day.

At the end of the day, you will drive to Padua, 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 Padua, it's often a good idea to reserve a table in advance.

Dine in style at Veganda, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Ai Scarponi boasts a menu that's sure to impress. Also, be sure to check out Bamboo Cafe (Mma Silvestrin Snc Di Matteo & C). Known as a local hotspot, it’s a great choice for tonight in Padua.

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.

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

Your itinerary for day 6 of your road trip in Italy includes 2 stops and features some of the highlights of Padua and Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 1 night.

No visit to Padua is complete without Ragione Palace. This curiosity-inducing palace is one of the top attractions in the city. Proceed to The Basilica Of St. Anthony, another must-visit attraction.

As you wander through the inviting streets of Padua, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Two Towers. This captivating monument is a traveler-favorite. Not far away, you’ll find Piazza Maggiore, another key site on your sightseeing itinerary.

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

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

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise your glass to another unforgettable day in Italy!

On day 7 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Vatican City are on today's agenda. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

Experience Sistine Chapel, an impressive chapel in the city.

After exploring the square, visit the wondrous Vatican Museums.

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.

Rome 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 Rome.

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Following your dinner, dive into the local bar culture at La Botticella Of Poggi Giovanni. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Almalu Trastevere, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Relax and look forward to more memorable moments to come!

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 popular places to visit in Rome. Next, head to Trevi Fountain, a timeless monument, known for its visually striking 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 symbolic 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.

Rome 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 Rome.

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.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Rome is brimming with adventures.

Circus Maximus brings Rome's character to life. This standout archeological site is a highlight of any visit in the city. Then, enjoy Largo Di Torre Argentina, another respected attraction that never fails to captivate visitors. Next, head over to Pantheon, one of the city’s most timeless attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Campo De' Fiori. This history-steeped 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 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 Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely dining experience at Hotel de Russie, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at La Taverna Italiana, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated The Parrot Bar. It’s yet another ideal choice to enhance your time in Rome tonight.

Keep the excitement of the evening going by visiting a bar or two. The Apartment Bar Roma is an excellent place to start. You could also check out Hotel Hassler Roma, offering a different kind of charm.

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

Dive into day 10 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Rome. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 2 nights.

Roman Forum is must-visit archeological site and a great option for a daytime tour of the area. Continue your journey to Colosseum, a world-famous archeological site, located just a leisurely stroll away. Next, head to Piazza Navona, an enchanting public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the widely recognized Villa Borghese. If you’re looking for more, Auditorium Parco Della Musica is also a well-known attraction that is worthwhile a visit.

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

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.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. Known for great service, it’s a fantastic choice for tonight in Florence.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

On day 11 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 1 night.

Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Experience Piazza Della Signoria, a top-rated public square in the city. Then, head to Palazzo Vecchio and soak in the ambiance of this history-steeped 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 top-rated romantic spots of interest. After exploring the art gallery, visit the iconic Ponte Vecchio. Not far away, you'll also find Piazzale Michelangelo. This observation deck is an awe-inspiring highlight in Florence.

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

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable 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 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Pisa, where will spend 1 night.

Whatever your travel style is, Basilica Of Santa Croce In Florence is an essential stop in Florence. This well-known church provides an insightful glimpse into the city's identity. Next, discover Cathedral Of Santa Maria Del Fiore, an enchanting church, promising a delightful encounter.

Continue your sightseeing with a visit to Galleria Dell'accademia, a well-known art gallery. When you’re done, don’t forget to make a stop at the well-known Central Market.

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

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

Don’t miss out on dining at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

Keep the excitement of the evening going by visiting a bar or two. Jeffer Cocktails & Friends is an excellent place to start. You could also check out Le Parisien Wine Bar, offering a different kind of charm. A last recommendation for the day is Las Volta Cocktailbar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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, 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.

To truly experience Pisa, make sure to drop by Leaning Tower Of Pisa. This wondrous monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Duomo, Pisa, one of the city’s best highlights.

Next, check out Pisa Cathedral, one of the most worthwhile places to see in Pisa. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Spiaggia Pubblica Di Priaruggia. Wander around and soak in the mesmerizing atmosphere this beach offers.

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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Qc Termemilano stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yguana Cafè offers an ideal atmosphere to enjoy the pleasures of the night.

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